ethyl 4-(2-(2,2-dicyanovinyl)-4-nitro-5-(vinylthio)thien-3-yl)piperazine-1-carboxylate | 1449017-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 4-(2-(2,2-dicyanovinyl)-4-nitro-5-(vinylthio)thien-3-yl)piperazine-1-carboxylate
• 英文别名: Ethyl 4-[2-(2,2-dicyanoethenyl)-5-ethenylsulfanyl-4-nitrothiophen-3-yl]piperazine-1-carboxylate；ethyl 4-[2-(2,2-dicyanoethenyl)-5-ethenylsulfanyl-4-nitrothiophen-3-yl]piperazine-1-carboxylate
• CAS: 1449017-64-4
• 化学式: C₁₇H₁₇N₅O₄S₂
• 分子量: 419.485
• InChiKey: YTQINGNSRMRWGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  180
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 4-(2-(2,2-dicyanovinyl)-4-nitro-5-(vinylthio)thien-3-yl)piperazine-1-carboxylate 、 5,5-二甲基-1,3-环己二酮 在 吗啉 作用下， 以 乙醇 为溶剂， 反应 11.0h， 以75%的产率得到ethyl 4-(2-(2-amino-3-cyano-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromen-4-yl)-4-nitro-5-(vinylthio)thien-3-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones

  摘要：

  Knoevenagel condensation of 3,4-push-pull-substituted thiophene-2-carbaldehydes 4 with malononitrile gives the gem-dicyanovinylthiophenes 5, followed by a Michael addition of dimedone and a subsequent cyclization to 4-(2-thienyl)-5,6,7,8-tetrahydro-4H-chromen-5-ones 6. Protonolysis of the latter in methanol led to a mixture of four heterocycles 7-10, the main product being the novel tricyclic 9-(2-thienyl)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one derivative 7. A mechanism of the protonolysis reaction is proposed, the structures of the two products 7a/8a have been confirmed by X-ray analysis.

  DOI：

  10.3987/com-12-s(n)108
• 作为产物：
  描述：

  ethyl 4-(2-chloro-4-nitro-5-(vinylsulfanyl)-3-thienyl)-1-piperazinecarboxylate 在 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 ethyl 4-(2-(2,2-dicyanovinyl)-4-nitro-5-(vinylthio)thien-3-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones

  摘要：

  Knoevenagel condensation of 3,4-push-pull-substituted thiophene-2-carbaldehydes 4 with malononitrile gives the gem-dicyanovinylthiophenes 5, followed by a Michael addition of dimedone and a subsequent cyclization to 4-(2-thienyl)-5,6,7,8-tetrahydro-4H-chromen-5-ones 6. Protonolysis of the latter in methanol led to a mixture of four heterocycles 7-10, the main product being the novel tricyclic 9-(2-thienyl)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one derivative 7. A mechanism of the protonolysis reaction is proposed, the structures of the two products 7a/8a have been confirmed by X-ray analysis.

  DOI：

  10.3987/com-12-s(n)108