10-<(tert-butyldimethylsilyl)oxy>-3b-(ethoxycarbonyl)-2,3,3a,3b,4,6,7,8,8b,9-decahydro-1H-cyclopentindeno<5,4-d>pyran-4-one | 134627-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 10-<(tert-butyldimethylsilyl)oxy>-3b-(ethoxycarbonyl)-2,3,3a,3b,4,6,7,8,8b,9-decahydro-1H-cyclopentindeno<5,4-d>pyran-4-one
• 英文别名: 10-[(tert-butyldimethylsilyl)oxy]-3b-(ethoxycarbonyl)-2,3,3a,3b,4,6,7,8,8b,9-decahydro-1H-cyclopent[b]indeno[5,4-d]pyran-4-one；Ethyl 15-[tert-butyl(dimethyl)silyl]oxy-8-oxo-7-oxatetracyclo[7.7.0.02,6.010,14]hexadeca-2(6),14-diene-9-carboxylate
• CAS: 134627-04-6
• 化学式: C₂₄H₃₆O₅Si
• 分子量: 432.632
• InChiKey: AMPZHGVVFJGSIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-乙酰基-1-环戊烯 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 21.0h， 生成 10-<(tert-butyldimethylsilyl)oxy>-3b-(ethoxycarbonyl)-2,3,3a,3b,4,6,7,8,8b,9-decahydro-1H-cyclopentindeno<5,4-d>pyran-4-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.