S-(4-methylphenyl)-N,N-diethylcarbamate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-(4-methylphenyl)-N,N-diethylcarbamate
• 英文别名: S-p-tolyl diethylcarbamothioate；S-(4-methylphenyl) N,N-diethylcarbamothioate
• 化学式: C₁₂H₁₇NOS
• 分子量: 223.339
• InChiKey: PKLNORWPOKLFCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-二乙基甲酰胺 、 对甲苯磺酰肼 在 aluminum (III) chloride 、 DTBP 作用下， 反应 12.0h， 以54%的产率得到S-(4-methylphenyl)-N,N-diethylcarbamate
  参考文献：
  名称：

  AlCl3-promoted thiolation of acyl C–H bonds with arylsulfonyl hydrazides

  摘要：

  AlCl3-promoted thiolation of acyl C-H bonds with arylsulfonyl hydrazides was developed, which represents an effective synthesis of S-aryl thiocarbamates via C-S bond formation reaction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.030

文献信息

• A Facile Method for the Synthesis of Thiocarbamates:  Palladium-Catalyzed Reaction of Disulfide, Amine, and Carbon Monoxide
  作者：Yutaka Nishiyama、Hiroaki Kawamatsu、Noboru Sonoda

  DOI：10.1021/jo048350h

  日期：2005.4.1

  the synthesis of thiocarbamates has been developed. When dialkyl or diaryl disulfides were allowed to react with secondary amines and carbon monoxide in the presence of a catalytic amount of a palladium complex, the thiocarbamates were obtained in moderate to good yields. In contrast to that of secondary amines, in the reaction of a primary amine, no formation of thiocarbamate was confirmed, but urea

  已经开发了合成硫代氨基甲酸酯的新方法。当在催化量的钯配合物存在下使二烷基或二芳基二硫化物与仲胺和一氧化碳反应时，以中等至良好的产率获得了硫代氨基甲酸酯。与仲胺相反，在伯胺的反应中，未确认到硫代氨基甲酸酯的形成，但是以高收率形成了尿素。
• Palladium-Catalyzed Azathiolation of Carbon Monoxide
  作者：Hitoshi Kuniyasu、Hiroshi Hiraike、Masaki Morita、Aoi Tanaka、Kunihiko Sugoh、Hideo Kurosawa

  DOI：10.1021/jo9823137

  日期：1999.10.1

  A novel palladium-catalyzed azathiolation of carbon monoxide using sulfenamide (RSNR'(2)) (1) is described to provide thiocarbamate 2 in good yields. The mechanistic proposal includes the following: (1) insertion of CO into Pd-S bond of Pd(SR)(2)(PPh3)(n) 4 to provide Pd[C(O)SR](SR)-(PPh3)(n) 5 and (2) sigma-bond metathesis between S-N and Pd-C(O) bonds to afford 2 with the regeneration of 4.