methyl ((phenylthio)carbonyl)glycinate | 99060-54-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl ((phenylthio)carbonyl)glycinate
• 英文别名: Methyl 2-(phenylsulfanylcarbonylamino)acetate
• CAS: 99060-54-5
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: DZMGDZKHIJRPBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯二硫醚 在 N-溴代丁二酰亚胺(NBS) 、 sodium iodide 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 28.0h， 生成 isopropyl benzenesulfinate 、 methyl ((phenylthio)carbonyl)glycinate
  参考文献：
  名称：

  异氰酸酯和硫代磺酸盐的碘化物催化合成仲硫代氨基甲酸盐

  摘要：

  报道了一种从易得的异氰酸酯和具有宽泛的官能团耐受性的硫代磺酸盐合成仲硫代氨基甲酸酯的新方法。该反应在温和的反应条件下在异丙醇中进行，并由廉价的碘化钠催化。

  DOI：

  10.1021/acs.orglett.6b01023

文献信息

• Molecular iodine-mediated synthesis of thiocarbamates from thiols, isocyanides and water under metal-free conditions
  作者：Wen-Hu Bao、Chao Wu、Jing-Ting Wang、Wen Xia、Ping Chen、Zilong Tang、Xinhua Xu、Wei-Min He

  DOI：10.1039/c8ob01820k

  日期：——

  A metal-free and efficient molecular iodine-mediated protocol has been developed to prepare thiocarbamates from readily available thiols, isocyanides and water.

  已开发出一种无金属、高效的分子碘介导的方法，可从易得的硫醇、异氰酸酯和水中制备硫代氨基甲酸酯。
• Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of <i>S</i>-thiocarbamates
  作者：Ramdas S. Pathare、Vikas Patil、Harpreet Kaur、Antim K. Maurya、Vijai K. Agnihotri、Shahnawaz Khan、Nagaraju Devunuri、Ashoke Sharon、Devesh M. Sawant

  DOI：10.1039/c8ob01855c

  日期：——

  A novel and efficient metal free, redox-neutral method for the synthesis of secondary thiocarbamates by cross-coupling of readily available thiophenol and isocyanides has been developed. The present methodology exhibits a broad substrate scope with good to excellent yields without an additive/extra oxidant under mild reaction conditions catalyzed by inexpensive iodine as the catalyst.

  已经开发了一种新颖且有效的无金属，氧化还原中性的方法，该方法通过将易得的硫酚和异氰酸酯交叉偶联来合成仲硫代氨基甲酸酯。在廉价的碘作为催化剂催化的温和反应条件下，本方法学显示出宽范围的底物范围，具有良好至优异的收率，而没有添加剂/额外的氧化剂。
• 461. Cytotoxic compounds. Part III. Some derivatives of p-(NN-di-2-chloroethyl- and of p,-(NN-di-2-bromoethyl-amino)thiophenol
  作者：A. M. Creighton、L. N. Owen、G. R. White

  DOI：10.1039/jr9610002375

  日期：——
• Clean preparation of S-thiocarbamates with in situ generated hydroxide in 2-methyltetrahydrofuran
  作者：Wen-Hu Bao、Zheng Wang、Xiao Tang、Yun-Fu Zhang、Jia-Xi Tan、Qin Zhu、Zhong Cao、Ying-Wu Lin、Wei-Min He

  DOI：10.1016/j.cclet.2019.06.052

  日期：2019.12

  A simple and clean protocol for the synthesis of various alkyl and (hetero)aryl S-thiocarbamates was established. The usage of in situ generated hydroxide as both an oxygen source and hydrogen source as well as biomass-derived 2-methyltetrahydrofuran as a green reaction medium, the avoidance of phosphorus-containing reductant, and the generation of harmless water and nitrogen as the side-products have given the present method atom-economy and environmental friendliness. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.