N-(N'-tert-butylformimidoyl)-4-tert-butylpiperidine | 89656-21-3

• 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)-4-tert-butylpiperidine
• 英文别名: (E)-N-tert-Butyl-1-(4-tert-butylpiperidin-1-yl)methanimine；N-tert-butyl-1-(4-tert-butylpiperidin-1-yl)methanimine
• CAS: 89656-21-3
• 化学式: C₁₄H₂₈N₂
• 分子量: 224.39
• InChiKey: JDUDLZJVHRHSFB-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 0.6 Torr)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 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)-4-tert-butylpiperidine 在 叔丁基锂 作用下， 反应 4.0h， 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：

  丙基氯化镁 、 Piperidine,4-(1,1-dimethylethyl)-1-[[(1,1-dimethylethyl)imino]methyl]-2-methoxy-,trans- 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 N-(N'-tert-butylformimidoyl)-4-tert-butylpiperidine 、 Piperidine,4-(1,1-dimethylethyl)-1-[[(1,1-dimethylethyl)imino]methyl]-2-propyl-,trans- 、 Piperidine,4-(1,1-dimethylethyl)-1-[[(1,1-dimethylethyl)imino]methyl]-2-propyl-,trans-
  参考文献：
  名称：

  Stereoselective nucleophilic addition to conformationally constrained piperidines. An efficient route to 2-axial-6-equatorial disubstituted piperidines.

  摘要：

  Addition of RMgX to 2-methoxy-4-tert-butylpiperidine formamidine in dichloromethane or ether gives good to excellent yields of axial product.

  DOI：

  10.1016/s0040-4039(00)91562-4

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.