2-(Perfluorooctyl)cyclohexanone | 146560-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Perfluorooctyl)cyclohexanone
• 英文别名: 2-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluorooctyl)cyclohexan-1-one
• CAS: 146560-62-5
• 化学式: C₁₄H₉F₁₇O
• 分子量: 516.198
• InChiKey: ZISCJUDXJLSFTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2-(Perfluorooctyl)cyclohexanone 在 盐酸羟胺 、 potassium carbonate 作用下， 生成 3,4-(1',4'-Butylene)-5-pentadecafluoroheptylisoxazole
  参考文献：
  名称：

  Synthesis of per(poly)fluoroalkylisoxazoles

  摘要：

  4,5-(1',4'-Butylene)-3-per(poly) fluoroalkylisoxazoles 2 are synthesized by the reaction of the alpha-per(poly) fluoroalkyl cyclohexanones 1 with hydroxylamine hydrochloride in the presence of potassium carbonate under reflux in ethanol. The isomeric 3,4-(1',4'-butylene)-5-per (poly) fluoroalkylisoxazoles 3 can be prepared by a reaction of 1, first with hydroxylamine hydrochloride to give the corresponding oximes 4, followed by the treatment of the resultant reaction mixture with potassium carbonate in a one-pot procedure.

  DOI：

  10.1016/0022-1139(95)03248-c
• 作为产物：
  描述：

  十七氟辛烷亚磺酸钠 、 环己烯 在 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以70%的产率得到2-(Perfluorooctyl)cyclohexanone
  参考文献：
  名称：

  α-（全氟烷基）酮的新型合成

  摘要：

  在紫外线辐射和氧气气氛下，全卤代氟烷基亚磺酸钠与烯烃的反应以良好的收率提供了α-全卤代氟烷基酮。

  DOI：

  10.1016/s0022-1139(00)80336-x

文献信息

• Tang, Xiao-Qing; Hu, Chang-Ming, Journal of the Chemical Society. Perkin transactions I, 1995, # 8, p. 1039 - 1044
  作者：Tang, Xiao-Qing、Hu, Chang-Ming

  DOI：——

  日期：——
• New Method for Trifluoromethylation of Enolate Anions and Applications to Regio-, Diastereo- and Enantioselective Trifluoromethylation
  作者：Teruo Umemoto、Kenji Adachi

  DOI：10.1021/jo00098a030

  日期：1994.9

  Assessment was made of the effectiveness of different boron Lewis acids in mediating the trifluoromethylation of reactive enolate anions with S- and Se-(trifluoromethyl)chalcogen salts. Treatment of potassium or lithium enolates derived in situ from carbonyl compounds or enol trimethylsilyl ethers with S-(trifluoromethyl)dibenzothiophenium triflate (1) in the presence of 2-phenyl-1,3,2-benzodioxaborole (4) produced trifluoromethylated carbonyl compounds in high yields. Iq this manner, various alpha-CF3 ketones, gamma-CF3-alpha,beta-unsaturated ketones, and an alpha-CF3 ester were synthesized. Perfluorooctylation was similarly conducted using S-(perfluorooctyl)dibenzothiophenium triflate and 4. Thus, a balance of the reactivity of the reactants was essential for these electrophilic perfluoroalkylations. The deprotonation of 2-methylcyclohexanone with KN(SiMe(3))(2) followed by trifluoromethylation gave the 6-trifluoromethylated product regioselectively. In the trifluoromethylation of potassium enolate 16 of 4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone, the use of bulky 2-mesitylphenanthro[9,10-d]-1,3,2-dioxaborole (15) led to the diastereo-selective formation of the thermodynamically less stable CF3-isomer 17 beta. For enantioselective trifluoromethylation, optically active (S)-4-phenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaborepin(19) and its 3,3'-diphenyl derivative 20 were synthesized. The trifluoromethylation of the potassium enolate of propiophenone with 1 in the presence of 20 afforded optically active alpha-CF3-propiophenone in 45% ee yield. Thus, a new and versatile method for selective trifluoromethylation has been developed.
• A novel synthesis of α-(perfluoroalkyl) ketones
  作者：Chang-Ming Hu、Xiao-Qing Tang、Feng-Ling Qing

  DOI：10.1016/s0022-1139(00)80336-x

  日期：1992.12

  Reaction of sodium perhalofluoroalkyl sulfinates with alkenes under UV irradiation and oxygen atmosphere provides α-perhalofluoroalkyl ketones in good yields.

  在紫外线辐射和氧气气氛下，全卤代氟烷基亚磺酸钠与烯烃的反应以良好的收率提供了α-全卤代氟烷基酮。
• Synthesis of per(poly)fluoroalkylisoxazoles
  作者：Xiao-Qing Tang、Chang-Ming Hu

  DOI：10.1016/0022-1139(95)03248-c

  日期：1995.9

  4,5-(1',4'-Butylene)-3-per(poly) fluoroalkylisoxazoles 2 are synthesized by the reaction of the alpha-per(poly) fluoroalkyl cyclohexanones 1 with hydroxylamine hydrochloride in the presence of potassium carbonate under reflux in ethanol. The isomeric 3,4-(1',4'-butylene)-5-per (poly) fluoroalkylisoxazoles 3 can be prepared by a reaction of 1, first with hydroxylamine hydrochloride to give the corresponding oximes 4, followed by the treatment of the resultant reaction mixture with potassium carbonate in a one-pot procedure.