(S)-2-Vinyl-cyclopropane-1,1-dicarboxylic acid | 53376-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-Vinyl-cyclopropane-1,1-dicarboxylic acid
• 英文别名: (2S)-2-ethenylcyclopropane-1,1-dicarboxylic acid
• CAS: 53376-54-8
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: AFEWNSCLQLQUEJ-SCSAIBSYSA-N

物化性质

• 沸点：
  348.9±42.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Vinyl-cyclopropane-1,1-dicarboxylic acid 以 乙醚 为溶剂， 生成 (1R,2R)-3-Oxo-2-(2-pentinyl)cyclopentanessigsaeure-methylester
  参考文献：
  名称：

  Quinkert, Gerhard; Adam, Friedhelm; Duerner, Gerd, Angewandte Chemie, 1982, vol. 94, # 11, p. 866 - 867

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2-Vinyl-1,1-cyclopropandicarbonsaeure-bis[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl]ester 生成 (S)-2-Vinyl-cyclopropane-1,1-dicarboxylic acid
  参考文献：
  名称：

  Quinkert, Gerhard; Schmalz, Hans-Guenther; Dzierzynski, Elmar M., Angewandte Chemie, 1986, vol. 98, # 11, p. 1023 - 1024

  摘要：

  DOI：

文献信息

• A Practical Asymmetric Synthesis of Isopropyl (1<i>R</i>,2<i>S</i>)-Dehydrocoronamate
  作者：Wenjun Tang、Xudong Wei、Nathan K. Yee、Nitinchandra Patel、Heewon Lee、Jolaine Savoie、Chris H. Senanayake

  DOI：10.1021/op200038y

  日期：2011.9.16

  A novel asymmetric synthesis of isopropyl (1R,2S)-dehydrocoronamate is described from (S)-1,2,4-butanetriol as the starting material in 28% overall yield. Highlights of this synthetic route include selective cyclopropanation between chiral cyclic sulfate 5 and diisopropyl malonate (8c), formation of vinylcyclopropane 3c via elimination of halide 4c, selective monohydrolysis of diisopropyl ester 3c

  以（S）-1，2，4-丁三醇为起始原料，以28％的总收率描述了异丙基（1 R，2 S）-脱氢冕酸异丙酯的新型不对称合成。此合成途径的重点包括手性环硫酸酯之间的选择性环丙烷化5和二异丙基丙二酸二乙酯（图8c），形成乙烯基环丙烷的3C卤化物通过消除4c中，二异丙基酯的选择性单水解3C，和的酸Curtius重排10以形成异丙基（1 - [R ，2 S）-脱氢日冕酸盐TsOH盐13在> 99％ee中。仅涉及三个分离，该无色谱方法提供了快速和实用的获得（1 R，2 S）-1-氨基-2-乙烯基环丙烷-1-羧酸衍生物的途径。
• Kinetic Analysis of a Cysteine-Derived Thiyl-Catalyzed Asymmetric Vinylcyclopropane Cycloaddition Reflects Numerous Attractive Noncovalent Interactions
  作者：Amanda K. Turek、Marcus H. Sak、Scott J. Miller

  DOI：10.1021/jacs.1c07323

  日期：2021.10.6

  Kinetic studies of a vinylcyclopropane (VCP) cycloaddition, catalyzed by peptide-based thiyl radicals, are described. Reactions were analyzed by using reaction progress kinetic analysis, revealing that ring-opening of the VCP is both rate- and enantio-determining. These conclusions are further corroborated by studies involving racemic and enantiopure VCP starting material. Noncovalent interactions

  描述了由基于肽的硫自由基催化的乙烯基环丙烷 (VCP) 环加成的动力学研究。通过使用反应进程动力学分析来分析反应，揭示了 VCP 的开环是速率和对映体决定的。涉及外消旋和对映纯 VCP 起始材料的研究进一步证实了这些结论。非共价相互作用在整个过程中发挥着关键作用：肽催化剂和 VCP 都表现出非生产性的自聚集，这似乎被催化剂和 VCP 之间的结合所破坏。这反过来解释了对关键催化剂特征的要求，即脯氨酸残基 4 位上的取代基，这是周转率/速率和选择性所必需的。
• PROCESS FOR RESOLVING RACEMIC MIXTURES AND A DIASTEREOISOMERIC COMPLEX OF A RESOLVING AGENT AND AN ENANTIOMER OF INTEREST
  申请人：Napolitano Elio

  公开号：US20090292129A1

  公开（公告）日：2009-11-26

  A process for resolving a compound in racemic form comprising the following steps is described: a) reacting a compound in racemic form with a resolving agent, b) forming a diastereoisomeric complex of the resolving agent and an enantiomer of interest, c) separating the enantiomer of interest from the obtained diastereoisomer, wherein such a process is characterized in that said resolving agent is a compound of Formula (I). A diastereoisomeric complex between the resolving agent of Formula (I) and the enantiomer of interest is also described. The process according to the invention allows acid and basic racemic mixtures to be separated.

  本发明提供了一种用于分离外消旋化合物的方法，包括以下步骤：a）将外消旋化合物与分离剂反应，b）形成分离剂和所需对映体的非对映异构体复合物，c）从所得的非对映异构体中分离所需对映体。其中，所述分离剂为式（I）的化合物。本发明还描述了分离剂式（I）与所需对映体之间的非对映异构体复合物。本发明所述方法可以分离酸性和碱性外消旋混合物。
• NOVEL HYDROLASE PROTEIN
  申请人：Kawabata Hiroshi

  公开号：US20130130338A1

  公开（公告）日：2013-05-23

  It is an object of the present invention to provide a novel hydrolase, which is used when dialkyl 2-vinylcyclopropane-1,1-dicarboxylate is hydrolyzed with an enzyme, so as to efficiently obtain (1S,2S)-1-alkoxycarbonyl-2-vinylcyclopropanecarboxylic acid that is useful as an intermediate for synthesizing therapeutic agents for hepatitis C. According to the present invention, there is provided a hydrolase protein, which consists of the amino acid sequence shown in any one of SEQ ID NOS. 2 to 5 and which has activity of catalyzing, at higher selectivity than the protein consisting of the amino acid sequence shown in SEQ ID NO. 1, a reaction of producing (1S,2S)-1-ethoxycarbonyl-2-vinylcyclopropanecarboxylic acid from diethyl 2-vinylcyclopropane-1,1-dicarboxylate.

  本发明的目的是提供一种新型的水解酶，当用酶水解二烷基2-乙烯基环丙烷-1,1-二甲酸酯时，可高效地获得(1S,2S)-1-烷氧羰基-2-乙烯基环丙烷羧酸，该化合物是合成治疗丙型肝炎药物的中间体。根据本发明，提供了一种水解酶蛋白，其由SEQ ID NO. 2到5中任一序列所示的氨基酸序列组成，具有在比SEQ ID NO. 1中所示的氨基酸序列组成的蛋白质更高的选择性催化反应，从二乙酸2-乙烯基环丙烷-1,1-二甲酸酯中产生(1S,2S)-1-乙氧羰基-2-乙烯基环丙烷羧酸。
• NOVEL HYDROLASE AND METHOD FOR PRODUCING (1S,2S)-1-ALKOXYCARBONYL-2-VINYLCYCLOPROPANE CARBOXYLIC ACID USING SAME
  申请人：API Corporation

  公开号：EP3778898A1

  公开（公告）日：2021-02-17

  The present invention provides a novel hydrolase that can industrially produce optically highly pure (1S,2S)-1-alkoxycarbonyl-2-vinylcyclopropane carboxylic acid with high efficiency at low costs, and a production method using the hydrolase.

  本发明提供了一种新型水解酶，它能以低成本高效率地工业化生产光学高纯度的(1S,2S)-1-烷氧基羰基-2-乙烯基环丙烷羧酸，并提供了一种使用该水解酶的生产方法。