2-amino-7,7-dimethyl-4-(3-morpholino-4-nitro-5-(vinylthio)thien-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 1360687-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-amino-7,7-dimethyl-4-(3-morpholino-4-nitro-5-(vinylthio)thien-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(5-ethenylsulfanyl-3-morpholin-4-yl-4-nitrothiophen-2-yl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carbonitrile
• CAS: 1360687-38-2
• 化学式: C₂₂H₂₄N₄O₅S₂
• 分子量: 488.588
• InChiKey: SJTJSLTYCYRWAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-amino-7,7-dimethyl-4-(3-morpholino-4-nitro-5-(vinylthio)thien-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以30%的产率得到6,6-dimethyl-9-(3-morpholino-4-nitro-5-(vinylthio)thien-2-yl)-3-nitro-2-(vinylthio)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one
  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：

  2-chloro-3-morpholino-4-nitro-5-vinylsulfanylthiophene 在 吗啉 、 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 34.0h， 生成 2-amino-7,7-dimethyl-4-(3-morpholino-4-nitro-5-(vinylthio)thien-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  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