7-Allyloxy-6-hydroxy-cumarin | 66301-01-7

• 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: 7-Allyloxy-6-hydroxy-cumarin
• 英文别名: 6-Hydroxy-7-[(prop-2-en-1-yl)oxy]-2H-1-benzopyran-2-one；6-hydroxy-7-prop-2-enoxychromen-2-one
• CAS: 66301-01-7
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: GPFXZYJEMILRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Allyloxy-6-hydroxy-cumarin 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 215.0~225.0 ℃ 、133.32 Pa 条件下， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis and antifungal activity of coumarins and angular furanocoumarins

  摘要：

  Angelicin, a naturally occurring furanocoumarin, that showed antifungal activity, was considered as a lead structure for a group of synthetic coumarins. Antifungal activities of the synthesized coumarins and angelicin derivatives were reported against Candida albicans, Cryptococcus neoformans, Saccharomyces cerevisiae and Aspergillus niger. Human cell line cytotoxicity of several coumarins was evaluated against KB cells. Angelicin and several potent antifungals showed to be non-toxic in this assay.

  DOI：

  10.1016/s0968-0896(99)00138-8
• 作为产物：
  描述：

  秦皮甲素 在 硫酸 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 7-Allyloxy-6-hydroxy-cumarin
  参考文献：
  名称：

  Synthesis and antifungal activity of coumarins and angular furanocoumarins

  摘要：

  Angelicin, a naturally occurring furanocoumarin, that showed antifungal activity, was considered as a lead structure for a group of synthetic coumarins. Antifungal activities of the synthesized coumarins and angelicin derivatives were reported against Candida albicans, Cryptococcus neoformans, Saccharomyces cerevisiae and Aspergillus niger. Human cell line cytotoxicity of several coumarins was evaluated against KB cells. Angelicin and several potent antifungals showed to be non-toxic in this assay.

  DOI：

  10.1016/s0968-0896(99)00138-8

文献信息

• Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins
  作者：James A. Bull、Cristina Luján、Michael G. Hutchings、Peter Quayle

  DOI：10.1016/j.tetlet.2009.03.077

  日期：2009.7

  A new approach to the synthesis of the 6H-benzo[d]naphthal[,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. (C) 2009 Elsevier Ltd. All rights reserved.