1-Phenyl-1,2-propanediol [C9H12O2]

1-Phenyl-1,2-propanediol [C9H12O2]

Query Query

Results

Date

52 reactions in Reaxys

2018-08-07 14h:45m:35s (UTC)

HO

1. Query

HO

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='1855-09-0') AND (IDE.INCHI='MZQZXSHFWDHNOWUHFFFAOYSA-N') NOT (RX.RXRN=2044500))

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1-Phenyl-1,2-propanediol [C9H12O2]

HO O

HO

Rx-ID: 29082084 View in Reaxys 1/52 Yield

Conditions & References

Ca. 80 %Chromat.

With 4-tert-butylpyridine, dihydrogen peroxide, methyltrioxorhenium(VII) in water, tert-butyl alcohol, Time= 3h, T= 45 °C Altmann, Philipp; Kuehn, Fritz E.; Journal of Organometallic Chemistry; vol. 694; nb. 25; (2009); p. 4032 - 4035 View in Reaxys With [Mn2(1,4,7-tritosyl-1,4,7-triazacyclononane)2(μ-O)3](PF6)2.H2O, dihydrogen peroxide in water, acetonitrile, Time= 3h, T= 0 °C Schoenfeldt, Nicholas J.; Korinda, Andrew W.; Notestein, Justin M.; Chemical Communications; vol. 46; nb. 10; (2010); p.

1640 - 1642 View in Reaxys

44 %Chromat.

With magnesium(II) perchlorate hexahydrate, FeII(OTf)2(tris((5-(triisopropylsilyl)pyridin-2-yl)methyl)amine), dihydrogen peroxide in water, acetonitrile, Time= 1h, T= 0 °C , chemoselective reaction Borrell, Margarida; Costas, Miquel; Journal of the American Chemical Society; vol. 139; nb. 36; (2017); p. 12821 - 12829 View in Reaxys HO

O

O

HO

Rx-ID: 32053181 View in Reaxys 2/52 Yield 95 %

Conditions & References With sodium tetrahydroborate in ethanol, Time= 1h, T= 0 °C , Inert atmosphere Wang, Jun-Li; Li, Hui-Jing; Wang, Hong-Shuang; Wu, Yan-Chao; Organic Letters; vol. 19; nb. 14; (2017); p. 3811 - 3814 View in Reaxys With hydrogen, cinchonidine, acetic acid in water, T= 20 °C , p= 5171.62Torr , Autoclave Erathodiyil, Nandanan; Gu, Hongwei; Shao, Huilin; Jiang, Jiang; Ying, Jackie Y.; Green Chemistry; vol. 13; nb. 11; (2011); p. 3070 - 3074 View in Reaxys 2.6 Product identification General procedure: The reaction was conducted at 37°C in a 2.0-mL reaction mixture, containing coenzyme (1-mM NADP+ or 0.1-mM NADPH), substrate (0.05–0.1mM), enzyme (0.1–0.3mg), and 0.1-M potassium phosphate, pH 7.4. The substrate and products were extracted into 4-mL ethyl acetate 30min after the reaction was started at 37°C. The products of oxidoreduction of steroids [25] and reduction of PGD2 [28], farnesal [29] and 4-oxo-2-nonenal [18] were analyzed by TLC, as described. The reduced products of TBE were identified by the HPLC methods [23]. The products of 3HB oxidation, 3OB reduction, 5βandrostane-3β,17β-diol oxidation and 5β-androstan-3β-ol-17-one reduction were analyzed by the liquid chromatography–electrospray ionization-mass spectrometry (LC–ESI-MS) using a Hewlett-Packard HP 1100 Series LC/MSD system attached with a diode array detector and a column (Mightysil RP-18 GP 5μm, 4.6mm×250mm, Kanto Chemical Co., Tokyo, Japan). Separations were carried out at a flow rate of 0.5mL/min and 40°C using the following mobile phases: 25percent acetonitrile aqueous solution containing 0.1percent formic acid for 3OB and β/β-3HBs, and 80percent acetonitrile aqueous solution containing 0.1percent formic acid for the two steroids. 3OB, β-3HB, β-3HB, 5β-androstan-3β-ol-17-one and 5β-androstane-3β,17β-diol were detected by monitoring their total ions (m/z 249.1, 251.1, 251.1, 289.4 and 291.4, respectively) in the negative ESI mode, and eluted at the retention times of 20.1, 17.6, 16.8, 14.9 and 12.7min, respectively. The detection limits of 3OB, β/β-3HBs and the two steroids were 0.1, 0.1 and 1nmol, respectively.

With rabbit 3-hydroxyhexobarbital dehydrogenase (AKR1C29), NADPH in aq. phosphate buffer, ethyl acetate, Time= 0.5h, T= 37 °C , pH= 7.4, Enzymatic reaction, Catalytic behavior, Kinetics

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1-Phenyl-1,2-propanediol [C9H12O2]

Endo, Satoshi; Matsunaga, Toshiyuki; Matsumoto, Atsuko; Arai, Yuki; Ohno, Satoshi; El-Kabbani, Ossama; Tajima, Kazuo; Bunai, Yasuo; Yamano, Shigeru; Hara, Akira; Kitade, Yukio; Biochemical Pharmacology; vol. 86; nb. 9; (2013); p.

1366 - 1375 View in Reaxys HO

HO O

Rx-ID: 46781267 View in Reaxys 3/52 Yield

Conditions & References Reaction Steps: 2 1.1: sodium hydride / tetrahydrofuran / 1 h / Reflux 1.2: Wittig Olefination / 0 °C / Reflux 2.1: 9-mesityl-10-methylacridinium perchlorate; sodium hydrogencarbonate / acetonitrile / 6 h / 20 °C / Irradiation 2.2: 3 h / 20 °C With sodium hydride, sodium hydrogencarbonate, 9-mesityl-10-methylacridinium perchlorate in tetrahydrofuran, acetonitrile, 1.1: |Wittig Olefination Yang, Bo; Lu, Zhan; Chemical Communications; vol. 53; nb. 94; (2017); p. 12634 - 12637 View in Reaxys HO

HO

Rx-ID: 46781329 View in Reaxys 4/52 Yield

Conditions & References

66 %

Stage 1: With sodium hydrogencarbonate, 9-mesityl-10-methylacridinium perchlorate in acetonitrile, Time= 6h, T= 20 °C , Irradiation Stage 2: With triphenylphosphine in acetonitrile, Time= 3h, T= 20 °C Yang, Bo; Lu, Zhan; Chemical Communications; vol. 53; nb. 94; (2017); p. 12634 - 12637 View in Reaxys

18O

HO

HO

O H 18O

HO

Rx-ID: 47373880 View in Reaxys 5/52 Yield

Conditions & References

32 %, 15 %, With [Fe(CF3SO3)2((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)], dihydrogen peroxide, [18O]water in acetonitrile, 68 % Time= 3h, T= 0 °C , Catalytic behavior Zima, Alexandra M.; Lyakin, Oleg Y.; Ottenbacher, Roman V.; Bryliakov, Konstantin P.; Talsi, Evgenii P.; ACS Catalysis; vol. 7; nb. 1; (2017); p. 60 - 69 View in Reaxys

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1-Phenyl-1,2-propanediol [C9H12O2]

HO

HO

O H 18O

HO

Rx-ID: 47373881 View in Reaxys 6/52 Yield 53 %, 47 %

Conditions & References With [Fe(CF3SO3)2((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)], [18O]water, 3-chloro-benzenecarboperoxoic acid in acetonitrile, Time= 3h, T= 0 °C , Catalytic behavior Zima, Alexandra M.; Lyakin, Oleg Y.; Ottenbacher, Roman V.; Bryliakov, Konstantin P.; Talsi, Evgenii P.; ACS Catalysis; vol. 7; nb. 1; (2017); p. 60 - 69 View in Reaxys HO

HO

Rx-ID: 1763948 View in Reaxys 7/52 Yield 100 %

Conditions & References With osmium(VIII) oxide, cinchona alkaloid on mesoporous SBA-15 silica support, Time= 24h, T= 0 °C Lee, Hong Myung; Kim, Sang-Wook; Hyeon, Taeghwan; Kim, B. Moon; Tetrahedron Asymmetry; vol. 12; nb. 11; (2001); p.

1537 - 1541 View in Reaxys

96 %

With 4-methylmorpholine N-oxide, Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4 in water, acetone, acetonitrile, T= 20 °C Choudary; Chowdari; Kantam; Raghavan; Journal of the American Chemical Society; vol. 123; nb. 37; (2001); p. 9220 9221 View in Reaxys

96 %

General procedure: To an acetone-H2O (2:1, v/v) solution (3 mL) of olefin (1 mmol) was added a magnetic osmium catalyst (0.02 mmol) and N-methylmorpholine N-oxide (NMO; 1.3 mmol) successively at room temperature under an argon atmosphere.

After stirring the resulting mixture, the dihydroxylation reaction was completed (monitored by TLC). After the reaction mixture was slightly evaporated to remove acetone, a magnetic osmium catalyst was separated by magnetic decantation using an external magnet followed by washing with H2O, and the recovered magnetic osmium catalyst was reused for subsequent dihydroxylation reactions.

With 4-methylmorpholine N-oxide in water, acetone, Time= 2h, T= 20 °C , Inert atmosphere Fujita, Ken-Ichi; Umeki, Satoshi; Yamazaki, Manabu; Ainoya, Taku; Tsuchimoto, Teruhisa; Yasuda, Hiroyuki; Tetrahedron Letters; vol. 52; nb. 24; (2011); p. 3137 - 3140 View in Reaxys

95 %

With water, 4-methylmorpholine N-oxide in dichloromethane, tert-butyl alcohol, Time= 8h, T= 20 °C , Inert atmosphere, Reagent/catalyst, Time, Concentration Fujita, Ken-Ichi; Umeki, Satoshi; Yasuda, Hiroyuki; Synlett; vol. 24; nb. 8; (2013); p. 947 - 950; Art.No: ST-2013-U0179-L View in Reaxys

91 %

With O4Os(2-)*C123H141N3O28 (2+), 4-methylmorpholine N-oxide in water, acetonitrile, Time= 0.5h, T= 20 °C , Inert atmosphere, Time, Reagent/catalyst Fujita, Ken-Ichi; Inoue, Kensuke; Tsuchimoto, Teruhisa; Yasuda, Hiroyuki; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 12; (2012); p. 1594 - 1598 View in Reaxys With water, osmium(VIII) oxide in acetone, Time= 5h, T= 0 °C , the kinetic role of the alkaloid (dihydroquinidine 4-chlorobenzoate), Mechanism Wai, John S. M.; Marko, Istvan; Svendsen, John, S.; Finn, M. G.; Jacobsen, Eric N.; Sharpless, K. Barry; Journal of the American Chemical Society; vol. 111; nb. 3; (1989); p. 1123 - 1125

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1-Phenyl-1,2-propanediol [C9H12O2]

View in Reaxys With dipotassium peroxodisulfate, silver nitrate in water, acetonitrile, T= 40 °C Citterio, Attilio; Arnoldi, Claudio; Giordano, Claudio; Castaldi, Grasiano; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1983); p. 891 - 896 View in Reaxys Ca. 90 %Chromat.

With N-(4-chlorophenyl)salicylaldimine, dihydrogen peroxide, methyltrioxorhenium(VII) in water, tert-butyl alcohol, Time= 3h, T= 25 °C Altmann, Philipp; Kuehn, Fritz E.; Journal of Organometallic Chemistry; vol. 694; nb. 25; (2009); p. 4032 - 4035 View in Reaxys Reaction Steps: 2 1: [Fe(OTf)2(mix-BPBP)]; dihydrogen peroxide / acetonitrile / 2.5 h / 0 °C 2: sulfuric acid / acetonitrile; water / 16 h / 20 °C With sulfuric acid, [Fe(OTf)2(mix-BPBP)], dihydrogen peroxide in water, acetonitrile Spannring, Peter; Yazerski, Vital; Bruijnincx, Pieter C. A.; Weckhuysen, Bert M.; Klein Gebbink, Robertus J. M.; Chemistry - A European Journal; vol. 19; nb. 44; (2013); p. 15012 - 15018 View in Reaxys HO

O

HO

Rx-ID: 36533964 View in Reaxys 8/52 Yield

Conditions & References With sulfuric acid in water, acetonitrile, Time= 16h, T= 20 °C Spannring, Peter; Yazerski, Vital; Bruijnincx, Pieter C. A.; Weckhuysen, Bert M.; Klein Gebbink, Robertus J. M.; Chemistry - A European Journal; vol. 19; nb. 44; (2013); p. 15012 - 15018 View in Reaxys HO

HO

Rx-ID: 9243366 View in Reaxys 9/52 Yield 94 %

Conditions & References With oxygen, 4-methylmorpholine N-oxide in water, acetone, Time= 2h, T= 25 °C Jun, Bong-Hyun; Kim, Jong-Ho; Park, Juyoung; Kang, Homan; Lee, Sang-Hyeup; Lee, Yoon-Sik; Synlett; nb. 15; (2008); p. 2313 - 2316 View in Reaxys

81 %

With osmium(VIII) oxide, 4-methylmorpholine N-oxide in water, acetone, Time= 3h, T= 20 °C Bales; Horner; Huang; Newcomb; Crich; Greenberg; Journal of the American Chemical Society; vol. 123; nb. 16; (2001); p.

3623 - 3629 View in Reaxys

45 %

2 : 4.2 General procedure for dihydroxylation of olefins General procedure: 0.006 mmol of l-selenocystine (3) and 2.39 mmol of H2O2 30 wt percent were stirred in water (1 mL) at room temperature for 10 min and 0.6 mmol of substrate were subsequently added. The reaction was monitored by TLC and by GCMS and after the time reported in Table 2 the aqueous mixture was extracted (three times) with EtOAc. The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude mixture was purified by flash chromatography on a silica gel column using a mixture of MeOH/EtOAc (2:98) as eluant. The structures of the products and the relative yields are reported in Table 2.

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1-Phenyl-1,2-propanediol [C9H12O2]

With seleno-L-cystine, water, dihydrogen peroxide, Time= 168h, T= 20 °C , Optical yield = 32 percent de; stereoselective reaction Santi, Claudio; Di Lorenzo, Rosalia; Tidei, Caterina; Bagnoli, Luana; Wirth, Thomas; Tetrahedron; vol. 68; nb. 51; (2012); p. 10530 - 10535,6 View in Reaxys With AD-mix-β, methanesulfonamide, potassium carbonate, potassium hexacyanoferrate(III), OsO4 immobilized on Amberlite XAD-4 in water, tert-butyl alcohol, Time= 1.5h, T= 20 °C Yang, Jung Woons; Han, Hogyu; Roh, Eun Joo; Lee, Sang-Gi; Song, Choong Eui; Organic Letters; vol. 4; nb. 26; (2002); p.

4685 - 4688 View in Reaxys With dihydrogen peroxide, nitric acid, potassium iodide in water, acetonitrile, Time= 4h, T= 24.84 °C , p= 760.051Torr , pH= Ca. 4 Saikia; Rajesh; Srinivas; Ratnasamy; Catalysis Letters; vol. 137; nb. 3-4; (2010); p. 190 - 201 View in Reaxys O

HO

O

HO Si

Rx-ID: 30359197 View in Reaxys 10/52 Yield

Conditions & References Reaction Steps: 2 1: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 20 h / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere With lithium aluminium tetrahydride, chloro(triphenylphosphine)gold(I), F5Sb*AgF, water in tetrahydrofuran, 1,4-dioxane Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys

O

HO O

HO O

Rx-ID: 30359377 View in Reaxys 11/52 Yield

Conditions & References Stage 1: With lithium aluminium tetrahydride in tetrahydrofuran, T= 0 °C , Inert atmosphere Stage 2: With hydrogenchloride in tetrahydrofuran, water Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys

HO

HO O O

Rx-ID: 30359386 View in Reaxys 12/52 Yield

Conditions & References Reaction Steps: 2

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1-Phenyl-1,2-propanediol [C9H12O2]

1: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere With lithium aluminium tetrahydride, chloro(triphenylphosphine)gold(I), F5Sb*AgF, water in tetrahydrofuran, 1,4-dioxane Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys OH

HO

HO Si

Rx-ID: 30359420 View in Reaxys 13/52 Yield

Conditions & References Reaction Steps: 3 1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere 2: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 20 h / 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere With dmap, lithium aluminium tetrahydride, chloro(triphenylphosphine)gold(I), F5Sb*AgF, water, triethylamine in tetrahydrofuran, 1,4-dioxane, dichloromethane Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys Reaction Steps: 4 1: methanol; potassium carbonate / 12 h / 20 °C / Inert atmosphere 2: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 3: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere With methanol, dmap, lithium aluminium tetrahydride, chloro(triphenylphosphine)gold(I), F5Sb*AgF, water, potassium carbonate, triethylamine in tetrahydrofuran, 1,4-dioxane, dichloromethane Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys OH

HO

H

HO

Rx-ID: 30359424 View in Reaxys 14/52 Yield

Conditions & References Reaction Steps: 3 1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere With dmap, lithium aluminium tetrahydride, chloro(triphenylphosphine)gold(I), F5Sb*AgF, water, triethylamine in tetrahydrofuran, 1,4-dioxane, dichloromethane Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys HO

H

HO O

Rx-ID: 30359474 View in Reaxys 15/52

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1-Phenyl-1,2-propanediol [C9H12O2]

Yield

Conditions & References Reaction Steps: 4 1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 1.2: 1.5 h / -70 - 20 °C / Inert atmosphere 1.3: 0 °C 2.1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere 3.1: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 20 h / 20 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere With dmap, lithium aluminium tetrahydride, n-butyllithium, chloro(triphenylphosphine)gold(I), F5Sb*AgF, water, triethylamine in tetrahydrofuran, 1,4-dioxane, dichloromethane Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys Reaction Steps: 5 1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere 1.2: 1.5 h / -70 - 20 °C / Inert atmosphere 1.3: 0 °C 2.1: methanol; potassium carbonate / 12 h / 20 °C / Inert atmosphere 3.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 4.1: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere With methanol, dmap, lithium aluminium tetrahydride, n-butyllithium, chloro(triphenylphosphine)gold(I), F5Sb*AgF, water, potassium carbonate, triethylamine in tetrahydrofuran, 1,4-dioxane, dichloromethane Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K.; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 500 - 511 View in Reaxys

O

O

O

HO

HO

HO

HO

O HO

H

O

Rx-ID: 31817637 View in Reaxys 16/52 Yield

Conditions & References With hydrogen in cyclohexane, p= 30003Torr , Kinetics, Time, optical yield given as percent ee, enantioselective reaction Campos, Cristian H.; Oportus, Marcelo; Torres, Cecilia; Urbina, Claudia; Fierro, Jose L.G.; Reyes, Patricio; Journal of Molecular Catalysis A: Chemical; vol. 348; nb. 1-2; (2011); p. 30 - 41 View in Reaxys

HO

Si O

Si O

HO

Rx-ID: 29124184 View in Reaxys 17/52 Yield

Conditions & References With tetrabutyl ammonium fluoride in tetrahydrofuran, Inert atmosphere, Cooling

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1-Phenyl-1,2-propanediol [C9H12O2]

Skjel, Miranda K.; Houghton, Adrian Y.; Kirby, Andrea E.; Harrison, Daniel J.; McDonald, Robert; Rosenberg, Lisa; Organic Letters; vol. 12; nb. 2; (2010); p. 376 - 379 View in Reaxys

HO

Si

O HO

O

Si

Rx-ID: 29124187 View in Reaxys 18/52 Yield

Conditions & References With tetrabutyl ammonium fluoride in tetrahydrofuran, Inert atmosphere, Cooling Skjel, Miranda K.; Houghton, Adrian Y.; Kirby, Andrea E.; Harrison, Daniel J.; McDonald, Robert; Rosenberg, Lisa; Organic Letters; vol. 12; nb. 2; (2010); p. 376 - 379 View in Reaxys O

HO O

HO

HO

Rx-ID: 29807684 View in Reaxys 19/52 Yield

Conditions & References

12 With 2-Picolinic acid, manganese(II) perchlorate hexahydrate, dihydrogen peroxide, sodium acetate, 1,2-dichloro-benzene in %Spectr., 7 water, acetone, T= 0 - 20 °C %Spectr., 65 %Spectr. Saisaha, Pattama; Pijper, Dirk; Van Summeren, Ruben P.; Hoen, Rob; Smit, Christian; De Boer, Johannes W.; Hage, Ronald; Alsters, Paul L.; Feringa, Ben L.; Browne, Wesley R.; Organic and Biomolecular Chemistry; vol. 8; nb. 19; (2010); p. 4444 - 4450 View in Reaxys

HO O

O B

O

HO B

O

Rx-ID: 28772109 View in Reaxys 20/52 Yield

Conditions & References With dihydrogen peroxide, sodium hydroxide in tetrahydrofuran, water, Time= 2h, T= 25 °C , Inert atmosphere Penno, Dirk; Lillo, Vanesa; Koshevoy, Igor O.; Sanau, Mercedes; Ubeda, M. Angeles; Lahuerta, Pascual; Fernandez, Elena; Chemistry - A European Journal; vol. 14; nb. 34; (2008); p. 10648 - 10655 View in Reaxys

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1-Phenyl-1,2-propanediol [C9H12O2]

HO

O

O

O

HO

O

Rx-ID: 10328945 View in Reaxys 21/52 Yield

Conditions & References

34 %, 66 %

With Amberlyst 15, Time= 12h, T= 20 °C Solladie-Cavallo, Ariette; Choucair, Elias; Balaz, Milan; Lupattelli, Paolo; Bonini, Carlo; Di Blasio, Nadia; European Journal of Organic Chemistry; nb. 13; (2006); p. 3007 - 3011 View in Reaxys

O

O

HO

HO

HO

O

HO

Rx-ID: 10070514 View in Reaxys 22/52 Yield

Conditions & References

6 %, 79 %, 3 %, 7 %

With samarium diiodide, water in tetrahydrofuran, Time= 0.166667h, T= 20 °C , Further byproducts given Kamochi, Yasuko; Kudo, Tadahiro; Masuda, Toshinobu; Takadate, Akira; Chemical and Pharmaceutical Bulletin; vol. 53; nb. 8; (2005); p. 1017 - 1020 View in Reaxys HO

HO

Rx-ID: 7248849 View in Reaxys 23/52 Yield 71 %

Conditions & References 7 Conversion of starting material Patent; Bayer Aktiengesellschaft; US6825377; (2004); (B1) English View in Reaxys Colonge et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 259; (1964); p. 3566 View in Reaxys Marshall; Prager; Australian Journal of Chemistry; vol. 30; (1977); p. 141,144. 150 View in Reaxys Chan et al.; Tetrahedron Letters; (1976); p. 2667,2669 View in Reaxys Ohnishi; Kagami; Tetrahedron Letters; (1975); p. 2437 View in Reaxys Zalesskaja; Lavrova; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 454,441 View in Reaxys Audier et al.; Bulletin de la Societe Chimique de France; (1968); p. 3844 View in Reaxys Representative preferred compounds include, but are not limited to: ...

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1-Phenyl-1,2-propanediol [C9H12O2]

(S)-(+)-1,2-Propanediol[(S)-(+)-1,2-Propylene Glycol] 1,3-Propanediol 2,3-Dimethyl-2,3-Butanediol 2,3-Dimethyl-1,2-Butanediol 1-Phenyl-1,2-Propanediol 2-Methyl-1,3-Propanediol 1,2-Butanediol 1,3-Butanediol ...

Patent; BROWN, DAVID A.; KHORLIN, ALEXANDER A.; LESIAK, KRYSTYNA; REN, WU YUN; US2002/141952; (2002); (A1) English View in Reaxys Representative preferred compounds include, but are not limited to: ...

(S)-(+)-1,2-Propanediol [(S)-(+)-1,2-Propylene Glycol] 1,3-Propanediol 2,3-Dimethyl-2,3-Butanediol 2,3-Dimethyl-1,2-Butanediol 1-Phenyl-1,2-Propanediol 2-Methyl-1,3-Propanediol 1,2-Butanediol 1,3-Butanediol ...

Patent; Codon Pharmaceuticals, Inc.; US5990177; (1999); (A) English View in Reaxys Representative preferred compounds include, but are not limited to: ...

(S)-(+)-1,2-Propanediol [(S)-(+)-1,2-Propylene Glycol] 1,3-Propanediol 2,3-Dimethyl-2,3-Butanediol 2,3-Dimethyl-1,2-Butanediol 1-Phenyl-1,2-Propanediol 2-Methyl-1,3-Propanediol 1,2-Butanediol 1,3-Butanediol 1,4-Butanediol 2,3-Butanediol (2R,3R)-(-)-2,3-Butanediol ...

Patent; Applied Genetics Incorporated Dermatics; US6110975; (2000); (A) English View in Reaxys OH HO

H Br

HO

O

Rx-ID: 9661739 View in Reaxys 24/52 Yield 17 %, 77 %

Conditions & References With bis(cyclopentadienyl)titanium (III) chloride in tetrahydrofuran, Time= 1.5h, T= 20 °C Jana, Samaresh; Guin, Chandrani; Roy, Subhas Chandra; Tetrahedron Letters; vol. 45; nb. 35; (2004); p. 6575 - 6577 View in Reaxys

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1-Phenyl-1,2-propanediol [C9H12O2]

O

O

HO O

O

O

O

HO

O

HO

Rx-ID: 8941993 View in Reaxys 25/52 Yield

Conditions & References

42 %

With ammonium sulfate, D-glucose, Rhizopus oryzae NRRL 395, magnesium sulfate, zinc(II) sulfate in phosphate buffer, dimethyl sulfoxide, Time= 60h, T= 30 °C , pH= 6.0 - 6.5 Demir, Ayhan S.; Hamamci, Haluk; Sesenoglu, Ozge; Aydogan, Feray; Capanoglu, Doga; Neslihanoglu, Rahsan; Tetrahedron Asymmetry; vol. 12; nb. 13; (2001); p. 1953 - 1956 View in Reaxys HO O

HO

Rx-ID: 10289377 View in Reaxys 26/52 Yield

Conditions & References

34 % Spectr., 43 % Spectr.

With Oxone, (S)-diphenylmethilpyrrolidine, sodium hydrogencarbonate in [D3]acetonitrile, water-d2, Time= 2h, T= 20 °C , Epoxidation Adamo, Mauro F. A.; Aggarwal, Varinder K.; Sage, Matthew A.; Journal of the American Chemical Society; vol. 122; nb.

34; (2000); p. 8317 - 8318 View in Reaxys HO

HO

H

OH

HO O

OH

Rx-ID: 5206841 View in Reaxys 27/52 Yield 51 %, 49 %

Conditions & References Time= 3h, T= 20 °C , pinacol coupling Ji, Shun-Jun; Matsushita, Masatoshi; Takahashi, T. Tomoyoshi; Horiuchi, C. Akira; Tetrahedron Letters; vol. 40; nb. 37; (1999); p. 6791 - 6794 View in Reaxys O

HO H

HO

HO O

Rx-ID: 4986221 View in Reaxys 28/52 Yield

Conditions & References With laccase from Trametes versicolor, oxygen, benzotriazol-1-ol in water, T= 45 °C , pH=4.5 Fritz-Langhals, Elke; Kunath, Brigitte; Tetrahedron Letters; vol. 39; nb. 33; (1998); p. 5955 - 5956 View in Reaxys HO

H

<(Me2C)2O2B>CH(CH3)ZnI

HO

O

Rx-ID: 7248851 View in Reaxys 29/52

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1-Phenyl-1,2-propanediol [C9H12O2]

Yield

Conditions & References With boron trifluoride diethyl etherate, dihydrogen peroxide, sodium acetate, ammonium chloride, Yield given. Multistep reaction Sakai, Masaaki; Saito, Syunn; Kanai, Gen; Suzuki, Akira; Miyaura, Norio; Tetrahedron; vol. 52; nb. 3; (1996); p. 915 - 924 View in Reaxys HO

O

HO

Rx-ID: 3821293 View in Reaxys 30/52 Yield

Conditions & References With water, enantioselectivity and regioselectivity by cytosolic and microsomal epoxide hydrolase, Product distribution Bellucci, Giuseppe; Chiappe, Cinzia; Cordoni, Antonio; Marioni, Franco; Tetrahedron Letters; vol. 35; nb. 24; (1994); p.

4219 - 4222 View in Reaxys HO

O

HO

Rx-ID: 3821296 View in Reaxys 31/52 Yield

Conditions & References With water, enantioselectivity and regioselectivity by cytosolic and microsomal epoxide hydrolase, Product distribution Bellucci, Giuseppe; Chiappe, Cinzia; Cordoni, Antonio; Marioni, Franco; Tetrahedron Letters; vol. 35; nb. 24; (1994); p.

4219 - 4222 View in Reaxys

HO

O Si

HO

O

Rx-ID: 3999237 View in Reaxys 32/52 Yield

Conditions & References

90 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 1h, Heating Vries, Erik F. J. de; Brussee, Johannes; Gen, Arne van der; Journal of Organic Chemistry; vol. 59; nb. 23; (1994); p. 7133 7137 View in Reaxys

HO

O

O

HO

O

HO

Rx-ID: 3840941 View in Reaxys 33/52 Yield

Conditions & References bioreduction with baker's yeast; pH effect, Product distribution Chenevert, Robert; Thiboutot, Sonia; Chemistry Letters; (1988); p. 1191 - 1192 View in Reaxys

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1-Phenyl-1,2-propanediol [C9H12O2]

O

O

HO

HO

HO HO

HO

Rx-ID: 3840953 View in Reaxys 34/52 Yield

Conditions & References With lithium aluminium tetrahydride, oxygen, T= 110 °C , p= 759.8Torr , 1.) oxidation, 2.) reductiv reactions of different βdiketones to different products, Product distribution Rao, T. S. S.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 3; (1987); p. 474 - 482 View in Reaxys O

HO

HO

HO

Rx-ID: 2063277 View in Reaxys 35/52 Yield

Conditions & References With sodium tetrahydroborate Ohta, Hiromichi; Ozaki, Kazuhiko; Konishi, Jin; Tsuchihashi, Gen-ichi; Agricultural and Biological Chemistry; vol. 50; nb.

5; (1986); p. 1261 - 1266 View in Reaxys OH

HO

HO

SiH

O

HO

Rx-ID: 2539760 View in Reaxys 36/52 Yield

Conditions & References With dihydrogen peroxide, sodium hydrogencarbonate, dihydrogen hexachloroplatinate, Yield given. Multistep reaction. Yields of byproduct given Tamao, Kohei; Tanaka, Tetsu; Nakajima, Takashi; Sumiya, Ritsuo; Arai, Hitoshi; Ito, Yoshihiko; Tetrahedron Letters; vol.

27; nb. 29; (1986); p. 3377 - 3380 View in Reaxys HO

Br

copper bromide

HO

Rx-ID: 18510915 View in Reaxys 37/52 Yield

Conditions & References Reaction Steps: 3 1: tetrahydrofuran 2: 76 percent / morpholine / tetrahydrofuran / 3 h / Ambient temperature 3: sodiuk borohydride With morpholine, sodium tetrahydroborate in tetrahydrofuran Ohta, Hiromichi; Ozaki, Kazuhiko; Konishi, Jin; Tsuchihashi, Gen-ichi; Agricultural and Biological Chemistry; vol. 50; nb.

5; (1986); p. 1261 - 1266 View in Reaxys

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1-Phenyl-1,2-propanediol [C9H12O2]

HO

Br–

+Mg

etheric (+-)-ethyl-<1.2-dibromo-ethyl>-ether

HO

Rx-ID: 18525528 View in Reaxys 38/52 Yield

Conditions & References Reaction Steps: 2 1: 76 percent / morpholine / tetrahydrofuran / 3 h / Ambient temperature 2: sodiuk borohydride With morpholine, sodium tetrahydroborate in tetrahydrofuran Ohta, Hiromichi; Ozaki, Kazuhiko; Konishi, Jin; Tsuchihashi, Gen-ichi; Agricultural and Biological Chemistry; vol. 50; nb.

5; (1986); p. 1261 - 1266 View in Reaxys HO

HO

HO

Rx-ID: 21402910 View in Reaxys 39/52 Yield

Conditions & References Reaction Steps: 2 2: 2.) 30percent H2O2, NaHCO3 / 1.) H2PtCl6*6H2O With dihydrogen peroxide, sodium hydrogencarbonate, dihydrogen hexachloroplatinate Tamao, Kohei; Tanaka, Tetsu; Nakajima, Takashi; Sumiya, Ritsuo; Arai, Hitoshi; Ito, Yoshihiko; Tetrahedron Letters; vol.

27; nb. 29; (1986); p. 3377 - 3380 View in Reaxys HO

HO

H

O

O

O

O

HO

O

Rx-ID: 1764003 View in Reaxys 40/52 Yield

Conditions & References

3.4 %, 26.9 %, 3.2 %, 2.9 %, 0.8 %, 55.1 %

With 2,2'-azobis(isobutyronitrile), oxygen in chlorobenzene, T= 120 °C , p= 759.8Torr , Product distribution, Mechanism Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys HO

H

HO

O

O

O

O

O

HO

Rx-ID: 1764007 View in Reaxys 41/52 Yield 2.7 %, 26.4 %, 2.9 %,

Conditions & References With 2,2'-azobis(isobutyronitrile), oxygen in chlorobenzene, T= 100 °C , p= 759.8Torr , Product distribution, Mechanism

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1-Phenyl-1,2-propanediol [C9H12O2]

3.2 %, 52.1 %, 0.4 %

Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys HO

HO

O

O

O

H

O

O

HO

Rx-ID: 2005268 View in Reaxys 42/52 Yield

Conditions & References

2.2 %, 24.5 %, 1.8 %, 4.0 %, 7.4 %, 32.4 %

With 2,2'-azobis(isobutyronitrile), oxygen in chlorobenzene, T= 120 °C , p= 759.8Torr , Product distribution, Mechanism Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys HO

HO

H

O

O

HO

O

O

O

Rx-ID: 2005273 View in Reaxys 43/52 Yield

Conditions & References

2.1 %, 38.7 %, 6.3 %, 3.5 %, 33.1 %, 1.8 %

With 2,2'-azobis(isobutyronitrile), oxygen, chlorobenzene, T= 80 °C , p= 759.8Torr , other temperature, Product distribution, Mechanism Fuchs, K. P.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 322; nb. 3; (1980); p. 353 - 361 View in Reaxys

O HO

Cl

Cl

HO

Rx-ID: 1073061 View in Reaxys 44/52 Yield

Conditions & References With sodium hydroxide, nickel Bratchanskii,P.E.; Komissarova,G.G.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 1661 - 1665,1650 - 1654 View in Reaxys HO

methylbenzoylcarbinol

HO

Rx-ID: 7248852 View in Reaxys 45/52 Yield

Conditions & References durch Einw. von gaerender Hefe (Linksdrehende Praeparate, in denen wahrscheinlich Gemische von Stereoisomeren vorliegen) Neuberg; Komarewsky; Biochemische Zeitschrift; vol. 182; (1927); p. 287

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1-Phenyl-1,2-propanediol [C9H12O2]

View in Reaxys v. Falkenhausen; Biochemische Zeitschrift; vol. 219; (1930); p. 242,247 View in Reaxys Einw. gaerender Hefe (inakt. Methylphenylaethylenglykol) Kotschergin; Bulletin de la Societe Chimique de France; vol. <4> 43; (1928); p. 575 View in Reaxys Faworski; Kotschergin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 60; (1928); p. 399 View in Reaxys HO

Cl

H

HO

O

Rx-ID: 5487580 View in Reaxys 46/52 Yield

Conditions & References T= 20 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 60; (1927); p. 1062; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 204 View in Reaxys HO

Br –O

O

O

OH

K+

Br

HO

Rx-ID: 639814 View in Reaxys 47/52 Yield

Conditions & References Verseifen des Reaktionsgemisches mit alkoh. Kalilauge Zincke; Zahn; Chemische Berichte; vol. 43; (1910); p. 855 View in Reaxys HO

Br H

H O

Br

K2CO3

HO

Rx-ID: 7248853 View in Reaxys 48/52 Yield

Conditions & References Zincke; Zahn; Chemische Berichte; vol. 43; (1910); p. 855 View in Reaxys

HO O

O

Mg

I HO HO

O

Rx-ID: 665096 View in Reaxys 49/52 Yield

Conditions & References With diethyl ether, Zersetzung des Reaktionsprodukts mit Wasser und Essigsaeure Stoermer; Chemische Berichte; vol. 39; (1906); p. 2297 View in Reaxys Reagiert analog mit Aethylmagnesiumjodid Stoermer; Chemische Berichte; vol. 39; (1906); p. 2297 View in Reaxys

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1-Phenyl-1,2-propanediol [C9H12O2]

Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 1261; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 342 View in Reaxys HO HO

Brâ&#x20AC;&#x201C;

HO

+Mg

Cl

HO

OH OH

Rx-ID: 745654 View in Reaxys 50/52 Yield

Conditions & References Patent; Grignard; DE164883 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 45; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 30; Chem. Zentralbl.; vol. 76; nb. II; (1905); p. 1751 View in Reaxys O

HO O

Mg

O

I HO

Rx-ID: 93300 View in Reaxys 51/52 Yield

Conditions & References Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 137; (1903); p. 1261; Annales de Chimie (Cachan, France); vol. <8> 10; (1907); p. 342 View in Reaxys HO

11.12-dibromo-1-propyl-benzene

HO

Rx-ID: 7248850 View in Reaxys 52/52 Yield

Conditions & References With potassium acetate, acetic acid, man verseift die erhaltene Acetylverbindung mit alkoh. Kalilauge, low-melting form Zincke; Chemische Berichte; vol. 17; (1884); p. 709 View in Reaxys With potassium carbonate, high-melting form Zincke; Chemische Berichte; vol. 17; (1884); p. 709 View in Reaxys

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