ethyl 3-(carboxymethylthio)-2-cyanopropionate | 139022-55-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(carboxymethylthio)-2-cyanopropionate
• 英文别名: 2-(2-Cyano-3-ethoxy-3-oxopropyl)sulfanylacetic acid
• CAS: 139022-55-2
• 化学式: C₈H₁₁NO₄S
• 分子量: 217.246
• InChiKey: HOKBYVFYZSPGFM-UHFFFAOYSA-N

物化性质

• 沸点：
  422.8±45.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氰基丙烯酸乙酯 、 巯基乙酸 以 丙酮 为溶剂， 反应 2.0h， 以95%的产率得到ethyl 3-(carboxymethylthio)-2-cyanopropionate
  参考文献：
  名称：

  Reaction of ?-cyanoacrylates with functionally substituted thiols, ethanedithiol, and hydrogen sulfide

  摘要：

  Functionally substituted thiols, i.e., thioglycolic acid and cysteamine and cysteine hydrochlorides, facilely undergo addition at the double bond of alpha-cyanoacrylates, forming the corresponding adducts in quantitative yields: R'SCH2CH(CN)COOR [R' = CH2COOH; CH2CH2NH2.HCl; CH2CH(COOH)NH2-HCl]. Under similar conditions, the reaction with ethanedithiol gives the diadduct [CH2SCH2CH(CN)COOR)2; the monoadduct HSCH2CH2SCH2CH(CN)COOR is formed in a significantly lower yield. Hydrogen sulfide does not undergo addition to alpha-cyanoacrylate in the absence of a catalyst; S[CH2CH(CN)COOR]2 is formed quantitatively in the presence of Et3N. In the presence of triethylamine, this sulfide undergoes intramolecular cyclization (the Ziegler-Thorpe reaction) with formation of 4-amino-5-cyano-3,5-bis(ethoxycarbonyl)thiacyclohex-3-ene.

  DOI：

  10.1007/bf00959721

文献信息

• Reaction of ?-cyanoacrylates with functionally substituted thiols, ethanedithiol, and hydrogen sulfide
  作者：I. I. Kandror、I. O. Bragina、M. A. Galkina、T. I. Guseva、B. D. Lavrukhin、Yu. G. Gololobov

  DOI：10.1007/bf00959721

  日期：1991.12

  Functionally substituted thiols, i.e., thioglycolic acid and cysteamine and cysteine hydrochlorides, facilely undergo addition at the double bond of alpha-cyanoacrylates, forming the corresponding adducts in quantitative yields: R'SCH2CH(CN)COOR [R' = CH2COOH; CH2CH2NH2.HCl; CH2CH(COOH)NH2-HCl]. Under similar conditions, the reaction with ethanedithiol gives the diadduct [CH2SCH2CH(CN)COOR)2; the monoadduct HSCH2CH2SCH2CH(CN)COOR is formed in a significantly lower yield. Hydrogen sulfide does not undergo addition to alpha-cyanoacrylate in the absence of a catalyst; S[CH2CH(CN)COOR]2 is formed quantitatively in the presence of Et3N. In the presence of triethylamine, this sulfide undergoes intramolecular cyclization (the Ziegler-Thorpe reaction) with formation of 4-amino-5-cyano-3,5-bis(ethoxycarbonyl)thiacyclohex-3-ene.