5-cyclohex-2-enyl-6-hydroxycoumarin | 213664-96-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-cyclohex-2-enyl-6-hydroxycoumarin
• 英文别名: 5-Cyclohex-2-en-1-yl-6-hydroxychromen-2-one
• CAS: 213664-96-1
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: PLESVLSKBPFECU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-cyclohex-2-enyl-6-hydroxycoumarin 在 hexamethylene tetramine hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到2-bromo-1,3-propano-1,2,3-trihydropyrano[3,2-f]benzopyran-8-one
  参考文献：
  名称：

  Synthesis of Bioactive Polyheterocycles: Regioselective Cyclisation of 5-Cyclohex-2-Enyl-6-Hydroxy[1]Benzopyran-2-One

  摘要：

  5-Cyclohex-2-enyl-6-hydroxycoumarin (4) was synthesised in 80 % yield alongwith 4% of 7-cyclohex-2-enyl-6-hydroxycoumarin (5) by the thermal sigmatropic rearrangement of 6-cyclohex-2-enyloxycoumarin (3) in refluxing N,N-diethylaniline. Treatment of 4 with m-chloroperoxybenzoic acid in refluxing benzene for 4 h gave 8-hydroxy-7a,8,9,10,11,11a-hexahydrobenzofuro[3,2- f]benzopyran-3-one (6) in 90 % yield which was then dehydrogenated to benzofuro[3,2-f]benzopyran-3-one (7) with excess of DDQ. Compound 4 was also cyclised with pyridine hydrotribromide or hexamine hydrotribromide to 2-bromo-1,3-propano-1,2,3-trihydropyrano[3,2-f]benzopyran-8-one (8) in 88 % or 95 % yield respectively. Compound 4 when treated with cold cone. H2SO4 at 0-5 degrees C for 4 h furnished the cyclised 1,3-propano-1,2,3-trihydropyrano[3,2-f]benzopyran-8-one (10) in 90 % yield.

  DOI：

  10.1080/00397919808004910
• 作为产物：
  描述：

  6-羟基香豆素 在 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 5-cyclohex-2-enyl-6-hydroxycoumarin
  参考文献：
  名称：

  Synthesis of Bioactive Polyheterocycles: Regioselective Cyclisation of 5-Cyclohex-2-Enyl-6-Hydroxy[1]Benzopyran-2-One

  摘要：

  5-Cyclohex-2-enyl-6-hydroxycoumarin (4) was synthesised in 80 % yield alongwith 4% of 7-cyclohex-2-enyl-6-hydroxycoumarin (5) by the thermal sigmatropic rearrangement of 6-cyclohex-2-enyloxycoumarin (3) in refluxing N,N-diethylaniline. Treatment of 4 with m-chloroperoxybenzoic acid in refluxing benzene for 4 h gave 8-hydroxy-7a,8,9,10,11,11a-hexahydrobenzofuro[3,2- f]benzopyran-3-one (6) in 90 % yield which was then dehydrogenated to benzofuro[3,2-f]benzopyran-3-one (7) with excess of DDQ. Compound 4 was also cyclised with pyridine hydrotribromide or hexamine hydrotribromide to 2-bromo-1,3-propano-1,2,3-trihydropyrano[3,2-f]benzopyran-8-one (8) in 88 % or 95 % yield respectively. Compound 4 when treated with cold cone. H2SO4 at 0-5 degrees C for 4 h furnished the cyclised 1,3-propano-1,2,3-trihydropyrano[3,2-f]benzopyran-8-one (10) in 90 % yield.

  DOI：

  10.1080/00397919808004910

文献信息

• Synthesis of Bioactive Polyheterocycles: Regioselective Cyclisation of 5-Cyclohex-2-Enyl-6-Hydroxy[1]Benzopyran-2-One
  作者：Krishna C. Majumdar、Pranab Chatterjee

  DOI：10.1080/00397919808004910

  日期：1998.10

  5-Cyclohex-2-enyl-6-hydroxycoumarin (4) was synthesised in 80 % yield alongwith 4% of 7-cyclohex-2-enyl-6-hydroxycoumarin (5) by the thermal sigmatropic rearrangement of 6-cyclohex-2-enyloxycoumarin (3) in refluxing N,N-diethylaniline. Treatment of 4 with m-chloroperoxybenzoic acid in refluxing benzene for 4 h gave 8-hydroxy-7a,8,9,10,11,11a-hexahydrobenzofuro[3,2- f]benzopyran-3-one (6) in 90 % yield which was then dehydrogenated to benzofuro[3,2-f]benzopyran-3-one (7) with excess of DDQ. Compound 4 was also cyclised with pyridine hydrotribromide or hexamine hydrotribromide to 2-bromo-1,3-propano-1,2,3-trihydropyrano[3,2-f]benzopyran-8-one (8) in 88 % or 95 % yield respectively. Compound 4 when treated with cold cone. H2SO4 at 0-5 degrees C for 4 h furnished the cyclised 1,3-propano-1,2,3-trihydropyrano[3,2-f]benzopyran-8-one (10) in 90 % yield.