5-[1-Tri(propan-2-yl)silylpyrrol-3-yl]oxolan-2-one | 1026802-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-[1-Tri(propan-2-yl)silylpyrrol-3-yl]oxolan-2-one
• CAS: 1026802-86-7
• 化学式: C₁₇H₂₉NO₂Si
• 分子量: 307.508
• InChiKey: FDIMNGCWFTZMOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[1-Tri(propan-2-yl)silylpyrrol-3-yl]oxolan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以99%的产率得到4-<1-(Triisopropylsilyl)pyrrol-3-yl>butyric acid
  参考文献：
  名称：

  Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions

  摘要：

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.

  DOI：

  10.1021/jo00100a039
• 作为产物：
  描述：

  1-(三异丙基甲硅烷基)吡咯 在 sodium tetrahydroborate 、 三氯化铝 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 14.08h， 生成 5-[1-Tri(propan-2-yl)silylpyrrol-3-yl]oxolan-2-one
  参考文献：
  名称：

  Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions

  摘要：

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.

  DOI：

  10.1021/jo00100a039

文献信息

• Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+, J. Org. Chem, 59 (1994) N 21, S 6322-6337
  作者：Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+

  DOI：——

  日期：——
• Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions
  作者：Steven R. Angle、Damian O. Arnaiz、James P. Boyce、Rogelio P. Frutos、Michael S. Louie、Heather L. Mattson-Arnaiz、Jon D. Rainier、Kenneth D. Turnbull、Wenjin Yang

  DOI：10.1021/jo00100a039

  日期：1994.10

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.