2-(Diphenylmethyl)cyclohexanone [C19H20O]

2-(Diphenylmethyl)cyclohexanone [C19H20O]

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17 reactions in Reaxys

2018-08-02 12h:29m:38s (UTC)

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='30614-39-2') AND (IDE.INCHI='QWIDEBUXIADHDYUHFFFAOYSA-N') NOT (RX.RXRN=1984300))

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2-(Diphenylmethyl)cyclohexanone [C19H20O]

Cl O

O

Si Si Cl

Rx-ID: 45194138 View in Reaxys 1/17 Yield

Conditions & References With carbon dioxide, Time= 20h, T= 70 °C , p= 142514Torr , Inert atmosphere, Autoclave, Supercritical conditions Qiao, Yun X.; Theyssen, Nils; Eifert, Tobias; Liauw, Marcel A.; Franciò, Giancarlo; Schenk, Karolin; Leitner, Walter; Reetz, Manfred T.; Chemistry - A European Journal; vol. 23; nb. 16; (2017); p. 3898 - 3902 View in Reaxys OH O Si

O

Si

O

O

Rx-ID: 45334468 View in Reaxys 2/17 Yield 15 %Spectr., 8 %Spectr., 72 %

Conditions & References General procedure for the scope of silicon enolates (mechanical slow-injection method) General procedure: In a 30 mL round-bottomed flask was placed 20 mg of Sn-Mont. Sn-Mont was activated under vacuum at 120 oC for 1 h. Then, into the flask was added 0.9 mL of chlorobenzene and the suspended mixture was heated at 120 oC. Into the mixture was added a solution of 1.0 mmol of the alcohol 2a and 2.0 mmol of the silicon enolates in 1.1 mL of chlorobenzene dropwise with a syringe pump for 15 min. After the addition was completed, the mixture was further heated at 120 oC for 15 min. The mixture was then cooled to room temperature. The solid catalyst was filtered off, and the filtrate was concentrated and applied to NMR analysis. The desired alkylated product was isolated through the purification of the concentrated mixture by silica-gel column chromatography.

With tin hydroxide-embedded montmorillonite in chlorobenzene, Time= 0.5h, T= 120 °C Tandiary, Michael Andreas; Asano, Masashi; Hattori, Taiki; Takehira, Satoshi; Masui, Yoichi; Onaka, Makoto; Tetrahedron Letters; vol. 58; nb. 20; (2017); p. 1925 - 1928 View in Reaxys OH

O Si

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2-(Diphenylmethyl)cyclohexanone [C19H20O]

O Si O

Rx-ID: 45334472 View in Reaxys 3/17 Yield

Conditions & References

82 %Spectr., 9 %Spectr.

General procedure for the scope of silicon enolates (mechanical slow-injection method) General procedure: In a 30 mL round-bottomed flask was placed 20 mg of Sn-Mont. Sn-Mont was activated under vacuum at 120 oC for 1 h. Then, into the flask was added 0.9 mL of chlorobenzene and the suspended mixture was heated at 120 oC. Into the mixture was added a solution of 1.0 mmol of the alcohol 2a and 2.0 mmol of the silicon enolates in 1.1 mL of chlorobenzene dropwise with a syringe pump for 15 min. After the addition was completed, the mixture was further heated at 120 oC for 15 min. The mixture was then cooled to room temperature. The solid catalyst was filtered off, and the filtrate was concentrated and applied to NMR analysis. The desired alkylated product was isolated through the purification of the concentrated mixture by silica-gel column chromatography.

With tin hydroxide-embedded montmorillonite in chlorobenzene, Time= 0.5h, T= 120 °C Tandiary, Michael Andreas; Asano, Masashi; Hattori, Taiki; Takehira, Satoshi; Masui, Yoichi; Onaka, Makoto; Tetrahedron Letters; vol. 58; nb. 20; (2017); p. 1925 - 1928 View in Reaxys

O

O

Rx-ID: 45334489 View in Reaxys 4/17 Yield

Conditions & References Reaction Steps: 2 1: triethylamine; sodium iodide / acetonitrile; hexane / 20 °C / Inert atmosphere 2: tin hydroxide-embedded montmorillonite / chlorobenzene / 0.5 h / 120 °C With triethylamine, sodium iodide in hexane, chlorobenzene, acetonitrile Tandiary, Michael Andreas; Asano, Masashi; Hattori, Taiki; Takehira, Satoshi; Masui, Yoichi; Onaka, Makoto; Tetrahedron Letters; vol. 58; nb. 20; (2017); p. 1925 - 1928 View in Reaxys

O

O

Si Cl

Si O

Rx-ID: 45334490 View in Reaxys 5/17 Yield

Conditions & References Reaction Steps: 2 1: triethylamine; sodium iodide / acetonitrile; hexane / 20 °C / Inert atmosphere 2: tin hydroxide-embedded montmorillonite / chlorobenzene / 0.5 h / 120 °C With triethylamine, sodium iodide in hexane, chlorobenzene, acetonitrile

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2-(Diphenylmethyl)cyclohexanone [C19H20O]

Tandiary, Michael Andreas; Asano, Masashi; Hattori, Taiki; Takehira, Satoshi; Masui, Yoichi; Onaka, Makoto; Tetrahedron Letters; vol. 58; nb. 20; (2017); p. 1925 - 1928 View in Reaxys

O

OH

Si

O

Rx-ID: 40294651 View in Reaxys 6/17 Yield 42 %

Conditions & References With 3-dodecyl-2-iodo-1-methyl-1H-imidazol-3-ium hexafluoroantimonate, iodine in nitromethane, Time= 2h, T= 20 °C , Inert atmosphere Saito, Masato; Tsuji, Nobuya; Kobayashi, Yusuke; Takemoto, Yoshiji; Organic Letters; vol. 17; nb. 12; (2015); p. 3000 3003 View in Reaxys

O

OH

O

O HO

Rx-ID: 41447502 View in Reaxys 7/17 Yield 88 %

Conditions & References With iodine in nitromethane, Time= 2h, T= 70 °C , Schlenk technique Han, Fuzhong; Zhang, Xinxin; Hu, Minggang; Jia, Lina; Organic and Biomolecular Chemistry; vol. 13; nb. 47; (2015); p.

11466 - 11471 View in Reaxys

OH

O

O

Rx-ID: 34138206 View in Reaxys 8/17 Yield 75 %

Conditions & References With aluminium(III) triflate in nitromethane, Time= 1h, T= 80 °C , Microwave irradiation Ohshima, Takashi; Ipposhi, Junji; Nakahara, Yasuhito; Shibuya, Ryozo; Mashima, Kazushi; Advanced Synthesis and Catalysis; vol. 354; nb. 13; (2012); p. 2447 - 2452 View in Reaxys

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2-(Diphenylmethyl)cyclohexanone [C19H20O]

O

O

O HO NH O

S O

Rx-ID: 31390639 View in Reaxys 9/17 Yield

Conditions & References

56 %

With iron(III) chloride in 1,2-dichloro-ethane, Time= 2h, T= 60 °C , regioselective reaction Yang, Cui-Feng; Wang, Jian-Yong; Tian, Shi-Kai; Chemical Communications; vol. 47; nb. 29; (2011); p. 8343 - 8345 View in Reaxys

O

O

S

O

O

Rx-ID: 8786295 View in Reaxys 10/17 Yield 61 %

Conditions & References With tetraethylammonium perchlorate in N,N-dimethyl-formamide, T= 20 °C , Electrochemical reaction Ozaki; Yoshinaga; Matsui; Adachi; Journal of Organic Chemistry; vol. 66; nb. 7; (2001); p. 2503 - 2505 View in Reaxys

O

O

NaN3

Rx-ID: 15498314 View in Reaxys 11/17 Yield

Conditions & References Reaction Steps: 3 1.1: NaH / dimethylsulfoxide / 65 °C 1.2: 20 °C 2.1: 32 percent / DCC; DMAP / CH2Cl2 / 2 h / 20 °C 3.1: 61 percent / tetraethylammonium perchlorate / dimethylformamide / 20 °C / Electrochemical reaction With dmap, tetraethylammonium perchlorate, sodium hydride, dicyclohexyl-carbodiimide in dichloromethane, dimethyl sulfoxide, N,N-dimethyl-formamide Ozaki; Yoshinaga; Matsui; Adachi; Journal of Organic Chemistry; vol. 66; nb. 7; (2001); p. 2503 - 2505 View in Reaxys

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2-(Diphenylmethyl)cyclohexanone [C19H20O]

O

O OH

Rx-ID: 15504963 View in Reaxys 12/17 Yield

Conditions & References Reaction Steps: 2 1: 32 percent / DCC; DMAP / CH2Cl2 / 2 h / 20 °C 2: 61 percent / tetraethylammonium perchlorate / dimethylformamide / 20 °C / Electrochemical reaction With dmap, tetraethylammonium perchlorate, dicyclohexyl-carbodiimide in dichloromethane, N,N-dimethyl-formamide Ozaki; Yoshinaga; Matsui; Adachi; Journal of Organic Chemistry; vol. 66; nb. 7; (2001); p. 2503 - 2505 View in Reaxys

O

HO Br–

O P+

Rx-ID: 15509066 View in Reaxys 13/17 Yield

Conditions & References Reaction Steps: 3 1.1: NaH / dimethylsulfoxide / 65 °C 1.2: 20 °C 2.1: 32 percent / DCC; DMAP / CH2Cl2 / 2 h / 20 °C 3.1: 61 percent / tetraethylammonium perchlorate / dimethylformamide / 20 °C / Electrochemical reaction With dmap, tetraethylammonium perchlorate, sodium hydride, dicyclohexyl-carbodiimide in dichloromethane, dimethyl sulfoxide, N,N-dimethyl-formamide Ozaki; Yoshinaga; Matsui; Adachi; Journal of Organic Chemistry; vol. 66; nb. 7; (2001); p. 2503 - 2505 View in Reaxys

O

(2-methoxy-1,3-cyclohexadiene>Fe(CO3) complex

Rx-ID: 7207135 View in Reaxys 14/17 Yield

Conditions & References With n-butyllithium, trifluoroacetic acid, Yield given. Multistep reaction Hwu, Chong-Chen; Yeh, Ming-Chang P.; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 42; nb. 5; (1995); p.

825 - 832 View in Reaxys

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2-(Diphenylmethyl)cyclohexanone [C19H20O]

O

O Br–

+Mg

Rx-ID: 763542 View in Reaxys 15/17 Yield

Conditions & References With diethyl ether Freeman; Journal of the American Chemical Society; vol. 80; (1958); p. 1926,1929 View in Reaxys Miyano,K.; Taguchi,T.; Chemical and Pharmaceutical Bulletin; vol. 18; (1970); p. 1799 - 1805 View in Reaxys

O

Rx-ID: 7207134 View in Reaxys 16/17 Yield

Conditions & References Bicyclo<4.1.0>heptan IV, Ethylenglykol Bolesov,I.G. et al.; Zhurnal Organicheskoi Khimii; vol. 6; (1970); p. 2431 - 2434,2443 - 2445 View in Reaxys 1-Benzyliden-cyclohexanon-(2), PhMgBr, Ae. Winthrop; Humber; Journal of Organic Chemistry; vol. 26; (1961); p. 2834 View in Reaxys

O

O Br–

HO

+Mg

Rx-ID: 853778 View in Reaxys 17/17 Yield

Conditions & References With benzene Freeman; Journal of the American Chemical Society; vol. 80; (1958); p. 1926,1929 View in Reaxys

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