(6-Methoxy-2-oxo-8-prop-2-enylchromen-7-yl) 2,2,2-trichloroacetate | 1171067-69-8

• 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: (6-Methoxy-2-oxo-8-prop-2-enylchromen-7-yl) 2,2,2-trichloroacetate
• 英文别名: (6-methoxy-2-oxo-8-prop-2-enylchromen-7-yl) 2,2,2-trichloroacetate
• CAS: 1171067-69-8
• 化学式: C₁₅H₁₁Cl₃O₅
• 分子量: 377.608
• InChiKey: WPLWVGQXBJAFHF-UHFFFAOYSA-N

物化性质

• 沸点：
  460.8±45.0 °C(predicted)
• 密度：
  1.467±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6-Methoxy-2-oxo-8-prop-2-enylchromen-7-yl) 2,2,2-trichloroacetate 在 copper(l) chloride 、 1,3-di(2-picolyl)imidazolium chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以84%的产率得到C₁₄H₉ClO₃
  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：

  三氯乙酰氯 、 8-allylscopoletin 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(6-Methoxy-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

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.