N-(N'-tert-butylformimidoyl)-2-(trimethylsilyl)-4-tert-butylpiperidine | 133165-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: N-(N'-tert-butylformimidoyl)-2-(trimethylsilyl)-4-tert-butylpiperidine
• CAS: 133165-16-9
• 化学式: C₁₇H₃₆N₂Si
• 分子量: 296.572
• InChiKey: BRDASRBDDJPKBT-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  15.6
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(N'-tert-butylformimidoyl)-2-(trimethylsilyl)-4-tert-butylpiperidine 、 碘甲烷 在 叔丁基锂 作用下， 生成 N-(N'-tert-butylformimidoyl)-2-(trimethylsilyl)-6-methyl-4-tert-butylpiperidine
  参考文献：
  名称：

  Stereochemistry of alkylation of .alpha.-lithio piperidines: differing effects of formamidine and urethane activating groups

  摘要：

  The stereochemistry of alkylation of alpha-lithio-N-(N'-tert-butylformimidoyl)-4-tert-butylpiperidines was studied. Monoalkylation proceeded to give equatorial 2-substituted piperidines, which in turn gave diequatorial 2,6-disubstituted piperidines when subjected to a second lithiation-alkylation procedure. The stereochemical result of the second alkylation is in contrast to alpha-lithio-2-substituted piperidines that are stabilized by the N-(tert-butoxycarbonyl) group; these gave the axial 6-substituted piperidine on treatment with electrophiles. A mechanistic rationalization of these results is given that invokes nonbonding interactions between the stabilizing groups and piperidine ring substituents.

  DOI：

  10.1021/jo00008a033
• 作为产物：
  描述：

  三甲基氯硅烷 、 N-(N'-tert-butylformimidoyl)-4-tert-butylpiperidine 在 叔丁基锂 作用下， 生成 N-(N'-tert-butylformimidoyl)-2-(trimethylsilyl)-4-tert-butylpiperidine
  参考文献：
  名称：

  Stereochemistry of alkylation of .alpha.-lithio piperidines: differing effects of formamidine and urethane activating groups

  摘要：

  The stereochemistry of alkylation of alpha-lithio-N-(N'-tert-butylformimidoyl)-4-tert-butylpiperidines was studied. Monoalkylation proceeded to give equatorial 2-substituted piperidines, which in turn gave diequatorial 2,6-disubstituted piperidines when subjected to a second lithiation-alkylation procedure. The stereochemical result of the second alkylation is in contrast to alpha-lithio-2-substituted piperidines that are stabilized by the N-(tert-butoxycarbonyl) group; these gave the axial 6-substituted piperidine on treatment with electrophiles. A mechanistic rationalization of these results is given that invokes nonbonding interactions between the stabilizing groups and piperidine ring substituents.

  DOI：

  10.1021/jo00008a033