12-<(tert-butyldimethylsilyl)oxy>-5H-benzonaphtho<2,1-d>pyran-5-one | 130043-16-2

• 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: 12-<(tert-butyldimethylsilyl)oxy>-5H-benzonaphtho<2,1-d>pyran-5-one
• 英文别名: 12-[tert-butyl(dimethyl)silyl]oxynaphtho[1,2-c]chromen-5-one
• CAS: 130043-16-2
• 化学式: C₂₃H₂₄O₃Si
• 分子量: 376.527
• InChiKey: JOMWNHHJGDMFOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  acetylcyclohexene tert-butyldimethylsilyl enol ether 在 2,6-二甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 8.5h， 生成 12-<(tert-butyldimethylsilyl)oxy>-5H-benzonaphtho<2,1-d>pyran-5-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

文献信息

• Diels-Alder reactions of 2-[(trialkylsilyl)oxy]pyrylium cations of 2H-pyran-2-one and 2H-1-benzopyran-2-one derivatives
  作者：Katsuo Ohkata、Yong Gyun Lee、Yukinori Utsumi、Kenji Ishimaru、Kinya Akiba

  DOI：10.1021/jo00017a014

  日期：1991.8

  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.