5-(4-chlorophenylthio)-5-oxopentanoic acid | 1247948-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: 5-(4-chlorophenylthio)-5-oxopentanoic acid
• 英文别名: 5-(4-Chlorophenyl)sulfanyl-5-oxopentanoic acid
• CAS: 1247948-35-1
• 化学式: C₁₁H₁₁ClO₃S
• 分子量: 258.726
• InChiKey: QFHJRNXVKBCJBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  戊二酸酐 、 4,4'-二氯二苯二硫醚 在 水 、 rongalite 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以82%的产率得到5-(4-chlorophenylthio)-5-oxopentanoic acid
  参考文献：
  名称：

  A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®

  摘要：

  Rongalite (R) promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.023

文献信息

• A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®
  作者：Weixing Dan、Hongjuan Deng、Jiuxi Chen、Miaochang Liu、Jinchang Ding、Huayue Wu

  DOI：10.1016/j.tet.2010.07.023

  日期：2010.9

  Rongalite (R) promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions. (C) 2010 Elsevier Ltd. All rights reserved.