vinyl 3-[4-(trifluoromethyl)phenyl]propanoate | 351014-62-5

• 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: vinyl 3-[4-(trifluoromethyl)phenyl]propanoate
• 英文别名: vinyl 3-(4-trifluoromethylphenyl)propanoate；Ethenyl 3-[4-(trifluoromethyl)phenyl]propanoate
• CAS: 351014-62-5
• 化学式: C₁₂H₁₁F₃O₂
• 分子量: 244.213
• InChiKey: DGAAADRVJRYANN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-methylphenyl)-6-hepten-1-ol 、 vinyl 3-[4-(trifluoromethyl)phenyl]propanoate 在 Lipase PS 作用下， 以 正己烷 为溶剂， 反应 24.5h， 以76%的产率得到(S)-2-(4-methylphenyl)-6-hepten-1-yl 3-(4-trifluoromethylphenyl)propanoate
  参考文献：
  名称：

  使用脂肪酶催化3-（4-三氟甲基苯基）丙酸乙烯酯对伯醇的高对映选择性酯交换反应，不对称合成5,6-脱氢二烯数字烯

  摘要：

  通过脂肪酶催化的3-（4-三氟甲基苯基）丙酸乙烯基酯的外消旋伯醇的高度对映选择性动力学拆分，得到对映体纯的伯醇。该方法的多功能性在5,6-脱氢亚烯二烯（R）-1的不对称合成中得到了证明。

  DOI：

  10.1016/j.tetasy.2005.10.041
• 作为产物：
  描述：

  乙酸乙烯酯 、 3-(4-三氟甲基苯基)丙酸 在 palladium diacetate 作用下， 以82%的产率得到vinyl 3-[4-(trifluoromethyl)phenyl]propanoate
  参考文献：
  名称：

  The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols

  摘要：

  The enantioselectivity of the lipase from Pseudomonas cepacia (PCL) in the transesterification of 2-phenyl-1-propanol I was studied using a series of vinyl 3-arylpropanoates as acyl donors. The most enantioselective transesterification reaction of the alcohol was attained by using vinyl 3-(p-iodophenyl)- or 3-(p-trifluoromethylphenyl)propanoates, with enantiomer ratios, E, of 116 and 138, respectively. Vinyl 3-phenylpropanoate was also effective for the resolution of 1 mediated by lipases from P. fluorescens and porcine pancreas and for the PCL-catalysed transesterification of several 2-phenyl-1-alkanols. The enantiomeric resolution of 1 was practically carried out by the first enantioselective transesterification using PCL and vinyl 3-(p-iodophenyl)propanoate to afford (R)-1 and then the enantioselective hydrolysis of the resultant ester to afford (S)-1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00083-0

文献信息

• Dynamic Kinetic Resolution of Primary Alcohols with an Unfunctionalized Stereogenic Center in the β-Position
  作者：Dirk Strübing、Patrik Krumlinde、Julio Piera、Jan-E. Bäckvall

  DOI：10.1002/adsc.200700222

  日期：2007.7.2

  Primary alcohols with an unfunctionalized stereogenic center in the β-position undergo an enzyme- and metal-catalyzed dynamic kinetic resolution (DKR). The in situ racemization of the primary alcohol, required for the DKR, takes place via: (i) ruthenium-catalyzed dehydrogenation of the alcohol, (ii) enolization of the aldehyde formed, and (iii) ruthenium-catalyzed readdition of hydrogen to the aldehyde

  在β位置具有未官能化立体生成中心的伯醇会经历酶和金属催化的动态动力学拆分（DKR）。在原位的伯醇，对于DKR需要的外消旋化，发生通过：（ⅰ）钌催化脱氢的醇，（II）所形成的醛烯醇化，和（iii）钌催化readdition氢与醛。本方法拓宽了金属和酶催化的DKR的范围，迄今为止，该方法仅限于α-手性醇和胺衍生物。
• The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols
  作者：Masashi Kawasaki、Michimasa Goto、Shigeki Kawabata、Tadashi Kometani

  DOI：10.1016/s0957-4166(01)00083-0

  日期：2001.3

  The enantioselectivity of the lipase from Pseudomonas cepacia (PCL) in the transesterification of 2-phenyl-1-propanol I was studied using a series of vinyl 3-arylpropanoates as acyl donors. The most enantioselective transesterification reaction of the alcohol was attained by using vinyl 3-(p-iodophenyl)- or 3-(p-trifluoromethylphenyl)propanoates, with enantiomer ratios, E, of 116 and 138, respectively. Vinyl 3-phenylpropanoate was also effective for the resolution of 1 mediated by lipases from P. fluorescens and porcine pancreas and for the PCL-catalysed transesterification of several 2-phenyl-1-alkanols. The enantiomeric resolution of 1 was practically carried out by the first enantioselective transesterification using PCL and vinyl 3-(p-iodophenyl)propanoate to afford (R)-1 and then the enantioselective hydrolysis of the resultant ester to afford (S)-1. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of 5,6-dehydrosenedigitalene using lipase-catalyzed highly enantioselective transesterification of a primary alcohol with vinyl 3-(4-trifluoromethylphenyl)propanoate
  作者：Masashi Kawasaki、Yuko Hayashi、Hiroko Kakuda、Naoki Toyooka、Akira Tanaka、Michimasa Goto、Shigeki Kawabata、Tadashi Kometani

  DOI：10.1016/j.tetasy.2005.10.041

  日期：2005.12

  The highly enantioselective kinetic resolution of a racemic primary alcohol by lipase-catalyzed transesterification with vinyl 3-(4-trifluoromethylphenyl)propanoate afforded an enantiomerically pure primary alcohol. The versatility of this approach is shown in the asymmetric synthesis of 5,6-dehydrosenedigitalene (R)-1.

  通过脂肪酶催化的3-（4-三氟甲基苯基）丙酸乙烯基酯的外消旋伯醇的高度对映选择性动力学拆分，得到对映体纯的伯醇。该方法的多功能性在5,6-脱氢亚烯二烯（R）-1的不对称合成中得到了证明。