(R)-2-[(2S,5S)-2,5-diphenylpyrrolidin-1-ylamino]-4-methylpentanenitrile | 1030379-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-2-[(2S,5S)-2,5-diphenylpyrrolidin-1-ylamino]-4-methylpentanenitrile
• 英文别名: (2R)-2-[[(2S,5S)-2,5-diphenylpyrrolidin-1-yl]amino]-4-methylpentanenitrile
• CAS: 1030379-53-3
• 化学式: C₂₂H₂₇N₃
• 分子量: 333.476
• InChiKey: QVHKQBRQKZEEJL-FSSWDIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,5S)-1-[(3-methylbutylidene)amino]-2,5-diphenylpyrrolidine 、 三甲基氰硅烷 在 氯化二乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 72.33h， 以83%的产率得到(R)-2-[(2S,5S)-2,5-diphenylpyrrolidin-1-ylamino]-4-methylpentanenitrile
  参考文献：
  名称：

  Experimental and theoretical studies on the asymmetric cyanosilylation of C2-symmetric hydrazones

  摘要：

  The Et2AlCl-promoted asymmetric cyanosilylation of (2S,5S)-1-amino-2,5-diphenylpyrrolidine-derived aliphatic hydrazones affords the corresponding hydrazino nitriles with high diastereoselectivity (dr 91:9 to >99:1). The resolving properties of the auxiliary allowed the isolation of the adducts as single diastereoisomers (dr >99:1) in good yields (80-84%) after chromatography. Ab initio MO calculations indicated that the formation of the hydrazone-promoter complex inhibits n ->pi conjugation and increases the nucleophilicity of the dialkylamino nitrogen, enabling the basic activation of TMSCN. The calculated geometries for these complexes show the shielding of the Si face of the C=N bond by one of the phenyl groups in the auxiliary, providing an explanation for the observed absolute configuration. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.020