5-amino-[11b]-hydro-1-methyl-3-phenylpyrazolo(3,4-b)thiohydropyrano(3,4-c)coumarin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-[11b]-hydro-1-methyl-3-phenylpyrazolo(3,4-b)thiohydropyrano(3,4-c)coumarin
• 英文别名: 11-Amino-16-methyl-14-phenyl-8-oxa-12-thia-14,15-diazatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,10,13(17),15-hexaen-9-one
• 化学式: C₂₀H₁₅N₃O₂S
• 分子量: 361.424
• InChiKey: SQWISFKKIGBKJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氧代-2H-苯并吡喃-3-硫代甲酰胺 、 依达拉奉 在 哌啶 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以73%的产率得到5-amino-[11b]-hydro-1-methyl-3-phenylpyrazolo(3,4-b)thiohydropyrano(3,4-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