vinyl 3-(4-methylphenyl)propanoate | 240801-32-5

• 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-methylphenyl)propanoate
• 英文别名: vinyl 3-(p-tolyl)propanoate；Ethenyl 3-(4-methylphenyl)propanoate
• CAS: 240801-32-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: ZLQICRSMMMTNCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2-苯基-1-丙醇 、 vinyl 3-(4-methylphenyl)propanoate 在 lipase from Pseudomonas Cepacia 作用下， 以 环己烷 为溶剂， 反应 4.0h， 以20%的产率得到[(2S)-2-phenylpropyl] 3-(4-methylphenyl)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
• 作为产物：
  描述：

  diethyl 4-methylbenzylmalonate 在 palladium diacetate 、 sodium hydroxide 作用下， 以 乙醇 、 xylene 为溶剂， 反应 12.0h， 生成 vinyl 3-(4-methylphenyl)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

• Lipase-catalyzed transesterification of 2-phenyl-1-propanol with vinyl esters having aromatic ring in acyl moiety
  作者：Masashi Kawasaki、Michimasa Goto、Shigeki Kawabata、Tomoko Kodama、Tadashi Kometani

  DOI：10.1016/s0040-4039(99)00943-0

  日期：1999.7

  The highly enantioselective transesterification of 2-phenyl-1-propanol, which has not been efficiently resolved by lipase-catalyzed reactions, was attained by using either vinyl 3-(p-tolyl)propanoate or vinyl 3-(2-naphthyl)propanoate as the acyl donor. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Enzymatic kinetic resolution of 1-(3′-furyl)-3-buten-1-ol and 2-(2′-furyl)-propan-1-ol
  作者：Anja Bierstedt、Jörn Stölting、Roland Fröhlich、Peter Metz

  DOI：10.1016/s0957-4166(02)00023-x

  日期：2002.1

  The enzymatic kinetic resolution of the racemic alcohols 1-(3'-furyl)-3-buten-1-ol(+/-)-1 and 2-(2'-furyl)propan-1-ol (+/-)-2 was investigated by screening a range of lipases and esterases for enantioselective transacylation, as well as for enantioselective hydrolysis. For both alcohols, lipase-catalyzed hydrolysis of the derived racemic acetate gave the best results for accessing the desired (S)-enantiomers. In the case of the secondary alcohol (+/-)-1 ASL turned out to be the optimum enzyme, whereas PPL was found to be superior in the case of the primary alcohol (+/-)-2. Additionally, an alternative access to (S)-2 via Oppolzer's camphor sultam methodology is described. (C) 2002 Elsevier Science Ltd. All rights reserved.