N-(N'-tert-butylformimidoyl)-2-methyl-4-tert-butylpiperidine | 133165-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(N'-tert-butylformimidoyl)-2-methyl-4-tert-butylpiperidine
• 英文别名: N-tert-butyl-1-[(2R,4R)-4-tert-butyl-2-methylpiperidin-1-yl]methanimine
• CAS: 133165-13-6；141069-16-1
• 化学式: C₁₅H₃₀N₂
• 分子量: 238.417
• InChiKey: GFKPTVDWOIMCNU-CHWSQXEVSA-N

物化性质

• 沸点：
  302.8±25.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(N'-tert-butylformimidoyl)-2-methyl-4-tert-butylpiperidine 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 生成 cis-4-tert-butyl-2-methylpiperidine
  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：

  N-(N'-tert-butylformimidoyl)-4-tert-butylpiperidine 、 碘甲烷 在 叔丁基锂 作用下， 生成 N-(N'-tert-butylformimidoyl)-2-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

文献信息

• Stereoselective nucleophilic addition to conformationally constrained piperidines. An efficient route to 2-axial-6-equatorial disubstituted piperidines.
  作者：A.I. Meyers、Thomas T. Shawe、Levi Gottlieb

  DOI：10.1016/s0040-4039(00)91562-4

  日期：1992.2

  Addition of RMgX to 2-methoxy-4-tert-butylpiperidine formamidine in dichloromethane or ether gives good to excellent yields of axial product.
• Stereochemistry of alkylation of .alpha.-lithio piperidines: differing effects of formamidine and urethane activating groups
  作者：Thomas T. Shawe、A. I. Meyers

  DOI：10.1021/jo00008a033

  日期：1991.4

  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.