2-[(3,5-Dinitrophenyl)sulfanyl]-1,3-benzothiazole | 176636-49-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(3,5-Dinitrophenyl)sulfanyl]-1,3-benzothiazole
• 英文别名: 2-(3,5-dinitrophenyl)sulfanyl-1,3-benzothiazole
• CAS: 176636-49-0
• 化学式: C₁₃H₇N₃O₄S₂
• 分子量: 333.348
• InChiKey: IEQWYJZOIWVFOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(3,5-Dinitrophenyl)sulfanyl]-1,3-benzothiazole 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 168.0h， 以58%的产率得到2-(3,5-dinitrophenylsulfinyl)-1,3-benzothiazole
  参考文献：
  名称：

  芳基3,5-二硝基苯基砜和亚砜的合成。3,5-二硝基二苯砜在与O-和S-亲核试剂反应中的转化

  摘要：

  1-Arylthio-3,5-dinitrobenzenes are selectively oxidized to the corresponding sulfones and sulfoxides by the action of hydrogen peroxide. Reactions of 3,5-dinitrodiphenyl sulfone with O- and S-centered nucleophiles (RXH, X = O, S) in dipolar aprotic solvents in the presence of K2CO3 result in replacement of the nitro group by the RX fragment; the reaction with methanol occurs in aqueous medium in the presence of NaHCO3. Substitution of the nitro group in 3,5-dinitrodiphenyl sulfone by phenylthio group, followed by oxidation of the sulfur atom to SO, and further replacement of the remaining nitro group yields 1,3,5-tris-(phenylsulfonyl)benzene. The phenylsulfonyl group in the latter is replaced by phenylthio group by reaction with PhSH in the presence of K2CO3. Mononitrosulfones obtained by nucleophilic substitution in the title compound can be reduced to the corresponding anilines.

  DOI：

  10.1023/a:1022563529344
• 作为产物：
  描述：

  1,3,5-三硝基苯 、 2-巯基苯并噻唑 在 potassium carbonate 作用下， 生成 2-[(3,5-Dinitrophenyl)sulfanyl]-1,3-benzothiazole
  参考文献：
  名称：

  Substitution of nitro groups in 1,3,5-trinitrobenzene and 2,4,6-trinitrotoluene under the action of thiophenols and their heterocyclic analogs

  摘要：

  DOI：

  10.1007/bf00713620

文献信息

• Substitution of nitro groups in 1,3,5-trinitrobenzene and 2,4,6-trinitrotoluene under the action of thiophenols and their heterocyclic analogs
  作者：S. A. Shevelev、M. D. Dutov、O. V. Serushkina

  DOI：10.1007/bf00713620

  日期：1995.12
• ——
  作者：O. V. Serushkina、M. D. Dutov、O. Yu. Sapozhnikov、B. I. Ugrak、S. A. Shevelev

  DOI：10.1023/a:1022563529344

  日期：——

  1-Arylthio-3,5-dinitrobenzenes are selectively oxidized to the corresponding sulfones and sulfoxides by the action of hydrogen peroxide. Reactions of 3,5-dinitrodiphenyl sulfone with O- and S-centered nucleophiles (RXH, X = O, S) in dipolar aprotic solvents in the presence of K2CO3 result in replacement of the nitro group by the RX fragment; the reaction with methanol occurs in aqueous medium in the presence of NaHCO3. Substitution of the nitro group in 3,5-dinitrodiphenyl sulfone by phenylthio group, followed by oxidation of the sulfur atom to SO, and further replacement of the remaining nitro group yields 1,3,5-tris-(phenylsulfonyl)benzene. The phenylsulfonyl group in the latter is replaced by phenylthio group by reaction with PhSH in the presence of K2CO3. Mononitrosulfones obtained by nucleophilic substitution in the title compound can be reduced to the corresponding anilines.