4-amino-2-(3,3-diacetylmethylene)-N-phenyl-[10b]-hydro-2H-thiazino(5,4-c)coumarin | 291509-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 4-amino-2-(3,3-diacetylmethylene)-N-phenyl-[10b]-hydro-2H-thiazino(5,4-c)coumarin
• 英文别名: 3-(4-amino-5-oxo-1-phenyl-10bH-chromeno[4,3-d][1,3]thiazin-2-ylidene)pentane-2,4-dione
• CAS: 291509-10-9
• 化学式: C₂₂H₁₈N₂O₄S
• 分子量: 406.462
• InChiKey: YSMVOFXILRUEPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  89.7
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-环己基亚己基丙二腈 、 4-amino-2-(3,3-diacetylmethylene)-N-phenyl-[10b]-hydro-2H-thiazino(5,4-c)coumarin 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以46%的产率得到spiro-(4-amino-2,2-diacetyl-3-cyano-5,6,7,8-tetrahydronaphthyl)-1,2'-(4'-amino-10'b(H)-N-phenyl-1',3'-thiazino(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：

  2-氧代-2H-苯并吡喃-3-硫代甲酰胺 、 3-acetyl-4-methylthio-4-phenylaminobut-3-en-2-one 在 哌啶 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到4-amino-2-(3,3-diacetylmethylene)-N-phenyl-[10b]-hydro-2H-thiazino(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