trans-N-(Diphenylphosphinyl)-3-methylcyclohexylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-N-(Diphenylphosphinyl)-3-methylcyclohexylamine
• 英文别名: (1R,3R)-N-diphenylphosphoryl-3-methylcyclohexan-1-amine
• 化学式: C₁₉H₂₄NOP
• 分子量: 313.379
• InChiKey: DAYDBOCBGDHHHD-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-N-diphenylphosphoryl-3-methylcyclohexan-1-imine 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以63%的产率得到trans-N-(Diphenylphosphinyl)-3-methylcyclohexylamine
  参考文献：
  名称：

  Stereoselective Hydride Reductions of Cyclic N-Diphenylphosphinyl Imines. Highly Diastereoselective Syntheses of Protected Primary Amines

  摘要：

  Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.

  DOI：

  10.1021/jo00128a009

文献信息

• Stereoselective Hydride Reductions of Cyclic N-Diphenylphosphinyl Imines. Highly Diastereoselective Syntheses of Protected Primary Amines
  作者：Robert O. Hutchins、Jeffrey Adams、Melvin C. Rutledge

  DOI：10.1021/jo00128a009

  日期：1995.11

  Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.