9-<(tert-butyldimethylsilyl)oxy>-7-phenyl-6a,7,10,10a-tetrahydro-6H-dibenzopyran-6-one | 134593-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 9-<(tert-butyldimethylsilyl)oxy>-7-phenyl-6a,7,10,10a-tetrahydro-6H-dibenzopyran-6-one
• CAS: 134593-97-8
• 化学式: C₂₅H₃₀O₃Si
• 分子量: 406.597
• InChiKey: BOEPOLMFXSVXDI-QZNHQXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-<(tert-butyldimethylsilyl)oxy>-7-phenyl-6a,7,10,10a-tetrahydro-6H-dibenzopyran-6-one 在 三甲基氯硅烷 、 lithium diisopropyl amide 作用下， 生成 9-<(tert-butyldimethylsilyl)oxy>-7-phenyl-6a,7,10,10a-tetrahydro-6H-dibenzopyran-6-one
  参考文献：
  名称：

  Diels-Alder reactions of 2-[(trialkylsilyl)oxy]pyrylium cations of 2H-pyran-2-one and 2H-1-benzopyran-2-one derivatives

  摘要：

  The reactions of 6-methyl-2H-pyran-2-one and 2H-1-benzopyran-2-one with the 2-(trialkylsilyl)oxy dienes 6a-d in the presence of tert-butyldimethylsilyl triflate gave the [4 + 2] cycloadducts 7a-c and 8a-d regio- and stereoselectively in moderate yields. The ring junction in the cycloadducts is cis. The stereochemistry of 8a-d is discussed in terms of the H-1 NMR spectra of the compounds. Similar reactions of 3-(ethoxycarbonyl)-2-pyrones and 3-(alkoxycarbonyl)coumarins with the 2-(trialkylsilyl)oxy dienes 6a-e gave the cycloadducts 14-18 in satisfactory yields. Dehydrogenation of 7c, 8b, and 8c with DDQ in refluxing toluene afforded 23-25, respectively.

  DOI：

  10.1021/jo00017a014
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 2,6-二甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 lithium diisopropyl amide 作用下， 反应 9.5h， 生成 9-<(tert-butyldimethylsilyl)oxy>-7-phenyl-6a,7,10,10a-tetrahydro-6H-dibenzopyran-6-one
  参考文献：
  名称：

  Diels-Alder reactions of 2-[(trialkylsilyl)oxy]pyrylium cations of 2H-pyran-2-one and 2H-1-benzopyran-2-one derivatives

  摘要：

  The reactions of 6-methyl-2H-pyran-2-one and 2H-1-benzopyran-2-one with the 2-(trialkylsilyl)oxy dienes 6a-d in the presence of tert-butyldimethylsilyl triflate gave the [4 + 2] cycloadducts 7a-c and 8a-d regio- and stereoselectively in moderate yields. The ring junction in the cycloadducts is cis. The stereochemistry of 8a-d is discussed in terms of the H-1 NMR spectra of the compounds. Similar reactions of 3-(ethoxycarbonyl)-2-pyrones and 3-(alkoxycarbonyl)coumarins with the 2-(trialkylsilyl)oxy dienes 6a-e gave the cycloadducts 14-18 in satisfactory yields. Dehydrogenation of 7c, 8b, and 8c with DDQ in refluxing toluene afforded 23-25, respectively.

  DOI：

  10.1021/jo00017a014