(2-Oxo-5-prop-2-enylchromen-6-yl) 2,2,2-trichloroacetate | 1171067-56-3

• 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: (2-Oxo-5-prop-2-enylchromen-6-yl) 2,2,2-trichloroacetate
• 英文别名: (2-oxo-5-prop-2-enylchromen-6-yl) 2,2,2-trichloroacetate
• CAS: 1171067-56-3
• 化学式: C₁₄H₉Cl₃O₄
• 分子量: 347.582
• InChiKey: KZSCNBLATSAXFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-Oxo-5-prop-2-enylchromen-6-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52%的产率得到C₁₃H₇ClO₂
  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：

  5-烯丙基-6-羟基-2H-色烯-2-酮 、 三氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到(2-Oxo-5-prop-2-enylchromen-6-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.