(Z)-ethyl 1-trifluoromethyl-3-cyclohexyl-1-propenyl ether | 136430-46-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: (Z)-ethyl 1-trifluoromethyl-3-cyclohexyl-1-propenyl ether
• 英文别名: (Z)-1,1,1-trifluoro-4-cyclohexyl-2-ethoxy-2-butene；[(Z)-3-ethoxy-4,4,4-trifluorobut-2-enyl]cyclohexane
• CAS: 136430-46-1
• 化学式: C₁₂H₁₉F₃O
• 分子量: 236.277
• InChiKey: QEKNKLHOLDRWFT-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 1-trifluoromethyl-3-cyclohexyl-1-propenyl ether 在 硫酸 作用下， 以 甲醇 为溶剂， 生成 4-cyclohexyl-1,1,1-trifluorobutan-2-one
  参考文献：
  名称：

  Begue, Jean-Pierre; Benayoud, Farid; Bonnet-Delpon, Daniele, Gazzetta Chimica Italiana, 1995, vol. 125, # 9, p. 399 - 402

  摘要：

  DOI：
• 作为产物：
  描述：

  三氟乙酸乙酯 、 (2-Cyclohexyl-ethyl)-triphenyl-phosphonium 在 sodium amide 、 六甲基二硅氮烷 作用下， 生成 (Z)-ethyl 1-trifluoromethyl-3-cyclohexyl-1-propenyl ether
  参考文献：
  名称：

  The Wittig reaction of perfluoro acid derivatives: access to fluorinated enol ethers, enamines, and ketones

  摘要：

  The preparation of novel perfluoroalkyl-substituted compounds in good yields is described. This preparation involves the Wittig reaction of a phosphonium ylide with perfluoroalkyl acid derivatives. The influence of the structure of the starting alkylidenetriphenylphosphoranes, the perfluoroalkyl reagents, and the reaction conditions has been investigated. Trifluoroacetamides lead to a Z/E mixture of enamines 3. Perfluoroalkyl esters (Rf = CF3, C2F5, C3F7, C7F15, CF2Cl) lead to only the (Z)-enol ethers 8-12 when reactions are performed with NaNH2 as a base and to 1-perfluoroalkyl ketones 13-17 when reactions are performed with BuLi.

  DOI：

  10.1021/jo00040a017

文献信息

• A New and Efficient Synthesis of α-Bromoalkyl Perfluoroalkyl Ketones via Opening of Epoxides
  作者：Farid Benayoud、Jean-Pierre Bégué、Danièle Bonnet-Delpon、Nathalie Fischer-Durand、Hamid Sdassi

  DOI：10.1055/s-1993-26004

  日期：——

  Regioselective ring opening of various substituted perfluoroepoxy ethers was achieved with magnesium bromide, leading to new α-bromofluoroalkyl ketones in good yields.

  使用溴化镁实现了各种取代的全氟环氧醚的区域选择性开环反应，获得了良好产率的新型α-溴氟烷基酮。
• A versatile synthesis of amino trifluoromethyl ketones and Alcohols
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Hamid Sdassi

  DOI：10.1016/s0040-4039(00)74166-9

  日期：1992.3

  A short, selective and general route to α-amino trifluoromethyl ketones and corresponding alcohols is described via an easy epoxidation of 1-CF3 enol ethers followed by an opening with various secondary amines.

  通过1-CF 3烯醇醚的容易的环氧化，然后用各种仲胺进行开环，描述了制备α-氨基三氟甲基酮和相应的醇的短的，选择性的和一般的途径。
• The Wittig reaction of perfluoro acid derivatives: access to fluorinated enol ethers, enamines, and ketones
  作者：Jean Pierre Begue、Daniele Bonnet-Delpon、Dany Mesureur、Gerard Nee、Sheng Wen Wu

  DOI：10.1021/jo00040a017

  日期：1992.7

  The preparation of novel perfluoroalkyl-substituted compounds in good yields is described. This preparation involves the Wittig reaction of a phosphonium ylide with perfluoroalkyl acid derivatives. The influence of the structure of the starting alkylidenetriphenylphosphoranes, the perfluoroalkyl reagents, and the reaction conditions has been investigated. Trifluoroacetamides lead to a Z/E mixture of enamines 3. Perfluoroalkyl esters (Rf = CF3, C2F5, C3F7, C7F15, CF2Cl) lead to only the (Z)-enol ethers 8-12 when reactions are performed with NaNH2 as a base and to 1-perfluoroalkyl ketones 13-17 when reactions are performed with BuLi.
• Begue, Jean-Pierre; Benayoud, Farid; Bonnet-Delpon, Daniele, Gazzetta Chimica Italiana, 1995, vol. 125, # 9, p. 399 - 402
  作者：Begue, Jean-Pierre、Benayoud, Farid、Bonnet-Delpon, Daniele、Allen, Annette D.、Cox, Robin A.、Tidwell, Thomas T.

  DOI：——

  日期：——