N-[N'-phthaloyl-(2S)-alanyl]-(2S)-2-methyl-1,2,3,4-tetrahydroquinoline | 685881-94-1

• 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: N-[N'-phthaloyl-(2S)-alanyl]-(2S)-2-methyl-1,2,3,4-tetrahydroquinoline
• 英文别名: (2S)-2-methyl-N-[N-phthaloyl-(2S)-alanyl]-1,2,3,4-tetrahydroquinoline
• CAS: 685881-94-1
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: YVNQHUSNBMNEQK-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[N'-phthaloyl-(2S)-alanyl]-(2S)-2-methyl-1,2,3,4-tetrahydroquinoline 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 10.0h， 以95%的产率得到(S)-1,2,3,4-四氢-2-甲基喹啉
  参考文献：
  名称：

  N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines

  摘要：

  Acylation of heterocyclic amines with N-phthaloyl-(S)-alanyl chloride under kinetic resolution conditions resulted in the predominant formation of (S,S)-amides. The diastereoselectivity of resolution depended heavily on the structure of the resolved amine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.025
• 作为产物：
  描述：

  邻苯二甲酰基-L-丙氨酸 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 、 Petroleum ether 、 苯 为溶剂， 反应 40.0h， 生成 N-[N'-phthaloyl-(2S)-alanyl]-(2S)-2-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines

  摘要：

  Acylation of heterocyclic amines with N-phthaloyl-(S)-alanyl chloride under kinetic resolution conditions resulted in the predominant formation of (S,S)-amides. The diastereoselectivity of resolution depended heavily on the structure of the resolved amine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.025

文献信息

• Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines
  作者：D. A. Gruzdev、G. L. Levit、M. I. Kodess、V. P. Krasnov

  DOI：10.1007/s10593-012-1053-8

  日期：2012.8

  Enantiomers of 2-methyl-6-nitro-1,2,3,4-tetrahydroquinoline have been obtained by kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline in acylation with acyl chlorides of N-protected amino acids followed by regioselective nitration of the diastereoisomeric amides and acidic hydrolysis. The introduction of a trifluoroacetyl protecting group into the position 1 of the enantio pure nitro

  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。
• 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.
• Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides
  作者：Dmitry A. Gruzdev、Galina L. Levit、Victor P. Krasnov、Evgeny N. Chulakov、Liliya Sh. Sadretdinova、Aleksandr N. Grishakov、Marina A. Ezhikova、Mikhail I. Kodess、Valery N. Charushin

  DOI：10.1016/j.tetasy.2010.05.013

  日期：2010.4

  A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using N-phthaloyl-(S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-(S)-phenylalanyl and N-phthaloyl-(S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-(S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-(S)phenylalanyl chloride proved to be the most appropriate chiral acylating agent. (C) 2010 Elsevier Ltd. All rights reserved.