methyl 3-(5-chloro-2-hydroxyphenyl)propiolate | 1241956-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 3-(5-chloro-2-hydroxyphenyl)propiolate
• 英文别名: Methyl 3-(5-chloro-2-hydroxyphenyl)prop-2-ynoate
• CAS: 1241956-38-6
• 化学式: C₁₀H₇ClO₃
• 分子量: 210.617
• InChiKey: VJEFRCUGJTVPSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(5-chloro-2-hydroxyphenyl)propiolate 在 碘 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以60%的产率得到6-chloro-3,4-diiodo-2H-chromen-2-one
  参考文献：
  名称：

  Condition-controlled selective synthesis of coumarins and flavones from 3-(2-hydroxyphenyl)propiolates and iodine

  摘要：

  2H-Chromen-2-ones (coumarins) and 4H-chromen-4-ones (flavones) were selectively prepared via the reaction of 3-(2-hydroxyphenyl)propiolates with iodine in toluene and N,N-dimethylformide, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.150

文献信息

• One-pot synthesis of 2-aryl-3-alkoxycarbonyl chromones through a cascade Lewis acid-catalyzed aldehyde olefination/oxa-Michael addition/oxidation
  作者：Ningning Wang、Shuying Cai、Chao Zhou、Ping Lu、Yanguang Wang

  DOI：10.1016/j.tet.2012.11.008

  日期：2013.1

  were effectively constructed from aryl aldehydes and 3-(2-(methoxymethoxy)phenyl)propiolates via a cascade Lewis acid catalyzed phenol ether deprotection/aldehyde olefination/intramolecular oxa-Michael addition reaction, and a sequential oxidation. This four-step reaction could be conducted in one-pot with high atom efficiency.

  通过级联路易斯酸催化的酚醚脱保护/醛烯化/分子内氧杂-迈克尔加成反应和顺序氧化反应，由芳基醛和3-（2-（甲氧基甲氧基）苯基）丙酸酯有效地构建了2-芳基-3-烷氧基羰基色酮。该四步反应可以在一个锅中以高原子效率进行。
• Copper-Catalyzed Three-Component Synthesis of 2-Iminodihydrocoumarins and 2-Iminocoumarins
  作者：Yang Shen、Sunliang Cui、Jing Wang、Xiaopeng Chen、Ping Lu、Yanguang Wang

  DOI：10.1002/adsc.200900890

  日期：——

  AbstractAn efficient synthesis of N‐sulfonyl‐substituted 2‐imino‐3,4‐dihydrocoumarins and 2‐iminocoumarins via a copper‐catalyzed multicomponent reaction of sulfonyl azides with terminal alkynes and β‐(ortho‐hydroxyphenyl)‐α,β‐unsaturated ketones or ortho‐hydroxyphenylpropiolates has been developed. The cascade process involves trapping the keteimine by a nucleophilic addition and an intramolecular Michael addition. This methodology could well be extended to the concise synthesis of the polysubstituted piperidine scaffold.