(2S)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline | 1416453-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2S)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-[(2S)-3-cyclohexyl-1-[(2S)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-1-oxopropan-2-yl]isoindole-1,3-dione
• CAS: 1416453-25-2
• 化学式: C₂₇H₃₀N₂O₃
• 分子量: 430.547
• InChiKey: NRNHMNHRVNTLTM-UUOWRZLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-phthaloyl-3-cyclohexyl-(S)-alanyl chloride 、 1,2,3,4-四氢喹哪啶 以 二氯甲烷 为溶剂， 反应 6.0h， 以38%的产率得到(2S)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains

  摘要：

  A comparative study of the acylative kinetic resolution of racemic 2-methyl-1,2,3,4 tetrahydroquinoline and 3,4-dihydro-3-methyl-2H-1[,4]benzoxazine using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains has been carried out. The influence of steric factors on the stereoselectivity of the acylation was demonstrated. The (S)-enantiomers of the heterocyclic amines (ee >99%) were obtained in good yields via a kinetic resolution protocol using N-phthaloyl-(S)-leucyl chloride. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.001