(Z)-2,2,2-trifluoro-1-(furan-2-yl)ethanone O-benzyloxime | 413599-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2,2,2-trifluoro-1-(furan-2-yl)ethanone O-benzyloxime
• 英文别名: (Z)-2,2,2-trifluoro-1-(furan-2-yl)-N-phenylmethoxyethanimine
• CAS: 413599-92-5
• 化学式: C₁₃H₁₀F₃NO₂
• 分子量: 269.223
• InChiKey: SAPQTFHTMYDRBB-ATVHPVEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-2,2,2-trifluoro-1-(furan-2-yl)ethanone O-benzyloxime 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以88%的产率得到2,2,2-三氟-1-(呋喃-2-基)乙胺
  参考文献：
  名称：

  An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-1-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-1-furan-2-yl-ethanone

  摘要：

  The selective conversion of 2,2,2-trifluoro-1-furan-2-yl-ethanone into (E)- and (Z)-oximes and oxime ethers and subsequent oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2-yl-ethylamine with e.e. of up to 88%. Oxidation of the furan ring afforded both enantiomers of 3,3,3-trifluoroalanine in 91-93% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00410-4
• 作为产物：
  描述：

  2,2,2-三氟-1-呋喃-2-乙酮 在 盐酸羟胺 、 sodium acetate 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (Z)-2,2,2-trifluoro-1-(furan-2-yl)ethanone O-benzyloxime
  参考文献：
  名称：

  An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-1-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-1-furan-2-yl-ethanone

  摘要：

  The selective conversion of 2,2,2-trifluoro-1-furan-2-yl-ethanone into (E)- and (Z)-oximes and oxime ethers and subsequent oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2-yl-ethylamine with e.e. of up to 88%. Oxidation of the furan ring afforded both enantiomers of 3,3,3-trifluoroalanine in 91-93% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00410-4

文献信息

• An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-1-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-1-furan-2-yl-ethanone
  作者：Ayhan S. Demir、Özge Sesenoglu、Zuhal Gerçek-Arkin

  DOI：10.1016/s0957-4166(01)00410-4

  日期：2001.9

  The selective conversion of 2,2,2-trifluoro-1-furan-2-yl-ethanone into (E)- and (Z)-oximes and oxime ethers and subsequent oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2-yl-ethylamine with e.e. of up to 88%. Oxidation of the furan ring afforded both enantiomers of 3,3,3-trifluoroalanine in 91-93% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.