(S)-2-methyl-1-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline | 1403673-28-8

• 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: (S)-2-methyl-1-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline
• 英文别名: (2S,2'S)-2-methyl-1-(N'-phthaloyl-leucyl)-1,2,3,4-tetrahydroquinoline；2-((S)-4-methyl-1-((S)-2-methyl-3,4-dihydroquinolin-1(2H)-yl)-1-oxopentan-2-yl)isoindoline-1,3-dione；2-[(2S)-4-methyl-1-[(2S)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-1-oxopentan-2-yl]isoindole-1,3-dione
• CAS: 1403673-28-8
• 化学式: C₂₄H₂₆N₂O₃
• 分子量: 390.482
• InChiKey: OACZVPJEXPNWLL-KKSFZXQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (S)-2-methyl-1-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 24.0h， 以93%的产率得到(S)-1,2,3,4-四氢-2-甲基喹啉
  参考文献：
  名称：

  [EN] DUAL KINASE-BROMODOMAIN INHIBITORS
  [FR] INHIBITEURS DOUBLES DE KINASE-BROMODOMAINE

  摘要：

  提供的是公式(I)的化合物，它们是激酶和溴结构域蛋白的双重抑制剂。本公开还涉及包含这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法，特别是治疗多发性骨髓瘤癌症的方法，以及相关的用途。

  公开号：

  WO2021243421A1
• 作为产物：
  描述：

  苯酐 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 (S)-2-methyl-1-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  [EN] DUAL KINASE-BROMODOMAIN INHIBITORS
  [FR] INHIBITEURS DOUBLES DE KINASE-BROMODOMAINE

  摘要：

  提供的是公式(I)的化合物，它们是激酶和溴结构域蛋白的双重抑制剂。本公开还涉及包含这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法，特别是治疗多发性骨髓瘤癌症的方法，以及相关的用途。

  公开号：

  WO2021243421A1

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.
• 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.
• New chiral proline-based catalysts for silicon and zirconium oxides-promoted asymmetric Biginelli reaction
  作者：Yulia A. Titova、Dmitry A. Gruzdev、Olga V. Fedorova、Olga A. Alisienok、Anna N. Murashkevich、Victor P. Krasnov、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.1007/s10593-018-2285-z

  日期：2018.4

  4-Hydroxy-(2S)-prolines bearing 3,4-dihydro-2H-1,4-benzoxazine or 1,2,3,4-tetrahydroquinoline fragments were synthesized and studied as chiral catalysts in the Biginelli reaction. The target product ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate was obtained with 54% enantiomeric excess (ee). An increase in ee values of the reaction product up to 76% was observed in the presence of nanosized oxides SiO2-ZrO2 as heterogeneous promoters.