vinyl-para-methoxycinnamate | 10604-64-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: vinyl-para-methoxycinnamate
• 英文别名: 4-methoxy-trans-cinnamic acid vinyl ester；4-Methoxy-trans-zimtsaeure-vinylester；ethenyl (E)-3-(4-methoxyphenyl)prop-2-enoate
• CAS: 10604-64-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: NTSSZLIMHGXZHV-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-ethylhexan-1-ol 、 vinyl-para-methoxycinnamate 以 正己烷 为溶剂， 反应 20.0h， 生成 S-(+)-2-ethylhexyl-para-methoxycinnamate
  参考文献：
  名称：

  Preparation of S-2-Ethylhexyl-para-methoxycinnamate by lipase catalyzed sequential kinetic resolution

  摘要：

  S-2-Ethylhexyl-para-methoxycinnamate S-6 is prepared by a sequential biocatalytic resolution. First, either enantioselective acetylation of rac 2-ethylhexanol (+/-)-1 by vinylacetate to R-(-)-2-ethylhexylacetate R-2, or alcoholysis of rac 2-ethylhexylbutyrate (+/-)-3 by n-butanol to S-(+)-2-ethylhexanol S-1 is completed, than, without isolation of the enantiomerically enreached S-alcohol, its enantioselective acylation with the activated para-methoxycinnammic acid derivatives 4,5 is performed, both steps being catalyzed by different microbial lipases. The highest amplification of enantioselectivity is obtained by combining acetylation of rac 2-ethylhexanol catalyzed by Penicillium camembertii lipase or alcoholysis of rac 2-ethylhexylbutyrate catalyzed by Pseudomonas species lipase in the first step, with acylation of enantiomerically enriched S-1 by vinyl-para-methoxycinnamate 4 catalyzed by Lipozyme IM lipase; 84.5% e.e. of S-6 is achieved in the first, and 88% e.e. in the second approach. Since the R-enantiomer of 2-ethylhexanol represents potential source of teratogenic R-2-ethylhexanoic acid, S-6 is regarded as biologicaly safer UV filter as compared to racemic 2-ethylhexyl-para-methoxycinnamate. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00078-x
• 作为产物：
  描述：

  乙酸乙烯酯 、 反式-4-甲氧基肉桂酸 在 硫酸 作用下， 反应 1.5h， 以69%的产率得到vinyl-para-methoxycinnamate
  参考文献：
  名称：

  Preparation of S-2-Ethylhexyl-para-methoxycinnamate by lipase catalyzed sequential kinetic resolution

  摘要：

  S-2-Ethylhexyl-para-methoxycinnamate S-6 is prepared by a sequential biocatalytic resolution. First, either enantioselective acetylation of rac 2-ethylhexanol (+/-)-1 by vinylacetate to R-(-)-2-ethylhexylacetate R-2, or alcoholysis of rac 2-ethylhexylbutyrate (+/-)-3 by n-butanol to S-(+)-2-ethylhexanol S-1 is completed, than, without isolation of the enantiomerically enreached S-alcohol, its enantioselective acylation with the activated para-methoxycinnammic acid derivatives 4,5 is performed, both steps being catalyzed by different microbial lipases. The highest amplification of enantioselectivity is obtained by combining acetylation of rac 2-ethylhexanol catalyzed by Penicillium camembertii lipase or alcoholysis of rac 2-ethylhexylbutyrate catalyzed by Pseudomonas species lipase in the first step, with acylation of enantiomerically enriched S-1 by vinyl-para-methoxycinnamate 4 catalyzed by Lipozyme IM lipase; 84.5% e.e. of S-6 is achieved in the first, and 88% e.e. in the second approach. Since the R-enantiomer of 2-ethylhexanol represents potential source of teratogenic R-2-ethylhexanoic acid, S-6 is regarded as biologicaly safer UV filter as compared to racemic 2-ethylhexyl-para-methoxycinnamate. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00078-x

文献信息

• Method for esterification of polyvinyl alcohol-based resin, resultant modified polyvinyl alcohol-based resin, and method for production of the same
  申请人：Nitta Daisuke

  公开号：US20090247698A1

  公开（公告）日：2009-10-01

  A gist of the present invention lies in a method for esterification of a polyvinyl alcohol-based resin, wherein a vinyl ester is used as an esterifying agent in a method for esterification of a polyvinyl alcohol-based resin by an esterification reaction using an esterifying agent. The esterification method can esterify the polyvinyl alcohol-based resin at a high reaction rate under mild reaction conditions using relatively simple reaction equipment, and is also applicable to a wide variety of polyvinyl alcohol-based resins without being restricted by polymerization and saponification degrees of the polyvinyl alcohol-based resin. Thus, it is possible to provide a modified polyvinyl alcohol-based resin having excellent physical properties such as polymerization and modification degrees, which is applicable to various applications.
• US5538823A
  申请人：——

  公开号：US5538823A

  公开（公告）日：1996-07-23
• US5705096A
  申请人：——

  公开号：US5705096A

  公开（公告）日：1998-01-06
• Preparation of S-2-Ethylhexyl-para-methoxycinnamate by lipase catalyzed sequential kinetic resolution
  作者：Maja Majerié、Vitomir Šunjié

  DOI：10.1016/0957-4166(96)00078-x

  日期：1996.3

  S-2-Ethylhexyl-para-methoxycinnamate S-6 is prepared by a sequential biocatalytic resolution. First, either enantioselective acetylation of rac 2-ethylhexanol (+/-)-1 by vinylacetate to R-(-)-2-ethylhexylacetate R-2, or alcoholysis of rac 2-ethylhexylbutyrate (+/-)-3 by n-butanol to S-(+)-2-ethylhexanol S-1 is completed, than, without isolation of the enantiomerically enreached S-alcohol, its enantioselective acylation with the activated para-methoxycinnammic acid derivatives 4,5 is performed, both steps being catalyzed by different microbial lipases. The highest amplification of enantioselectivity is obtained by combining acetylation of rac 2-ethylhexanol catalyzed by Penicillium camembertii lipase or alcoholysis of rac 2-ethylhexylbutyrate catalyzed by Pseudomonas species lipase in the first step, with acylation of enantiomerically enriched S-1 by vinyl-para-methoxycinnamate 4 catalyzed by Lipozyme IM lipase; 84.5% e.e. of S-6 is achieved in the first, and 88% e.e. in the second approach. Since the R-enantiomer of 2-ethylhexanol represents potential source of teratogenic R-2-ethylhexanoic acid, S-6 is regarded as biologicaly safer UV filter as compared to racemic 2-ethylhexyl-para-methoxycinnamate. (C) 1996 Elsevier Science Ltd