3-Nitro-4-(phenylthio)benzamide | 189125-10-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-Nitro-4-(phenylthio)benzamide
• 英文别名: 3-nitro-4-phenylsulfanylbenzamide
• CAS: 189125-10-8
• 化学式: C₁₃H₁₀N₂O₃S
• 分子量: 274.3
• InChiKey: CNZMLIHIMVFISX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium thiophenolate 、 3-硝基-4-碘苯甲酰胺 在 苯硫酚 作用下， 以 甲醇 为溶剂， 生成 3-Nitro-4-(phenylthio)benzamide
  参考文献：
  名称：

  Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an “Inverted Built-In Solvation” Be Responsible for the Peculiar Activation by an o-Carboxamido Group in S_NAr Reactions with an Anionic Nucleophile?

  摘要：

  A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (k(CONH2)/k(CO2Me) 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (kCONH(2)/k(CO2Me) 0.14) in the reactions with the same nucleophile has been observed when they are in a para-position. Moreover, for piperidino-dehalogenation reactions in methanol k(CONH2)/k(CO2Me) ratios less than unity (0.2-0.6) have been observed independently of the position (ortho or para) of the carboxamido and carbomethoxy groups with respect to the reaction center.

  DOI：

  10.1021/jo961040h

文献信息

• ANTI-VIRAL COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP1979348B1

  公开（公告）日：2012-01-18