N-[N'-phthaloyl-(2S)-alanyl]-(3S)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine | 685881-93-0

• 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]-(3S)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine
• 英文别名: (3S)-2,3-dihydro-3-methyl-N-[N-phthaloyl-(2S)-alanyl]-4H-1,4-benzoxazine；2-[(2S)-1-[(3S)-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl]-1-oxopropan-2-yl]isoindole-1,3-dione
• CAS: 685881-93-0
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: WVPPWGQMLZBLMQ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N-[N'-phthaloyl-(2S)-alanyl]-(3S)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 10.0h， 以93%的产率得到(S)-3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
  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：

  (S)-2-(1,3-dioxoisoindolin-2-yl)butanoic acid 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 N-[N'-phthaloyl-(2S)-alanyl]-(3S)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine
  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

• 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.
• 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.
• N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines
  作者：Victor P. Krasnov、Galina L. Levit、Mikhail I. Kodess、Valery N. Charushin、Oleg N. Chupakhin

  DOI：10.1016/j.tetasy.2004.01.025

  日期：2004.3

  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.