6-<(tert-butyldimethylsilyl)oxy>-3-methyl-4a,5,7,8,9,10,10a,10b-octahydro-1H-naphtho<1,2-c>pyran-1-one | 134678-36-7

• 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: 6-<(tert-butyldimethylsilyl)oxy>-3-methyl-4a,5,7,8,9,10,10a,10b-octahydro-1H-naphtho<1,2-c>pyran-1-one
• 英文别名: 6-[Tert-butyl(dimethyl)silyl]oxy-3-methyl-4a,5,7,8,9,10,10a,10b-octahydrobenzo[h]isochromen-1-one
• CAS: 134678-36-7
• 化学式: C₂₀H₃₂O₃Si
• 分子量: 348.558
• InChiKey: LFGVEUJJAIVOLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<(tert-butyldimethylsilyl)oxy>-3-methyl-4a,5,7,8,9,10,10a,10b-octahydro-1H-naphtho<1,2-c>pyran-1-one 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.0h， 以80%的产率得到4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-oxo-propyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
  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：

  6-甲基-吡喃-2-酮 、 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 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以60%的产率得到6-<(tert-butyldimethylsilyl)oxy>-3-methyl-4a,5,7,8,9,10,10a,10b-octahydro-1H-naphtho<1,2-c>pyran-1-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.