(+/-)-vinyl 2-phenylpropanoate | 117760-33-5

• 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 2-phenylpropanoate
• 英文别名: Ethenyl 2-phenylpropanoate
• CAS: 117760-33-5
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: OXOOCPOAHFLTSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (+/-)-vinyl 2-phenylpropanoate 生成 (S)-(+)-2-phenylpropionic acid vinyl ester
  参考文献：
  名称：

  Highly efficient double enantioselection by lipase-catalyzed transesterification of (R,S)-carboxylic acid vinyl esters with (RS)-1-phenylethanol

  摘要：

  Transesterification of the title compounds using lipase B from Candida antarctica in toluene afforded the corresponding esters in good to excellent diastereomeric excess. (R)-2-Phenylpropionic acid-(R)-1-phenethyl ester 4 was isolated in 45% yield and 64% de after 2.5 h, whereas (R)-2-phenylbutyric acid-(R)-1-phenethyl ester 5 was obtained in 40% yield and 56% de after 35 h. A single recrystallization from n-hexane gave 4 with 98% de. In all reactions CAL-B showed excellent enantioselectivity (E > 100) toward (RS)-1-phenylethanol and moderate enantioselectivity (E similar to 10) toward both carboxylic acid vinyl esters. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00073-7
• 作为产物：
  描述：

  (S)-(+)-2-phenylpropionic acid vinyl ester 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 (+/-)-vinyl 2-phenylpropanoate
  参考文献：
  名称：

  酯的选择性外消旋作用：与酶促水解反应的相关性

  摘要：

  已经证明在相应的酸存在下酯的选择性外消旋化。苯基酯比甲基酯更易于外消旋化。初步结果表明这些结果在酶催化的水解反应中的实用性。

  DOI：

  10.1016/s0040-4039(98)02362-4

文献信息

• Dual Activity of Grubbs-Type Catalyst in the Transvinylation of Carboxylic Acids and Ring-Closing Metathesis Reactions
  作者：Anna Brodzka、Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1021/acs.joc.0c02135

  日期：2020.12.4

  This new activity of Grubbs catalysts was evidenced on several examples. It allows us to design a transvinylation/ring-closing metathesis (RCM) cascade reaction leading to the formation of endocyclic enol lactones from unsaturated carboxylic acids in an one-pot procedure. This unique ability of Grubbs catalyst to catalyze multiple mechanically distinct cascade reactions in a chemoselective way offers

  开发一种模仿酶的混杂性的多功能催化剂，可以在单个反应容器中催化多种化学转化，是现代可持续化学的关键点之一。我们的实验结果表明，格拉布斯型催化剂具有这种多任务活性，可以催化羧酸的乙烯基转移反应，而不会失去其原有的复分解活性。格拉布斯催化剂的这种新活性已在几个例子中得到证实。它使我们能够设计一种乙烯基转移/闭环复分解（RCM）级联反应，从而在一锅法中从不饱和羧酸形成环内烯醇内酯。格拉布斯催化剂以化学选择性方式催化多个机械上不同的级联反应的独特能力为从简单、易于获得的底物合成复杂化合物提供了新的可能性。
• Model Studies on the Enzyme‐Regulated Stereodivergent Cascade Passerini Reaction
  作者：Monika Wilk、Anna Brodzka、Dominik Koszelewski、Jan Samsonowicz‐Górski、Ryszard Ostaszewski

  DOI：10.1002/ejoc.202100760

  日期：2021.8.6

  An enzyme regulated-cascade reaction to form an important class of chiral compounds for medicinal chemistry with up to 99 % ee was designed and its feasibility proven.

  设计了一种酶调节级联反应，以形成一类重要的药物化学手性化合物，其ee高达 99% ，并证明了其可行性。
• Oxygen and carbon-acylation of enolates by ketenes
  作者：Lynn M. Bairgrie、Régis Leung-Toung、Thomas T. Tidwell

  DOI：10.1016/s0040-4039(00)82014-6

  日期：1988.1

  Ketenes react with lithium enolates mainly by O-acylation, thus providing a convenient route to vinyl esters and their enolates.

  酮基团主要通过O-酰化与烯醇化锂反应，从而为获得乙烯基酯及其烯醇化物提供了便利的途径。
• Heat-fixable electrophotographic toner
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0183566A2

  公开（公告）日：1986-06-04

  A heat-flexible electrophotographic toner composition comprising (A) a graft modified polyolefin composed of 100 parts by weight of a polyolefin having an intrinsic viscosity, measured in decalin at 135°C, of from 0.04 to 1.2 dl/g, and grafted thereto a monomer selected from the group consisting of (a) 1.0 to 100 parts by weight of acrylonitrile or methacrylonitrile, (b) 3 to 200 parts by weight of an aromatic carboxylic acid vinyl ester and (c) 2 to 43 parts by weight of an unsaturated carboxylic acid ester, and (B) a coloring agent.

  一种热柔性电子照相调色剂组合物，包括 (A) 一种接枝改性聚烯烃，由 100 重量份的聚烯烃组成，该聚烯烃在 135 摄氏度下以癸醛计的固有粘度为 0.04 至 1.2 分升/克，并接枝了选自以下组别的单体 (a) 1.0 至 100 份（按重量计）丙烯腈或甲基丙烯腈，(b) 3 至 200 份（按重量计）芳香族羧酸乙烯基酯，(c) 2 至 43 份（按重量计）不饱和羧酸酯。 (B) 着色剂。
• Adhesive for chlorine-containing polymers and aromatic group-containing polymers
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0181094A1

  公开（公告）日：1986-05-14

  Disclosed is a thermoplastic adhesive comprising a modified polyolefin resin having a branch chain having at least one carbonyl group and at least one benzene nucleus in one side chain. This adhesive shows a strong bonding force to a chlorine-containing polymer or an aromatic group-containing polymer such as a polyester and is especially valuable for the production of a laminate of such a resin and a polyolefin. A blend or block copolymer comprising an olefin resin component that can contain a carboxyl group and a carbon-to-carbon chain resin component having a benzoic acid ester or cinnamic acid ester group in the side chain is especially excellent in the bonding characteristics, particularly the heat-resistance adhesion.

  本发明公开了一种热塑性粘合剂，该粘合剂由改性聚烯烃树脂组成，改性聚烯烃树脂的一条侧链上具有至少一个羰基和至少一个苯核的支链。 这种粘合剂与含氯聚合物或含芳香族基团的聚合物（如聚酯）具有很强的粘合力，特别适用于生产这种树脂与聚烯烃的层压板。 由可含有羧基的烯烃树脂组分和侧链上具有苯甲酸酯或肉桂酸酯基团的碳-碳链树脂组分组成的共混物或嵌段共聚物在粘合特性，特别是耐热粘合性方面尤为出色。