(2S,3R)-3-Cyclohexylmethyl-2-ethoxy-2-trifluoromethyl-oxirane | 141937-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-Cyclohexylmethyl-2-ethoxy-2-trifluoromethyl-oxirane
• 英文别名: (2S,3R)-3-(cyclohexylmethyl)-2-ethoxy-2-(trifluoromethyl)oxirane
• CAS: 141937-90-8
• 化学式: C₁₂H₁₉F₃O₂
• 分子量: 252.277
• InChiKey: HOPVNFUJWHTLGL-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Cyclohexylmethyl-2-ethoxy-2-trifluoromethyl-oxirane 在 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以50%的产率得到bromo-3 trifluoro-1,1,1 cyclohexyl-4 butanone-2
  参考文献：
  名称：

  A New and Efficient Synthesis of α-Bromoalkyl Perfluoroalkyl Ketones via Opening of Epoxides

  摘要：

  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。

  DOI：

  10.1055/s-1993-26004
• 作为产物：
  描述：

  (Z)-ethyl 1-trifluoromethyl-3-cyclohexyl-1-propenyl ether 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2S,3R)-3-Cyclohexylmethyl-2-ethoxy-2-trifluoromethyl-oxirane
  参考文献：
  名称：

  A New and Efficient Synthesis of α-Bromoalkyl Perfluoroalkyl Ketones via Opening of Epoxides

  摘要：

  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。

  DOI：

  10.1055/s-1993-26004

文献信息

• Synthesis of 3-(Alkylthio and Phenylthio)-1,1,1-trifluoroalkan-2-ones via Ring Opening of Epoxy Ethers
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Andrei Kornilov

  DOI：10.1055/s-1996-4235

  日期：1996.4

  Regioselective ring opening of 1-trifluoromethyl epoxy ethers 2 was achieved with alkyl and phenyl sodium thiolates to afford new 3-(alkylthio and phenylthio)-1,1,1-trifluoroalkan-2-ones 3-5 in good yields.

  1-三氟甲基环氧乙烷2的选择性开环反应通过烷基和苯基硫醇钠实现，以良好产率得到了新型3-(烷硫基和苯硫基)-1,1,1-三氟代烷-2-酮3-5。
• 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。
• Stereoselective and Enantioselective Synthesis of <i>anti</i>-1-(Trifluoromethyl) Amino Alcohols
  作者：Ahmed Abouabdellah、Jean-Pierre Bégué、Danièle Bonnet-Delpon、Andrei Kornilov、Isabelle Rodrigues、Cyrille Richard

  DOI：10.1021/jo9805448

  日期：1998.9.1

  anti-(Trifluoromethyl) beta-amino alcohols 2 have been prepared in good yields and with 90% diastereoisomeric excess through a reaction of 1-(trifluoromethyl) epoxy ethers 3 with dimethylaluminum amide, followed by the in situ chelation-controlled stereoselective reduction of the intermediate amino ketone. The salen-mediated chiral epoxidation of 1-(trifluoromethyl) enol ether 4a led to the homochiral epoxy ethers 11a and 12a in a good enantiomeric excess. Reaction with dimethylaluminum amide followed by a reduction step provided the chiral amino alcohols 15a and 16a, respectively.
• Stereoselective synthesis and inhibitor properties towards human leucocyte elastase of chiral β-peptidyl trifluoromethyl alcohols.
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Nathalie Fischer-Durand、Augustin Amour、Michèle Reboud-Ravaux

  DOI：10.1016/0957-4166(94)80061-8

  日期：1994.6

  The synthesis of chiral peptidyl trifluoromethyl alcohols 9 and 10 was performed from easily available epoxy ethers 3, through different stereocontrol of the reduction of the azido ketone 4. One stereoisomer in each pair of the diastereoisomeric peptidyl trifluoromethyl alcohols 9 and 10 behaved as reversible inhibitors of human leucocyte elastase, a serine protease implicated in inflammatory related diseases.
• Fluorinated Synthons: Reactivity of 1-RF-Epoxy Ethers with Lewis Acids
  作者：Jean-Pierre Begue、Farid Benayoud、Daniele Bonnet-Delpon

  DOI：10.1021/jo00121a023

  日期：1995.8

  Fluorinated epoxy ethers 2, 5, 6, and 12 react with Lewis acids to give different ring opening products, depending upon the structure and the experimental conditions. Both nucleophile-assisted and stepwise processes can occur. In all cases, except when a phenyl group stabilizes the C beta secondary carbenium ion, the C alpha-O bond is broken leading to addition, transposition, or cyclization products. EtAlCl(2) reacted with epoxy ethers 2a-c providing chlorohydrins 3a and the transposed products 4b,c and 5b,c. With epoxy ethers 6a-c aldehydes 7a-c were formed through a transposition. Epoxy ethers 9a-c underwent ring opening to the chloroketones 10a-c with EtAlCl(2) and TiCl4 and 9a gave the glycol ether 11a with Me(3)Al. Epoxy ether 12a was transformed into a mixture of chlorohydrin 13a(1) (S*R*) and the cyclized product 14a (S*R*) with TiCl4 or EtAlCl(2) at -78 degrees C. At room temperature, the cyclized products 14a (S*R*) or 15c were selectively obtained in good yields from 12a and 12c, respectively, with TiCl4.