methyl 6,8-dichloro-2-oxo-2H-chromene-4-carboxylate

• 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: methyl 6,8-dichloro-2-oxo-2H-chromene-4-carboxylate
• 英文别名: methyl-6,8-dichloro-2-oxo-2H-chromene-4-carboxylate；Methyl 6,8-dichloro-2-oxochromene-4-carboxylate
• 化学式: C₁₁H₆Cl₂O₄
• 分子量: 273.072
• InChiKey: LGDPVCHBCXZOAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁炔二酸二甲酯 、 2,4-二氯酚 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以90%的产率得到methyl 6,8-dichloro-2-oxo-2H-chromene-4-carboxylate
  参考文献：
  名称：

  Novel Synthesis of Oxygenated Coumarins from Substituted Phenols Mediated by Vinyl Triphenylphosphonium Salt Under Microwave Irradiation

  摘要：

  Protonation of the highly reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate(DMAD) by substituted phenols lead to vinyl triphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with a phenolate conjugate base to produce. 4-carboxymethyl coumarins in fairly highly yields.

  DOI：

  10.1080/10426500214882

文献信息

• A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt
  作者：Issa Yavari、Rahim Hekmat-Shoar、Afsaneh Zonouzi

  DOI：10.1016/s0040-4039(98)00206-8

  日期：1998.4

  Protonation of the reactive 1:1 intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by substituted phenols leads to a vinyltriphenylphosphonium salt, which undergoes aromatic electrophilic substitution reaction with the phenolate conjugate base to produce 4-carboxymethylcoumarins in fairly high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• TRIPHENYPHOSPHINE-MEDIATED EFFICIENT SYNTHESIS OF FUNCTIONALIZED 2-OXO-2<i>H</i>-CHROMENES
  作者：Issa Yavari、Rahebeh Amiri、Mina Haghdadi

  DOI：10.1080/10426500490474798

  日期：2004.11.1

  Dimethyl acetylenedicarboxylate reacts smoothly with phenol derivatives, such as 4-chloro-3,5-dimethylphenol, 2-chloro-5-methylphenol, 4-chloro-2-methylphenol, 2,4-dichlorophenol, or 2-bromophenol in the presence of triphenylphosphine to produce highly functionalized 2-oxo-2H-chromeus (counarins) in moderate yields.