二环己基甲酮

二环己基甲酮
英文名	Dicyclohexylmethanone; Dicyclohexyl ketone
识别
CAS号	119-60-8
EINECS	204-336-0
性质
化学式	C13H22O
摩尔质量	194.31 g·mol⁻¹
密度	0.986 g/mL
熔点	61 °C
沸点	138 °C (13 mmHg); 159 °C (20 Torr)
折光度n; D	1.486 (589.3 nm, 20 °C)
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

二环己基甲酮是一种有机化合物，化学式为C₁₃H₂₂O，该化合物可看作丙酮的甲基替换为环己基。二环己基甲酮可燃，其燃烧产物为碳氧化物。^[5]

合成

二环己基甲酮可以由环己酰氯和环己基溴化镁反应得到。^[6]环己腈和格氏试剂的反应也能得到二环己基甲酮。^[7]

性质

二环己基甲酮的羰基可以和三乙基硅烷在二氯甲烷中反应，在一种苯并喹啉茂基铱催化剂的存在下，生成(C₆H₁₁)₂CH-O-Si(C₂H₅)₃。^[8]它也可以和苯肼盐酸盐在乙酸中回流，制得含氮杂环化合物：^[9]

它在铁催化剂（如乙酰丙酮铁）的存在下可以被三乙基硼氢化钠还原为相应的醇。^[10]以锂粉-萘-无水氯化镍作为还原体系，在四氢呋喃溶剂中对其进行还原，在室温下便可得到相应的醇。^[11]

甲基溴化镁与其作用得到的是1,1-二环己基乙醇。^[12]

二环己基甲酮在5~10 °C和三溴化磷进行溴化反应，得到二溴代产物二(1-溴环己基)甲酮。^[13]

参考文献

^ ^1.0 ^1.1 二环己基甲酮 (119-60-8) CAS数据库. Chemical Book. [2018-7-16]
^ Venus-Danilova, E. D.; Transformation of asymmetric dicyclohexylethylene oxide J. Russ. Phys.-Chem. Soc. 1929, 61, pp 1479-1484 CAPLUS
^ Mousseron, Max; Granger, Robert. Alicyclic series. VI. The organomagnesium compounds. Bulletin de la Societe Chimique de France 1946, pp 251-256 CAPLUS
^ Smushkevich, Yu. I.; Belov, V. N.; Kleev, B. V.; Golger, A. Ya. Reaction of aldehydes with olefins. I. Reaction of aldehydes with cyclohexene. Zhurnal Obshchei Khimii. 1964, V34(11), P3815-17 CAPLUS
^ 二环己基甲酮化学品安全技术说明书. SigmaAldrich. [2018-7-16]
^ Mousseron, Max; Granger, Robert. Alicyclic series. VI. The organomagnesium compounds. Bulletin de la Societe Chimique de France. 1946. 251-256.
^ Canonne, Persephone; Foscolos, George B.; Lemay, Gilles. Effet du benzene dans la reaction de Grignard sur les nitriles（法文）. Tetrahedron Letters, 1980. 21 (2): 155-158. doi:10.1016/S0040-4039(00)71400-6
^ Hamdaoui, Mustapha; Desrousseaux, Camille; Habbita, Houda; Djukic, Jean-Pierre. Iridacycles as Catalysts for the Autotandem Conversion of Nitriles into Amines by Hydrosilylation: Experimental Investigation and Scope. Organometallics, 2017. 36 (24): 4864-4882. doi:10.1021/acs.organomet.7b00749
^ Bakulina, Olga; Ivanov, Alexander; Suslonov, Vitalii; Dar'in, Dmitry; Krasavin, Mikhail. A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline. Beilstein Journal of Organic Chemistry, 2017 (13): 1413-1424. doi:10.3762/bjoc.13.138
^ Tamang, Sem Raj; Findlater, Michael. Iron Catalyzed Hydroboration of Aldehydes and Ketones. Journal of Organic Chemistry, 2017. 82 (23): 12857-12862. doi:10.1021/acs.joc.7b02020
^ Alonso, Francisco; Candela, Pablo; Gomez, Cecilia; Yus, Miguel. The NiCl2-Li-arene (cat.) combination as reducing system, part 9: Catalytic hydrogenation of organic compounds using the NiCl2-Li-(naphthalene or polymer-supported naphthalene) (cat.) combination. Advanced Synthesis & Catalysis. 2003, 345 (1+2): 275-279. doi:10.1002/adsc.200390022.
^ Son, Eun-Kyung; Kang, Jae-Hyun; Kim, Deog-Bae; Kim, Jae-Hyun. Chemically amplified polymer having pendant group with dicyclohexyl for photoresist composition. PCT Int. Appl., 2004. WO 2004042477.
^ Montana, Angel M.; Barcia, Joan A.; Grima, Pedro M.; Kociok-Kohn, Gabriele. New methodology for the synthesis of tetrahydrofuro[3,2-b]furan-2(3H)-one derivatives, synthons of natural products with biological interest. Tetrahedron, 2016. 72 (43). 6794-6806. doi:10.1016/j.tet.2016.09.004

[ChemicalBook-1] 1.0 ^1.1 二环己基甲酮 (119-60-8) CAS数据库. Chemical Book. [2018-7-16]

[2] Venus-Danilova, E. D.; Transformation of asymmetric dicyclohexylethylene oxide J. Russ. Phys.-Chem. Soc. 1929, 61, pp 1479-1484 CAPLUS

[3] Mousseron, Max; Granger, Robert. Alicyclic series. VI. The organomagnesium compounds. Bulletin de la Societe Chimique de France 1946, pp 251-256 CAPLUS

[4] Smushkevich, Yu. I.; Belov, V. N.; Kleev, B. V.; Golger, A. Ya. Reaction of aldehydes with olefins. I. Reaction of aldehydes with cyclohexene. Zhurnal Obshchei Khimii. 1964, V34(11), P3815-17 CAPLUS

[5] 二环己基甲酮化学品安全技术说明书. SigmaAldrich. [2018-7-16]

[6] Mousseron, Max; Granger, Robert. Alicyclic series. VI. The organomagnesium compounds. Bulletin de la Societe Chimique de France. 1946. 251-256.

[7] Canonne, Persephone; Foscolos, George B.; Lemay, Gilles. Effet du benzene dans la reaction de Grignard sur les nitriles（法文）. Tetrahedron Letters, 1980. 21 (2): 155-158. doi:10.1016/S0040-4039(00)71400-6

[8] Hamdaoui, Mustapha; Desrousseaux, Camille; Habbita, Houda; Djukic, Jean-Pierre. Iridacycles as Catalysts for the Autotandem Conversion of Nitriles into Amines by Hydrosilylation: Experimental Investigation and Scope. Organometallics, 2017. 36 (24): 4864-4882. doi:10.1021/acs.organomet.7b00749

[9] Bakulina, Olga; Ivanov, Alexander; Suslonov, Vitalii; Dar'in, Dmitry; Krasavin, Mikhail. A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline. Beilstein Journal of Organic Chemistry, 2017 (13): 1413-1424. doi:10.3762/bjoc.13.138

[10] Tamang, Sem Raj; Findlater, Michael. Iron Catalyzed Hydroboration of Aldehydes and Ketones. Journal of Organic Chemistry, 2017. 82 (23): 12857-12862. doi:10.1021/acs.joc.7b02020

[11] Alonso, Francisco; Candela, Pablo; Gomez, Cecilia; Yus, Miguel. The NiCl2-Li-arene (cat.) combination as reducing system, part 9: Catalytic hydrogenation of organic compounds using the NiCl2-Li-(naphthalene or polymer-supported naphthalene) (cat.) combination. Advanced Synthesis & Catalysis. 2003, 345 (1+2): 275-279. doi:10.1002/adsc.200390022.

[12] Son, Eun-Kyung; Kang, Jae-Hyun; Kim, Deog-Bae; Kim, Jae-Hyun. Chemically amplified polymer having pendant group with dicyclohexyl for photoresist composition. PCT Int. Appl., 2004. WO 2004042477.

[13] Montana, Angel M.; Barcia, Joan A.; Grima, Pedro M.; Kociok-Kohn, Gabriele. New methodology for the synthesis of tetrahydrofuro[3,2-b]furan-2(3H)-one derivatives, synthons of natural products with biological interest. Tetrahedron, 2016. 72 (43). 6794-6806. doi:10.1016/j.tet.2016.09.004

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