3-chloro-2-p-tolyl-4H-furo[3,2-c]chromen-4-one | 1033894-70-0

• 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: 3-chloro-2-p-tolyl-4H-furo[3,2-c]chromen-4-one
• 英文别名: 3-Chloro-2-(4-methylphenyl)furo[3,2-c]chromen-4-one
• CAS: 1033894-70-0
• 化学式: C₁₈H₁₁ClO₃
• 分子量: 310.737
• InChiKey: VEUZMIGWYZBKIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-2-p-tolyl-4H-furo[3,2-c]chromen-4-one 、 4-甲氧基苯硼酸 在 tris(dibenzylideneacetone)dipalladium (0) 三叔丁基膦 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以70%的产率得到3-(4-methoxyphenyl)-2-p-tolyl-4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Two Efficient Cascade Reactions to Synthesize Substituted Furocoumarins

  摘要：

  We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H2O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl2 as the oxidant afforded the 3-chloro2-substituted-4H-furo[3,2-c]chromen-4-one 3.

  DOI：

  10.1021/jo800439y
• 作为产物：
  描述：

  3-[2-(4-Methylphenyl)ethynyl]chromen-4-one 在 copper(I) bromide 、 copper dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以77%的产率得到3-chloro-2-p-tolyl-4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Two Efficient Cascade Reactions to Synthesize Substituted Furocoumarins

  摘要：

  We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H2O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl2 as the oxidant afforded the 3-chloro2-substituted-4H-furo[3,2-c]chromen-4-one 3.

  DOI：

  10.1021/jo800439y

文献信息

• A Novel Method for One-pot Synthesis of Furo[3,2-c]coumarin Derivatives from 4-Hydroxycoumarin and Arylglyoxal under Microwave Irradiation
  作者：Zhiwei Chen、Jianhao Bi、Weike Su

  DOI：10.1002/cjoc.201200157

  日期：2012.8

  A novel one‐pot synthesis of furo[3,2‐c]coumarins has been developed from readily available starting materials 4‐hydroxycoumarin and arylglyoxal. This method is simple, rapid and good yielding.

  从容易获得的起始原料4-羟基香豆素和芳基乙二醛开发了一种新颖的一锅合成呋喃[3,2- c ]香豆素。该方法简便，快速，收率高。