8-allyl-3-bromo-7-hydroxy-2H-chromen-2-one | 1171067-61-0

• 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: 8-allyl-3-bromo-7-hydroxy-2H-chromen-2-one
• CAS: 1171067-61-0
• 化学式: C₁₂H₉BrO₃
• 分子量: 281.106
• InChiKey: JWAFUDNYPMHBQK-UHFFFAOYSA-N

物化性质

• 沸点：
  448.0±45.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-allyl-3-bromo-7-hydroxy-2H-chromen-2-one 、 三氯乙酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以100%的产率得到(3-Bromo-2-oxo-8-prop-2-enylchromen-7-yl) 2,2,2-trichloroacetate
  参考文献：
  名称：

  Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.03.077
• 作为产物：
  描述：

  7-allyloxy-3-bromocoumarin 以 甲苯 为溶剂， 反应 6.0h， 生成 8-allyl-3-bromo-7-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.03.077