(3S)-3,4-dihydro-3-methyl-4-[N-phthaloyl-(S)-leucyl]-2H-[1,4]benzoxazine | 1416453-32-1

• 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: (3S)-3,4-dihydro-3-methyl-4-[N-phthaloyl-(S)-leucyl]-2H-[1,4]benzoxazine
• 英文别名: (3S,2'S)-3,4-dihydro-3-methyl-4-(N'-phthaloylleucyl)-2H-1,4-benzoxazine；2-[(2S)-4-methyl-1-[(3S)-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl]-1-oxopentan-2-yl]isoindole-1,3-dione
• CAS: 1416453-32-1
• 化学式: C₂₃H₂₄N₂O₄
• 分子量: 392.455
• InChiKey: MKURCDCOBKJXGZ-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3,4-dihydro-3-methyl-4-[N-phthaloyl-(S)-leucyl]-2H-[1,4]benzoxazine 在 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以95%的产率得到(2S)-2-amino-4-methyl-1-[(3S)-3-methyl-2,3-dihydro-4H-1,4-benzoxazin-4-yl]pentan-1-one
  参考文献：
  名称：

  New chiral proline-based catalysts for silicon and zirconium oxides-promoted asymmetric Biginelli reaction

  摘要：

  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.

  DOI：

  10.1007/s10593-018-2285-z
• 作为产物：
  描述：

  N-phthalimide-L-leucinyl chloride 、 3-甲基-3,4-二氢-2H-1,4-苯并噁嗪 以 二氯甲烷 为溶剂， 反应 6.0h， 以77.6%的产率得到
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.07.024

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.