(E)-1,1-bis(methylthio)-3-nitro-4-(2-thienyl)-1,3-butadiene | 467421-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-1,1-bis(methylthio)-3-nitro-4-(2-thienyl)-1,3-butadiene
• 英文别名: 2-[(1E)-4,4-bis(methylsulfanyl)-2-nitrobuta-1,3-dienyl]thiophene
• CAS: 467421-96-1
• 化学式: C₁₀H₁₁NO₂S₃
• 分子量: 273.401
• InChiKey: ABGOSEUUVJIPGR-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1,1-bis(methylthio)-3-nitro-4-(2-thienyl)-1,3-butadiene 在 lead 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到3-hydroxyimino-1,1-bis(methylthio)-4-(2-thienyl)-1-butene
  参考文献：
  名称：

  Access to 3-arylmethyl-5-(methylthio)isoxazoles via an initial ring-opening of 2-methylthio-4-nitrothiophene

  摘要：

  The reactions of 1, 1 -bis(methylthio)-3-nitro-4-pyrrolidino-1.3-butadiene (deriving from the initial ring-opening of 2-methylthio-4-nitrothiophene with pyrrolidine and silver nitrate in EtOH) with arylmagnesium bromides result in the chemoselective replacement of the pyrrolidino group with the aryl moiety of the Grignards. The 4-aryl-1,1-bis(methylthio)-3-nitro-1,3-butadienes thus obtained are the key intermediates for the effective synthesis, through the corresponding reduction products 4-aryl-3-hydroximino-1, 1-bis(methylthio)-1-butenes, of the previously unknown 3-arylmethyl-5-(methylthio)isoxazoles. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00292-2
• 作为产物：
  描述：

  magnesium,2H-thiophen-2-ide,bromide 、 (1E)-4,4-bis(methylthio)-2-nitro-1-pyrrolidino-1,3-butadiene 以 四氢呋喃 为溶剂， 以88%的产率得到(E)-1,1-bis(methylthio)-3-nitro-4-(2-thienyl)-1,3-butadiene
  参考文献：
  名称：

  Access to 3-arylmethyl-5-(methylthio)isoxazoles via an initial ring-opening of 2-methylthio-4-nitrothiophene

  摘要：

  The reactions of 1, 1 -bis(methylthio)-3-nitro-4-pyrrolidino-1.3-butadiene (deriving from the initial ring-opening of 2-methylthio-4-nitrothiophene with pyrrolidine and silver nitrate in EtOH) with arylmagnesium bromides result in the chemoselective replacement of the pyrrolidino group with the aryl moiety of the Grignards. The 4-aryl-1,1-bis(methylthio)-3-nitro-1,3-butadienes thus obtained are the key intermediates for the effective synthesis, through the corresponding reduction products 4-aryl-3-hydroximino-1, 1-bis(methylthio)-1-butenes, of the previously unknown 3-arylmethyl-5-(methylthio)isoxazoles. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00292-2