S-methyl (4-nitrophenyl)carbamothioate | 34277-69-5

• 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-methyl (4-nitrophenyl)carbamothioate
• 英文别名: S-methyl 4-nitrophenylcarbamothioate；S-methyl N-(4-nitrophenyl)carbamothioate
• CAS: 34277-69-5
• 化学式: C₈H₈N₂O₃S
• 分子量: 212.229
• InChiKey: KBAFQTTWXUQBNN-UHFFFAOYSA-N

物化性质

• 熔点：
  197-199 °C
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl N'-(4-nitrophenyl)carbamimidothioate;hydroiodide 在 水 作用下， 生成 S-methyl (4-nitrophenyl)carbamothioate
  参考文献：
  名称：

  Reaction of S-methiodide derivatives of activated thioureas with hydroxylic compounds. Novel synthesis of mercaptans

  摘要：

  DOI：

  10.1021/jo00975a015

文献信息

• Glycosyl alkoxythioimidates as building blocks for glycosylation: a reactivity study
  作者：Sneha C. Ranade、Alexei V. Demchenko

  DOI：10.1016/j.carres.2014.06.025

  日期：2015.2

  Structural modifications of the leaving group of S-glycosyl O-methyl phenylcarbamothioates (SNea) involving change of substituents that express different electronic effects led to a better understanding of how the reactivity of these glycosyl donors can be modified by changing the structure of their leaving groups. Mechanistic studies involving the isolation of departed aglycones were indicative of

  S-糖基O-甲基苯基氨基甲磺酸酯（SNea）的离去基团的结构修饰涉及到表现出不同电子效应的取代基的变化，从而使人们对如何通过改变其离去基团的结构来修饰这些糖基供体的反应性有了更好的理解。 。涉及离去的糖苷配基分离的机理研究表明，通过异头硫而不是远端氮原子直接激活对甲氧基-SNea和对硝基-SNea离开基团。给电子取代基（对甲氧基）的存在对硫原子的亲核性具有强烈的影响，该硫原子的亲核性尤其容易受到亲硫试剂的攻击。该关键观察结果使得能够区分对甲氧基-SNea与对硝基-SNea以及甚至未修饰的SNea离去基团的反应性水平。在一系列SNea离去基团中观察到的反应性差异足以通过选择性激活策略用于快速寡糖合成。
• Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: a route to diversely substituted S-alkylcarbamothioates
  作者：Abdallah Larbi Doukara、Mohammed Amine Mehdid、Ayada Djafri、Federico Andreoli、Nicolas Vanthuyne、Christian Roussel

  DOI：10.1016/j.tet.2010.01.020

  日期：2010.3

  A new route to S-alkylcarbamothioates is disclosed. In a first step, N-(2-aminophenyl)-4-methyl-thiazolin-2-thione is transformed into a mono- or disubstituted urea at nitrogen, and then in a second step, alkylated at sulfur. The resulting salts, after treatment with a base, gave S-alkylcarbamothioates in high isolated yields together with 3-methyl[1,3]thiazolo[3,2-a]benzimidazole under very mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.