Ethyl E-3-F-heptyl 2-propenoate | 37759-80-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl E-3-F-heptyl 2-propenoate
• 英文别名: 2-(Perfluorheptyl)ethylacrylat；2H,3H-pentadecafluoro-dec-2t-enoic acid ethyl ester；2H,3H-Pentadecafluor-dec-2t-ensaeure-aethylester；ethyl (E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluorodec-2-enoate
• CAS: 37759-80-1
• 化学式: C₁₂H₇F₁₅O₂
• 分子量: 468.162
• InChiKey: ZYANAGKZDBNVOF-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  Ethyl E-3-F-heptyl 2-propenoate 在 lithium aluminium tetrahydride 作用下， 生成 ((1S,2S,3S,4R)-3-Pentadecafluoroheptyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol
  参考文献：
  名称：

  Stereochemistry of the Diels-Alder reaction. V. Fluorinated trans-olefinic acids and derivatives with cyclopentadiene

  摘要：

  DOI：

  10.1021/jo00944a002
• 作为产物：
  描述：

  2H,2H,3H-pentadecafluoro-3-hydroxy-decanoic acid 在 盐酸 、 phosphorus pentoxide 作用下， 生成 Ethyl E-3-F-heptyl 2-propenoate
  参考文献：
  名称：

  Perfluoroalkyl-substituted Dicarboxylic Acids and Derivatives^1,2

  摘要：

  DOI：

  10.1021/ja01566a082

文献信息

• Stereoselective synthesis of F-alkyl α,β-unsaturated esters and their epoxidation
  作者：Marion Lanier、Mustapha Haddach、Raphael Pastor、Jean G. Riess

  DOI：10.1016/s0040-4039(00)60443-4

  日期：1993.4

  Strong electrophilic Z and E 3-F-alkyl 2-propenoates have been prepared stereoselectively. Their extremely difficult epoxidation has been achieved with retention of stereohemistry using t-BuO2Li, leading to F-alkyl glycidic esters, which are useful building blocks for the synthesis of new amphiphiles.

  已经立体选择性地制备了强亲电的Z和E 3- F-烷基2-丙酸酯。通过使用t-BuO 2 Li保留立体异构，已经实现了其极其困难的环氧化作用，从而导致F-烷基缩水甘油酯，这是合成新两亲物的有用组成部分。
• <b>Stereochemistry of the Diels-Alder Reaction. III. Fluorinated <b><i>trans</i></b>-Olefinic Acids as Dienophiles</b>
  作者：H. P. Braendlin、A. Z. Zielinski、E. T. McBee

  DOI：10.1021/ja00870a022

  日期：1962.6
• Stereoselective synthesis of Z and E 3-F-alkyl 2-propenoates and derivatives
  作者：Marion Lanier、Raphaël Pastor

  DOI：10.1016/0022-1139(95)03297-q

  日期：1995.11

  The stereoselective preparation of 3-F-alkyl 2-propenoates and their derivatives is described. E-isomers are easily obtained by an in situ reduction-olefination from esters of F-acids and phosphonates or by a convenient dehydration of 3-F-alkyl 3-hydroxyesters. Z-isomers an known to be prepared by the hydrogenation of alkynes.
• McBee et al., Journal of the American Chemical Society
  作者：McBee et al.

  DOI：——

  日期：——
• Perfluoroalkyl-substituted Dicarboxylic Acids and Derivatives^1,2
  作者：E. T. McBee、C. W. Roberts、Gordon Wilson

  DOI：10.1021/ja01566a082

  日期：1957.5