S-(4-methoxyphenyl) 4-chlorobenzothioate | 1258145-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-(4-methoxyphenyl) 4-chlorobenzothioate
• 英文别名: S-(4-methoxyphenyl) 4-chlorobenzenecarbothioate
• CAS: 1258145-47-9
• 化学式: C₁₄H₁₁ClO₂S
• 分子量: 278.759
• InChiKey: CATOUPDKTIMQSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  六氟苯 、 S-(4-methoxyphenyl) 4-chlorobenzothioate 在 hydridotetakis(triphenylphosphine)rhodium(I) 、 1,2-双(二苯基膦)乙烷 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以30%的产率得到4-chlorobenzoyl fluoride
  参考文献：
  名称：

  Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors

  摘要：

  A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh3)(4)-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6-tetrafluorobenzenes. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.09.009
• 作为产物：
  描述：

  4-氯苯甲酰氯 在 4-二甲氨基吡啶 、 potassium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 S-(4-methoxyphenyl) 4-chlorobenzothioate
  参考文献：
  名称：

  在温和条件下将酯转化为硫酯

  摘要：

  我们报道在无过渡金属的条件下，通过选择性的C–O键断裂/弱的C–S键形成，酯转化为硫酯。该方法以通用且实用的无过渡金属体系，广泛的底物范围和出色的官能团耐受性而著称。该策略已成功地用于后期硫酯化，定点交叉偶联/硫酯化/脱羰和易于处理的克级硫酯化中。进行了选择性和计算研究，以了解通过C-O键裂解形成的弱C-S键的现象，这与向羧酸衍生物中亲核加成的传统趋势形成了鲜明的对比。

  DOI：

  10.1039/d1ob00187f

文献信息

• Conversion of esters to thioesters under mild conditions
  作者：Yijun Shi、Xuejing Liu、Han Cao、Fusheng Bie、Ying Han、Peng Yan、Roman Szostak、Michal Szostak、Chengwei Liu

  DOI：10.1039/d1ob00187f

  日期：——

  We report conversion of esters to thioesters via selective C–O bond cleavage/weak C–S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterifi

  我们报道在无过渡金属的条件下，通过选择性的C–O键断裂/弱的C–S键形成，酯转化为硫酯。该方法以通用且实用的无过渡金属体系，广泛的底物范围和出色的官能团耐受性而著称。该策略已成功地用于后期硫酯化，定点交叉偶联/硫酯化/脱羰和易于处理的克级硫酯化中。进行了选择性和计算研究，以了解通过C-O键裂解形成的弱C-S键的现象，这与向羧酸衍生物中亲核加成的传统趋势形成了鲜明的对比。
• Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors
  作者：Mieko Arisawa、Toru Yamada、Masahiko Yamaguchi

  DOI：10.1016/j.tetlet.2010.09.009

  日期：2010.11

  A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh3)(4)-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6-tetrafluorobenzenes. (C) 2010 Published by Elsevier Ltd.