4-chloro-7-methoxy-3-(4-methoxyphenyl)coumarin | 138616-98-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4-chloro-7-methoxy-3-(4-methoxyphenyl)coumarin
• 英文别名: 4-Chloro-7-methoxy-3-(4-methoxyphenyl)-coumarin；4-chloro-7-methoxy-3-(4-methoxyphenyl)chromen-2-one
• CAS: 138616-98-5
• 化学式: C₁₇H₁₃ClO₄
• 分子量: 316.741
• InChiKey: QISCGHUUPZKMCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-7-methoxy-3-(4-methoxyphenyl)coumarin 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.67h， 生成 3,9-dimethoxy-11H-<1>benzopyrano<4,3-b>indol-6-one
  参考文献：
  名称：

  Potential non-steroidal estrogens and antiestrogens, IV Organic azides in heterocyclic synthesis, part 13: Synthesis of aza- and diazacoumestrols via azido derivatives

  摘要：

  4-Chloro-3-aryl-coumarins and quinolones 2 a-e undergo thermolytic ring closure by reaction with sodium azide in refluxing dimethyl formamide to yield indolo[3,2-c]coumarins and indolo[3,2-c]quinolin-6(5H)-ones 6 a-e. In the case of the coumarin 2 a the azido coumarin 5 can be isolated. The mono- and diazacoumestrol-dimethylethers 6 a-c are converted into the coumestrol analogues 7 a-c and their diacetyl derivatives 8 a-c.

  DOI：

  10.1007/bf00815924
• 作为产物：
  描述：

  4-hydroxy-7-methoxy-3-(4-methoxyphenyl)coumarin 在 三氯氧磷 作用下， 反应 1.5h， 以68%的产率得到4-chloro-7-methoxy-3-(4-methoxyphenyl)coumarin
  参考文献：
  名称：

  Potential non-steroidal estrogens and antiestrogens, IV Organic azides in heterocyclic synthesis, part 13: Synthesis of aza- and diazacoumestrols via azido derivatives

  摘要：

  4-Chloro-3-aryl-coumarins and quinolones 2 a-e undergo thermolytic ring closure by reaction with sodium azide in refluxing dimethyl formamide to yield indolo[3,2-c]coumarins and indolo[3,2-c]quinolin-6(5H)-ones 6 a-e. In the case of the coumarin 2 a the azido coumarin 5 can be isolated. The mono- and diazacoumestrol-dimethylethers 6 a-c are converted into the coumestrol analogues 7 a-c and their diacetyl derivatives 8 a-c.

  DOI：

  10.1007/bf00815924

文献信息

• Potential non-steroidal estrogens and antiestrogens, IV Organic azides in heterocyclic synthesis, part 13: Synthesis of aza- and diazacoumestrols via azido derivatives
  作者：Wolfgang Stadlbauer、Rita Laschober、Thomas Kappe

  DOI：10.1007/bf00815924

  日期：1991.10

  4-Chloro-3-aryl-coumarins and quinolones 2 a-e undergo thermolytic ring closure by reaction with sodium azide in refluxing dimethyl formamide to yield indolo[3,2-c]coumarins and indolo[3,2-c]quinolin-6(5H)-ones 6 a-e. In the case of the coumarin 2 a the azido coumarin 5 can be isolated. The mono- and diazacoumestrol-dimethylethers 6 a-c are converted into the coumestrol analogues 7 a-c and their diacetyl derivatives 8 a-c.