cyano(ethoxycarbonothioylthio)methyl benzoate | 875559-55-0

• 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: cyano(ethoxycarbonothioylthio)methyl benzoate
• 英文别名: [Cyano(ethoxycarbothioylsulfanyl)methyl] benzoate
• CAS: 875559-55-0
• 化学式: C₁₂H₁₁NO₃S₂
• 分子量: 281.356
• InChiKey: SCRAOVNVJPTOLO-UHFFFAOYSA-N

物化性质

• 沸点：
  445.7±40.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyano(ethoxycarbonothioylthio)methyl benzoate 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 、 异丙醇 为溶剂， 生成 1-cyanoctylbenzoate
  参考文献：
  名称：

  Cyano(ethoxycarbonothioylthio)methyl Benzoate:  A Novel One-Carbon Radical Equivalent

  摘要：

  Cyano(ethoxycarbonothioylthio)methyl benzoate 3 has been prepared and shown to be an excellent one-carbon radical equivalent that can be applied for the introduction of an acyl unit via xanthate transfer radical addition to olefins. The corresponding adducts can be further elaborated. A rare 1,5-nitrile translocation was also observed during the study.

  DOI：

  10.1021/ol052634m
• 作为产物：
  描述：

  苯甲酸 氰基甲酯 、 potassium ethyl xanthogenate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 23.0h， 以7.2 g的产率得到cyano(ethoxycarbonothioylthio)methyl benzoate
  参考文献：
  名称：

  Cyano(ethoxycarbonothioylthio)methyl Benzoate:  A Novel One-Carbon Radical Equivalent

  摘要：

  Cyano(ethoxycarbonothioylthio)methyl benzoate 3 has been prepared and shown to be an excellent one-carbon radical equivalent that can be applied for the introduction of an acyl unit via xanthate transfer radical addition to olefins. The corresponding adducts can be further elaborated. A rare 1,5-nitrile translocation was also observed during the study.

  DOI：

  10.1021/ol052634m

文献信息

• A Convergent Synthesis of Enantiopure Open-Chain, Cyclic, and Fluorinated α-Amino Acids
  作者：Shi-Guang Li、Fernando Portela-Cubillo、Samir Z. Zard

  DOI：10.1021/acs.orglett.6b00656

  日期：2016.4.15

  A radical based synthesis of a broad variety of protected enantiopure α-amino acids, including fluorinated derivatives, is described. The radical addition furnishes naturally latent mercapto-α-amino acids ideally equipped for native chemical ligation.

  描述了自由基保护的多种受保护的对映纯α-氨基酸（包括氟化衍生物）的合成。自由基的加成提供了天然潜伏的巯基-α-氨基酸，非常适合天然化学连接。
• Stabilization of Radicals by Imides. A Modular Stereoselective Approach to Protected Functional 1,2-Diamines
  作者：Songzhe Han、Samir Z. Zard

  DOI：10.1021/ol502599r

  日期：2014.10.17

  Radical addition of various xanthates to N,N'-diacylimidazol-2-one occurs readily to give protected 1,2-diamines. The imide group stabilizes the adduct radical sufficiently to enable a second addition to unactivated alkenes. In some cases, the addition product could be converted into an indoline, a tetralone, or further added to an indole. Regioselective removal of one acyl group could also be accomplished.
• A flexible radical approach to 5-substituted 4,5-dihydro-3H-pyrido[4,3-b]azepin-2-ones. Some mechanistic observations on the radical cyclisation-aromatisation process
  作者：Laurent Petit、Iuliana Botez、André Tizot、Samir Z. Zard

  DOI：10.1016/j.tetlet.2012.04.020

  日期：2012.6

  Variously substituted novel dihydropyridoazepinones have been prepared by an intermolecular radical addition followed by a radical cyclisation on a pyridine ring. The latter process involved the use of a combination of two different peroxides, an experimental contrivance resulting from a careful product analysis and a better understanding of the cyclisation step. (C) 2012 Elsevier Ltd. All rights reserved.
• Cyano(ethoxycarbonothioylthio)methyl Benzoate:  A Novel One-Carbon Radical Equivalent
  作者：Sharanjeet K. Bagal、Michiel de Greef、Samir Z. Zard

  DOI：10.1021/ol052634m

  日期：2006.1.1

  Cyano(ethoxycarbonothioylthio)methyl benzoate 3 has been prepared and shown to be an excellent one-carbon radical equivalent that can be applied for the introduction of an acyl unit via xanthate transfer radical addition to olefins. The corresponding adducts can be further elaborated. A rare 1,5-nitrile translocation was also observed during the study.