E-2-(cyclopropylmethylidene)thiosuccinic anhydride | 1244773-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: E-2-(cyclopropylmethylidene)thiosuccinic anhydride
• 英文别名: (3E)-3-(cyclopropylmethylidene)thiolane-2,5-dione
• CAS: 1244773-72-5
• 化学式: C₈H₈O₂S
• 分子量: 168.216
• InChiKey: WIWFBBJPAMZNLN-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  E-2-(cyclopropylmethylidene)thiosuccinic anhydride 、 1-[(2,4-二硝基苯基)磺酰基]哌啶 、 2-氨基苯硫醇 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 trans-N-[(benzo[b]-5-oxo-7-cyclopropyl-1,4-thiazepin-6-yl)acetyl]piperidine 、 trans-N-[(benzo[b]-5-oxo-7-cyclopropyl-1,4-thiazepin-6-yl)acetyl]piperidine
  参考文献：
  名称：

  Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: a convenient synthon for the preparation of substituted 1,4-thiazepin-5-ones and piperidinones via the intermediacy of thioacids

  摘要：

  Reaction of thiomaleic anhydride with triphenylphosphine gives the title compound, which undergoes reaction with a variety of aldehydes to give a range of alkylidene thiomaleic anhydrides (substituted monothioitaconic anhydrides). Subsequent treatment with tert-butoxycarbonylamino-substituted thiols, or under radical conditions with tert-butoxycarbonylamino-substituted alkyl halides results in a series of substituted monothiomaleic anhydrides, that on exposure to trifluoroacetic acid and then base lead to thiocarboxyl substituted 1,4-thiazepin-5-ones and piperidinones, respectively, that are ultimately trapped by reaction with 2,4-dinitrobenzenesulfonamides to give the corresponding amides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.002
• 作为产物：
  描述：

  dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione 、 环丙甲醛 反应 10.0h， 以84%的产率得到E-2-(cyclopropylmethylidene)thiosuccinic anhydride
  参考文献：
  名称：

  Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: a convenient synthon for the preparation of substituted 1,4-thiazepin-5-ones and piperidinones via the intermediacy of thioacids

  摘要：

  Reaction of thiomaleic anhydride with triphenylphosphine gives the title compound, which undergoes reaction with a variety of aldehydes to give a range of alkylidene thiomaleic anhydrides (substituted monothioitaconic anhydrides). Subsequent treatment with tert-butoxycarbonylamino-substituted thiols, or under radical conditions with tert-butoxycarbonylamino-substituted alkyl halides results in a series of substituted monothiomaleic anhydrides, that on exposure to trifluoroacetic acid and then base lead to thiocarboxyl substituted 1,4-thiazepin-5-ones and piperidinones, respectively, that are ultimately trapped by reaction with 2,4-dinitrobenzenesulfonamides to give the corresponding amides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.002

文献信息

• Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: a convenient synthon for the preparation of substituted 1,4-thiazepin-5-ones and piperidinones via the intermediacy of thioacids
  作者：David Crich、Md. Yeajur Rahaman

  DOI：10.1016/j.tet.2010.04.002

  日期：2010.8

  Reaction of thiomaleic anhydride with triphenylphosphine gives the title compound, which undergoes reaction with a variety of aldehydes to give a range of alkylidene thiomaleic anhydrides (substituted monothioitaconic anhydrides). Subsequent treatment with tert-butoxycarbonylamino-substituted thiols, or under radical conditions with tert-butoxycarbonylamino-substituted alkyl halides results in a series of substituted monothiomaleic anhydrides, that on exposure to trifluoroacetic acid and then base lead to thiocarboxyl substituted 1,4-thiazepin-5-ones and piperidinones, respectively, that are ultimately trapped by reaction with 2,4-dinitrobenzenesulfonamides to give the corresponding amides. (C) 2010 Elsevier Ltd. All rights reserved.