S-[2-(4-cyanophenyl)-2-oxoethyl] O-(1-methylethyl) carbonodithioate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-[2-(4-cyanophenyl)-2-oxoethyl] O-(1-methylethyl) carbonodithioate
• 英文别名: O-propan-2-yl [2-(4-cyanophenyl)-2-oxoethyl]sulfanylmethanethioate
• 化学式: C₁₃H₁₃NO₂S₂
• 分子量: 279.384
• InChiKey: BIFRZYMCBUUWDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-[2-(4-cyanophenyl)-2-oxoethyl] O-(1-methylethyl) carbonodithioate 在 硫酸 作用下， 反应 2.0h， 以82%的产率得到N-(1-methylethyl)-4-(2-oxo-1,3-dithiol-4-yl)benzamide
  参考文献：
  名称：

  UnexpectedRitterReaction During Acid-Promoted 1,3-Dithiol-2-one Formation

  摘要：

  AbstractA series of aryl‐substituted 1,3‐dithiol‐2‐ones was prepared by the BhattacharyaHortmann cyclization method. Unexpectedly, a Ritter reaction occurred during the acid‐catalyzed cyclization at the cyano group of the aryl substituents and 1,3‐dithiol‐2‐ones bearing a carboxy or a carboxamide group could be selectively obtained (see 1 and 2a in Scheme 1). The formation of the acid or the amide functionality was temperature‐dependent so that the one or the other group could be introduced selectively by modifying the reaction temperature.

  DOI：

  10.1002/hlca.201200311
• 作为产物：
  描述：

  对氰基苯乙酮 在 溴 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 20.0h， 生成 S-[2-(4-cyanophenyl)-2-oxoethyl] O-(1-methylethyl) carbonodithioate
  参考文献：
  名称：

  UnexpectedRitterReaction During Acid-Promoted 1,3-Dithiol-2-one Formation

  摘要：

  AbstractA series of aryl‐substituted 1,3‐dithiol‐2‐ones was prepared by the BhattacharyaHortmann cyclization method. Unexpectedly, a Ritter reaction occurred during the acid‐catalyzed cyclization at the cyano group of the aryl substituents and 1,3‐dithiol‐2‐ones bearing a carboxy or a carboxamide group could be selectively obtained (see 1 and 2a in Scheme 1). The formation of the acid or the amide functionality was temperature‐dependent so that the one or the other group could be introduced selectively by modifying the reaction temperature.

  DOI：

  10.1002/hlca.201200311

文献信息

• Unexpected<i>Ritter</i>Reaction During Acid-Promoted 1,3-Dithiol-2-one Formation
  作者：Frédéric Dumur、Cédric R. Mayer

  DOI：10.1002/hlca.201200311

  日期：2013.5

  AbstractA series of aryl‐substituted 1,3‐dithiol‐2‐ones was prepared by the BhattacharyaHortmann cyclization method. Unexpectedly, a Ritter reaction occurred during the acid‐catalyzed cyclization at the cyano group of the aryl substituents and 1,3‐dithiol‐2‐ones bearing a carboxy or a carboxamide group could be selectively obtained (see 1 and 2a in Scheme 1). The formation of the acid or the amide functionality was temperature‐dependent so that the one or the other group could be introduced selectively by modifying the reaction temperature.