4-amino-2-(2,2-dicyanomethylene)-[10b]-hydro-2H-1,3-dithiano-(5,4-c)coumarin | 291509-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-amino-2-(2,2-dicyanomethylene)-[10b]-hydro-2H-1,3-dithiano-(5,4-c)coumarin
• 英文别名: 2-(4-amino-5-oxo-10bH-[1,3]dithiino[5,4-c]chromen-2-ylidene)propanedinitrile
• CAS: 291509-19-8
• 化学式: C₁₄H₇N₃O₂S₂
• 分子量: 313.36
• InChiKey: DBDIEISDRNEXHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.9
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  丙二腈 、 4-amino-2-(2,2-dicyanomethylene)-[10b]-hydro-2H-1,3-dithiano-(5,4-c)coumarin 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以61%的产率得到spiro (3-amino-2,2,4-tricyano-cyclob-2-enyl)-1,2'-(4'-amino-10'b(H)-N-phenyl-1',3'-dithiano(5,4-c)coumarin)
  参考文献：
  名称：

  NEW SYNTHETIC APPROACHES TO CONDENSED AND SPIRO COUMARINS: COUMARIN-3-THIOCARBOXAMIDE AS BUILDING BLOCK FOR THE SYNTHESIS OF CONDENSED AND SPIRO COUMARINS

  摘要：

  Coumarin-3-thiocarboxamide 1 was reacted with malononitrile, cyanoacetamide or cyanothioacetamide to give the corresponding thiopyrano(3,4-c)coumarin-1-carbonitrile 2. Also, compound 1 was reacted with a variety of active methylenes having an alpha-cyano or alpha-keto group to give thiopyranocoumarin derivatives 3-9. The reaction of compound 1 with different ketene N,S-acetals, afforded the corresponding thiazino(5,4c)coumarin derivatives 10,13 and 16. On reacting compound 10 or 13 with malononitrile, spiro pyran-4,2'-thiazino(5,4-c)coumarin 11 or 14 were obtained, while the reaction of compound 16 with malononitrile gave spiro cyclobutene-1,2'-thiazino(5,4-c)coumarin derivative 17. Treating of compounds 10, 13 or 16 with cyclohexylidenemalononitrile afforded spiro naphthyl-1,2'-tkiazino(5,4-c) coumarin derivatives 12,15 or 18 respectively. Treatment of compound I with CS2 and malononitrile under PTC condition afforded 1,3-dithiano(5,4-c) coumarin derivative 19, which in turn reacted with malononitrile or cyclohexylidenemalononitrile to afford spiro cyclobut-2-enyl-1,2'-(1,3)dithiano(5,4-c)coumarin 20 and spiro naphthyl-1,'2-(1,3)dithiano(5,4-c)coumarin 21 derivatives, respectively.

  DOI：

  10.1080/10426500008043675
• 作为产物：
  描述：

  二硫化碳 、 2-氧代-2H-苯并吡喃-3-硫代甲酰胺 、 丙二腈 在 叔丁胺氢溴酸盐 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到4-amino-2-(2,2-dicyanomethylene)-[10b]-hydro-2H-1,3-dithiano-(5,4-c)coumarin
  参考文献：
  名称：

  NEW SYNTHETIC APPROACHES TO CONDENSED AND SPIRO COUMARINS: COUMARIN-3-THIOCARBOXAMIDE AS BUILDING BLOCK FOR THE SYNTHESIS OF CONDENSED AND SPIRO COUMARINS

  摘要：

  Coumarin-3-thiocarboxamide 1 was reacted with malononitrile, cyanoacetamide or cyanothioacetamide to give the corresponding thiopyrano(3,4-c)coumarin-1-carbonitrile 2. Also, compound 1 was reacted with a variety of active methylenes having an alpha-cyano or alpha-keto group to give thiopyranocoumarin derivatives 3-9. The reaction of compound 1 with different ketene N,S-acetals, afforded the corresponding thiazino(5,4c)coumarin derivatives 10,13 and 16. On reacting compound 10 or 13 with malononitrile, spiro pyran-4,2'-thiazino(5,4-c)coumarin 11 or 14 were obtained, while the reaction of compound 16 with malononitrile gave spiro cyclobutene-1,2'-thiazino(5,4-c)coumarin derivative 17. Treating of compounds 10, 13 or 16 with cyclohexylidenemalononitrile afforded spiro naphthyl-1,2'-tkiazino(5,4-c) coumarin derivatives 12,15 or 18 respectively. Treatment of compound I with CS2 and malononitrile under PTC condition afforded 1,3-dithiano(5,4-c) coumarin derivative 19, which in turn reacted with malononitrile or cyclohexylidenemalononitrile to afford spiro cyclobut-2-enyl-1,2'-(1,3)dithiano(5,4-c)coumarin 20 and spiro naphthyl-1,'2-(1,3)dithiano(5,4-c)coumarin 21 derivatives, respectively.

  DOI：

  10.1080/10426500008043675