N-phthaloyl-(S)-2-phenylglycyl chloride | 1239896-95-7

• 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-phthaloyl-(S)-2-phenylglycyl chloride
• 英文别名: (2S)-2-(1,3-dioxoisoindol-2-yl)-2-phenylacetyl chloride
• CAS: 1239896-95-7
• 化学式: C₁₆H₁₀ClNO₃
• 分子量: 299.713
• InChiKey: XVNYYFQWEYONQY-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phthaloyl-(S)-2-phenylglycyl chloride 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates

  摘要：

  The regiospecific and stereoselective 1,2-migration reaction of dialkyl alpha-diazophosphonates for the synthesis of beta-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)(4)PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to beta-amino (E)-enylphosphonates in moderate to good yields.

  DOI：

  10.1055/s-0035-1560373
• 作为产物：
  描述：

  2(S)-2-(1,3-dioxoisoindolin-2-yl)-2-phenylacetic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 正己烷 、 苯 为溶剂， 以85%的产率得到N-phthaloyl-(S)-2-phenylglycyl chloride
  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.
• 1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates
  作者：Zhiwei Miao、Haihong Ge、Shuang Liu、Yan Cai、Yuchao Sun

  DOI：10.1055/s-0035-1560373

  日期：——

  The regiospecific and stereoselective 1,2-migration reaction of dialkyl alpha-diazophosphonates for the synthesis of beta-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)(4)PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to beta-amino (E)-enylphosphonates in moderate to good yields.