(2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline | 1239896-96-8

• 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-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-[(2S)-1-[(2S)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-1-oxo-3-phenylpropan-2-yl]isoindole-1,3-dione
• CAS: 1239896-96-8
• 化学式: C₂₇H₂₄N₂O₃
• 分子量: 424.499
• InChiKey: LUYOWRXTECNGEP-UUOWRZLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline 在 盐酸 、 水 、 溶剂黄146 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 12.0h， 以90%的产率得到(S)-1,2,3,4-四氢-2-甲基喹啉
  参考文献：
  名称：

  Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.05.013
• 作为产物：
  描述：

  N-邻苯二甲酰基-L-苯丙氨酸 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 6.0h， 生成 (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline 、 (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-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

文献信息

• Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides
  作者：Galina L. Levit、Dmitry A. Gruzdev、Victor P. Krasnov、Evgeny N. Chulakov、Liliya Sh. Sadretdinova、Marina A. Ezhikova、Mikhail I. Kodess、Valery N. Charushin

  DOI：10.1016/j.tetasy.2010.12.017

  日期：2011.1

  The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic

  使用N-邻苯二甲酰基- （S）-的酰氯进行外消旋的2-甲基-1,2,3,4-四氢喹啉和2,3-二氢-3-甲基-4 H -1,4-苯并恶嗪的酰基动力学拆分已经进行了作为手性拆分剂的苯丙氨酸，N-邻苯二甲酰基-3-（4-硝基苯基）-（S）-丙氨酸和N-邻苯二甲酰基-O-甲基-（S）-酪氨酸的制备。结果表明，酰基化动力学拆分的有效性取决于酰化剂苯基片段中取代基的电子效应，并随着苯基片段中对位取代基（OMe> H> NO 2）的给电子性质而增加。的N-邻苯二甲酰基-3-芳基-（S）-丙氨酰氯增加; 在降低的温度下进行该过程也有助于提高动力学分辨率。
• 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。
• 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.