(R)-2-methyl-1-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline | 1403673-29-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-methyl-1-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline
• CAS: 1403673-29-9
• 化学式: C₂₄H₂₆N₂O₃
• 分子量: 390.482
• InChiKey: OACZVPJEXPNWLL-IERDGZPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (alphaS)-1,3-二氢-alpha-(2-甲基丙基)-1,3-二氧代-2H-异吲哚-2-乙酸 在 草酰氯 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 11.0h， 生成 (R)-2-methyl-1-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  6-硝基和6-氨基-2-甲基-1,2,3,4-四氢喹啉对映体的合成

  摘要：

  通过用N-保护的氨基的酰氯酰化酰化外消旋的2-甲基-1,2,3,4-四氢喹啉，可以动态拆分2-甲基-6-硝基-1,2,3,4-四氢喹啉的对映异构体。酸，然后将非对映异构酰胺进行区域选择性硝化并进行酸性水解。将三氟乙酰基保护基引入对映体纯硝基化合物的1位，然后还原，得到（S）-6-氨基-2-甲基-1-三氟乙酰基-1,2,3,4-四氢喹啉高产。

  DOI：

  10.1007/s10593-012-1053-8

文献信息

• Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains
  作者：Dmitry A. Gruzdev、Galina L. Levit、Victor P. Krasnov

  DOI：10.1016/j.tetasy.2012.11.001

  日期：2012.12

  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.
• A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines
  作者：Dmitry A. Gruzdev、Evgeny N. Chulakov、Galina L. Levit、Marina A. Ezhikova、Mikhail I. Kodess、Victor P. Krasnov

  DOI：10.1016/j.tetasy.2013.07.024

  日期：2013.10

  The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine, and their non-fluorinated analogues with (S)-naproxen and N-phthaloyl-(S)-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with (S)-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N-phthaloyl-(S)-amino acyl chlorides. A method for the preparation of enantiopure (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (ee >99%) was developed. (C) 2013 Elsevier Ltd. All rights reserved.