5-Methoxy-4-methyl-2H-[1]benzofuro[2,3-h][1]benzopyran-2-one | 195320-26-4

• 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-Methoxy-4-methyl-2H-[1]benzofuro[2,3-h][1]benzopyran-2-one
• 英文别名: 5-methoxy-4-methyl-[1]benzofuro[2,3-h]chromen-2-one
• CAS: 195320-26-4
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: PKIHKVFVONFMCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Methoxy-4-methyl-2H-[1]benzofuro[2,3-h][1]benzopyran-2-one 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 4.0h， 生成 5-Hydroxy-4-methyl-[1]benzofuro[2,3-h]chromen-2-one
  参考文献：
  名称：

  A new benzoangelicin with strong photobiological activity

  摘要：

  Benzoangelicins 4-6 were synthesized in good yields from 7-hydroxy-5-methoxy-4-methylcoumarin (1). In the absence of UVA radiation, compounds 5 and 6 were only weakly active against HL60 and HeLa tumour cells; in its presence, compound 6 was 10 times more active than the reference compound 8-methoxypsoralen. None of 4-6 exhibited cutaneous phototoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00640-x
• 作为产物：
  描述：

  2-氯环己酮 在 sodium hydroxide 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 、 苯 为溶剂， 生成 5-Methoxy-4-methyl-2H-[1]benzofuro[2,3-h][1]benzopyran-2-one
  参考文献：
  名称：

  A new benzoangelicin with strong photobiological activity

  摘要：

  Benzoangelicins 4-6 were synthesized in good yields from 7-hydroxy-5-methoxy-4-methylcoumarin (1). In the absence of UVA radiation, compounds 5 and 6 were only weakly active against HL60 and HeLa tumour cells; in its presence, compound 6 was 10 times more active than the reference compound 8-methoxypsoralen. None of 4-6 exhibited cutaneous phototoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00640-x

文献信息

• Synthesis of Linear and Angular Benzofurocoumarins
  作者：Carmen Terán、Rocio Miranda、Lourdes Santana、Marta Teijeira、Eugenio Uriarte

  DOI：10.1055/s-1997-1381

  日期：1997.12

  A four-step synthetic approach to substituted linear and angular benzofurocoumarins is described. Starting from 5-methoxyresorcinol, this approach afforded good yields of benzopsoralen (7), benzoangelicine (8), and benzoallopsoralen (11), which bear easily hydrolysed methoxy groups and thus allow access to other substituted compounds with potential as photochemotherapeutic agents.

  描述了取代的线性和有角苯并呋喃香豆素的四步合成方法。从 5-甲氧基间苯二酚开始，这种方法获得了苯并补骨脂素 (7)、苯并当归素 (8) 和苯并别补骨脂素 (11) 的良好产率，它们带有容易水解的甲氧基，因此可以得到其他有潜力作为光化疗剂的取代化合物。