(3S)-2,3-dihydro-3-methyl-N-[N-phthaloyl-(2S)-2-phenylglycyl]-4H-1,4-benzoxazine | 1239896-99-1

• 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: (3S)-2,3-dihydro-3-methyl-N-[N-phthaloyl-(2S)-2-phenylglycyl]-4H-1,4-benzoxazine
• 英文别名: 2-[(1S)-2-[(3S)-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl]-2-oxo-1-phenylethyl]isoindole-1,3-dione
• CAS: 1239896-99-1
• 化学式: C₂₅H₂₀N₂O₄
• 分子量: 412.445
• InChiKey: LDYVIBNXQIKGJC-AOMKIAJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-phthaloyl-(S)-2-phenylglycyl chloride 、 3-甲基-3,4-二氢-2H-1,4-苯并噁嗪 以 甲苯 为溶剂， 反应 6.0h， 生成 (3R)-2,3-dihydro-3-methyl-N-[N-phthaloyl-(2S)-2-phenylglycyl]-4H-1,4-benzoxazine 、 (3S)-2,3-dihydro-3-methyl-N-[N-phthaloyl-(2S)-2-phenylglycyl]-4H-1,4-benzoxazine 、 (R)-3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine 、 (S)-3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
  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

文献信息

• 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.