3-[bis(methylthio)methylene]-2-benzofuran-1(3H)-one | 197715-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 3-[bis(methylthio)methylene]-2-benzofuran-1(3H)-one
• 英文别名: 3-[bis(methylsulfanyl)methylidene]-2-benzofuran-1-one
• CAS: 197715-04-1
• 化学式: C₁₁H₁₀O₂S₂
• 分子量: 238.331
• InChiKey: IKLPHROSFPSNCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[bis(methylthio)methylene]-2-benzofuran-1(3H)-one 、 2-甲基哌啶 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以37.7%的产率得到1-[2-(2-methylpiperidine-1-carbonyl)phenyl]-2,2-bis(methylsulfanyl)ethanone
  参考文献：
  名称：

  Synthese und Reaktionsverhalten von 3-(Bis(alkylthio)methylen)-3H-isobenzofuran-1-on-und 2-(Bis(alkylthio)methylen)-3(2H)-benzofuranon-Derivaten

  摘要：

  3(Bis(alkylthio)methylene)-3H-isobenzofuran-1-ones 2a-e and 2-(bis(alkylthio)methylene)-3(2H)-benzofuranone derivatives 4a-c are obtained by reaction of phthalides 1a-d or 3(2H)-benzofuranone (coumaranone 3), respectively, with carbon disulfide under basic conditions followed by alkylation. The reaction behaviour of the new compounds 2 and 4 is investigated. 2-((2-Dimethylthio-1-oxo)ethyl)benzoic acid N,N-dimethylamide (7a) and 2-((2-dimethylthio-1-oxo)ethyl)-benzoic acid 2-methylpiperidide (7b) are surprisingly formed instead of the methylthio substitution products by treatment of 2a with the corresponding amine in the presence of aluminum chloride.

  DOI：

  10.1007/bf00810773
• 作为产物：
  描述：

  二硫化碳 、 苯酞 、 碘甲烷 在 potassium tert-butylate 作用下， 生成 3-[bis(methylthio)methylene]-2-benzofuran-1(3H)-one
  参考文献：
  名称：

  Synthese und Reaktionsverhalten von 3-(Bis(alkylthio)methylen)-3H-isobenzofuran-1-on-und 2-(Bis(alkylthio)methylen)-3(2H)-benzofuranon-Derivaten

  摘要：

  3(Bis(alkylthio)methylene)-3H-isobenzofuran-1-ones 2a-e and 2-(bis(alkylthio)methylene)-3(2H)-benzofuranone derivatives 4a-c are obtained by reaction of phthalides 1a-d or 3(2H)-benzofuranone (coumaranone 3), respectively, with carbon disulfide under basic conditions followed by alkylation. The reaction behaviour of the new compounds 2 and 4 is investigated. 2-((2-Dimethylthio-1-oxo)ethyl)benzoic acid N,N-dimethylamide (7a) and 2-((2-dimethylthio-1-oxo)ethyl)-benzoic acid 2-methylpiperidide (7b) are surprisingly formed instead of the methylthio substitution products by treatment of 2a with the corresponding amine in the presence of aluminum chloride.

  DOI：

  10.1007/bf00810773

文献信息

• Synthese und Reaktionsverhalten von 3-(Bis(alkylthio)methylen)-3H-isobenzofuran-1-on-und 2-(Bis(alkylthio)methylen)-3(2H)-benzofuranon-Derivaten
  作者：T. Gildenast、W. D�lling

  DOI：10.1007/bf00810773

  日期：1997.4

  3(Bis(alkylthio)methylene)-3H-isobenzofuran-1-ones 2a-e and 2-(bis(alkylthio)methylene)-3(2H)-benzofuranone derivatives 4a-c are obtained by reaction of phthalides 1a-d or 3(2H)-benzofuranone (coumaranone 3), respectively, with carbon disulfide under basic conditions followed by alkylation. The reaction behaviour of the new compounds 2 and 4 is investigated. 2-((2-Dimethylthio-1-oxo)ethyl)benzoic acid N,N-dimethylamide (7a) and 2-((2-dimethylthio-1-oxo)ethyl)-benzoic acid 2-methylpiperidide (7b) are surprisingly formed instead of the methylthio substitution products by treatment of 2a with the corresponding amine in the presence of aluminum chloride.

表征谱图