6-chloro-4-cyano-7-methylcoumarin | 1112991-87-3

• 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: 6-chloro-4-cyano-7-methylcoumarin
• 英文别名: 6-Chloro-7-methyl-2-oxochromene-4-carbonitrile；6-chloro-7-methyl-2-oxochromene-4-carbonitrile
• CAS: 1112991-87-3
• 化学式: C₁₁H₆ClNO₂
• 分子量: 219.627
• InChiKey: MXCNXYIWLKGWDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-4-cyano-7-methylcoumarin 、 (E)-(buta-1,3-dien-1-yloxy)(tert-butyl)dimethylsilane 以 甲苯 为溶剂， 反应 0.5h， 生成 (+/-)-(6aS,10R,10aR)-2-chloro-10-(1,1-dimethylethyl)dimethylsilyloxy-3-methyl-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-10a-carbonitrile 、 (+/-)-(6aS,10S,10aR)-2-chloro-10-(1,1-dimethylethyl)dimethylsilyloxy-3-methyl-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-10a-carbonitrile
  参考文献：
  名称：

  Use of 4-Cyanocoumarins as Dienophiles in a Facile Synthesis of Highly Substituted Dibenzopyranones

  摘要：

  A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.

  DOI：

  10.1021/ol802792g
• 作为产物：
  描述：

  4-bromo-6-chloro-7-methylcoumarin 、 copper(l) cyanide 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6-chloro-4-cyano-7-methylcoumarin
  参考文献：
  名称：

  Use of 4-Cyanocoumarins as Dienophiles in a Facile Synthesis of Highly Substituted Dibenzopyranones

  摘要：

  A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.

  DOI：

  10.1021/ol802792g

文献信息

• Use of 4-Cyanocoumarins as Dienophiles in a Facile Synthesis of Highly Substituted Dibenzopyranones
  作者：Michael E. Jung、Damian A. Allen

  DOI：10.1021/ol802792g

  日期：2009.2.5

  A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.