(Z)-1-carbamoyl-2-ethenylcyclopropanecarboxylic acid

• 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: (Z)-1-carbamoyl-2-ethenylcyclopropanecarboxylic acid
• 英文别名: 2-vinyl-1-carbamoylcyclopropanecarboxylic acid；(1R,2R)-1-carbamoyl-2-ethenylcyclopropane-1-carboxylic acid
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: VZWWEPVRXYJINZ-MHTLYPKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-carbamoyl-2-ethenylcyclopropanecarboxylic acid 在 次氯酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 7.0h， 生成 (1R,2S)-1-叔丁氧羰基氨基-2-乙烯基环丙烷甲酸
  参考文献：
  名称：

  EP2345633

  摘要：

  公开号：
• 作为产物：
  描述：

  2-乙烯基环丙烷-1,1-二羧酸二甲酯 在 sodium hydroxide 、 氨 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 (Z)-1-carbamoyl-2-ethenylcyclopropanecarboxylic acid
  参考文献：
  名称：

  A Convenient Synthesis of Methyl (Z)-1-Carbamoyl-2-ethenylcyclopropanecarboxylate and (Z)-1-Carbamoyl-2-ethenylcyclopropanecarboxylic Acid

  摘要：

  A simple method for the preparation of the title compounds via the reaction of dimethyl 2-ethenylcyclopropane-1,1-dicarboxylate with 6M ammonia in methanol is described.

  DOI：

  10.1080/00397919408010556

文献信息

• METHOD FOR PRODUCING OPTICALLY ACTIVE VINYLCYCLOPROPANECARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE VINYLCYCLOPROPANEAMINO ACID DERIVATIVE
  申请人：Tanaka Tatsuyoshi

  公开号：US20110245529A1

  公开（公告）日：2011-10-06

  The objective of the present invention is to provide a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative with high yield and high optical purity using a safe material available at low cost. In addition, the objective of the present invention is to provide a method for safely-obtaining an optically active vinylcyclopropaneamino acid with high optical purity at low cost. The problems can be solved by a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative, which method contains the step of reacting a racemic vinylcyclopropanecarboxylic acid derivative with an optically active amine compound, to obtain a diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound. In addition, it is possible to obtain a vinylcyclopropaneamino acid by deriving the vinylcyclopropaneamino acid from thus obtained diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative-amine compound.

  本发明的目的是提供一种方法，使用成本低廉的安全材料高产高光学纯度地获得光学活性的乙烯基环丙烷羧酸衍生物。此外，本发明的目的还是提供一种以低成本安全地获得高光学纯度的光学活性乙烯基环丙烷氨基酸的方法。这些问题可以通过一种方法来解决，该方法包含将外消旋的乙烯基环丙烷羧酸衍生物与光学活性胺化合物反应，以获得光学活性乙烯基环丙烷羧酸衍生物-胺化合物的对映异构体盐。此外，可以通过从所获得的光学活性乙烯基环丙烷羧酸衍生物-胺化合物的对映异构体盐中推导出乙烯基环丙烷氨基酸。
• OPTICALLY ACTIVE VINYL-CYCLOPROPANE CARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE VINYL-CYCLOPROPANE AMINO ACID DERIVATIVE MANUFACTURING METHOD
  申请人：Kaneka Corporation

  公开号：EP2345633A1

  公开（公告）日：2011-07-20

  The objective of the present invention is to provide a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative with high yield and high optical purity using a safe material available at low cost. In addition, the objective of the present invention is to provide a method for safely-obtaining an optically active vinylcyclopropaneamino acid with high optical purity at low cost. The problems can be solved by a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative, which method contains the step of reacting a racemic vinylcyclopropanecarboxylic acid derivative with an optically active amine compound, to obtain a diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative - amine compound. In addition, it is possible to obtain a vinylcyclopropaneamino acid by deriving the vinylcyclopropaneamino acid from thus obtained diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative - amine compound.

  本发明的目的是提供一种利用低成本安全材料获得高产率和高光学纯度的光学活性乙烯基环丙烷羧酸衍生物的方法。此外，本发明的目的是提供一种以低成本安全地获得光学活性高光学纯度的乙烯基环丙烷氨基 酸的方法。这些问题可以通过一种获得光学活性乙烯基环丙烷羧酸衍生物的方法来解决，该方法包含以下步骤：将外消旋乙烯基环丙烷羧酸衍生物与光学活性胺化合物反应，得到光学活性乙烯基环丙烷羧酸衍生物-胺化合物的非对映异构盐。此外，还可以从这样得到的光学活性乙烯基环丙烷羧酸衍生物-胺化合物的非对映异构盐中得到乙烯基环丙烷氨基酸。
• Galgoci Michelle, Davidson Janel E., Harrington Clinton K., Hasha Dennis +, Synth. Commun, 24 (1994) N 17, S 2477-2483
  作者：Galgoci Michelle, Davidson Janel E., Harrington Clinton K., Hasha Dennis +

  DOI：——

  日期：——
• EP2345633
  申请人：——

  公开号：——

  公开（公告）日：——
• A Convenient Synthesis of Methyl (<i>Z</i>)-1-Carbamoyl-2-ethenylcyclopropanecarboxylate and (<i>Z</i>)-1-Carbamoyl-2-ethenylcyclopropanecarboxylic Acid
  作者：Michelle Galgoci、Janel E. Davidson、Clinton K. Harrington、Dennis L. Hasha、Christian T. Goralski

  DOI：10.1080/00397919408010556

  日期：1994.9

  A simple method for the preparation of the title compounds via the reaction of dimethyl 2-ethenylcyclopropane-1,1-dicarboxylate with 6M ammonia in methanol is described.