(+/-)-(6aS,10R,10aR)-10-(1,1-dimethylethyl)dimethylsilyloxy-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-10a-carbonitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: (+/-)-(6aS,10R,10aR)-10-(1,1-dimethylethyl)dimethylsilyloxy-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-10a-carbonitrile
• 英文别名: (6aS,10R,10aR)-10-[tert-butyl(dimethyl)silyl]oxy-6-oxo-7,10-dihydro-6aH-benzo[c]chromene-10a-carbonitrile
• 化学式: C₂₀H₂₅NO₃Si
• 分子量: 355.509
• InChiKey: AIJCZNZJPKLFNM-MDYRTPRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-(6aS,10R,10aR)-10-(1,1-dimethylethyl)dimethylsilyloxy-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-10a-carbonitrile 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以92%的产率得到苯并[c]苯并吡喃-6-酮
  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：

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

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.