N-甲氧基-N-甲基-4-<1-(三异丙基甲硅烷基)-3-吡咯基>丁酰胺 | 1027542-87-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: N-甲氧基-N-甲基-4-<1-(三异丙基甲硅烷基)-3-吡咯基>丁酰胺
• 英文名称: N-Methoxy-N-methyl-4-<1-(triisopropylsilyl)-3-pyrrolyl>butanamide
• 英文别名: N-methoxy-N-methyl-4-[1-tri(propan-2-yl)silylpyrrol-3-yl]butanamide
• CAS: 1027542-87-5
• 化学式: C₁₉H₃₆N₂O₂Si
• 分子量: 352.593
• InChiKey: OKOPPZPUQLQWEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲氧基-N-甲基-4-<1-(三异丙基甲硅烷基)-3-吡咯基>丁酰胺 在 palladium on activated charcoal 正丁基锂 、 氢气 、 叔丁基锂 、 silver(l) oxide 作用下， 以 乙醚 、 氘代氯仿 为溶剂， -78.0~25.0 ℃ 、365.42 kPa 条件下， 反应 21.33h， 生成 2,6-Dimethyl-4-<4-<1-(triisopropylsilyl)pyrrol-3-yl>butylidene>-2,5-cyclohexadien-1-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
• 作为产物：
  描述：

  1-(三异丙基甲硅烷基)吡咯 在 palladium on activated charcoal sodium tetrahydroborate 、 三氯化铝 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 25.0 ℃ 、365.42 kPa 条件下， 反应 32.58h， 生成 N-甲氧基-N-甲基-4-<1-(三异丙基甲硅烷基)-3-吡咯基>丁酰胺
  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

• A stereoselective formal synthesis of (±)-(γ)-lycorane
  作者：Steven R. Angle、Jim P. Boyce

  DOI：10.1016/0040-4039(95)01245-d

  日期：1995.8

  Compound 11, a common intermediate in several syntheses of (+/-)-gamma-lycorane, was prepared, from commercially available N-triisopropylsilyl pyrrole, in 13 steps and overall 34% yield. The key step of the synthesis involved the diastereoselective hydrogenation of a substituted pyrrole ring.
• 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.