2-Methoxycarbonyl-6-nitro-diphenylsulfid | 33358-47-3

• 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: 2-Methoxycarbonyl-6-nitro-diphenylsulfid
• 英文别名: 2-Nitro-6-carbomethoxydiphenylsulfid；Methyl 3-nitro-2-phenylsulfanylbenzoate
• CAS: 33358-47-3
• 化学式: C₁₄H₁₁NO₄S
• 分子量: 289.312
• InChiKey: DWLBPTIVIUREME-UHFFFAOYSA-N

物化性质

• 沸点：
  391.4±32.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-3-硝基苯甲酸甲酯 、 sodium thiophenolate 在 苯硫酚 作用下， 以 甲醇 为溶剂， 生成 2-Methoxycarbonyl-6-nitro-diphenylsulfid
  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

• 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 <i>o</i>-Carboxamido Group in S_NAr Reactions with an Anionic Nucleophile?
  作者：Caterina Arnone、Giovanni Consiglio、Vincenzo Frenna、Domenico Spinelli

  DOI：10.1021/jo961040h

  日期：1997.5.1

  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.