(S_S,2S,3S)-(+)-ethyl 2-N-(diphenylmethylideneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate | 749253-91-6

• 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_S,2S,3S)-(+)-ethyl 2-N-(diphenylmethylideneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate
• 英文别名: ethyl (S_S,2S,3S)-(-)-2-N-(diphenylmethyleneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate；ethyl (2S,3S)-2-(benzhydrylideneamino)-3-[[(S)-(4-methylphenyl)sulfinyl]amino]-3-phenylpropanoate
• CAS: 749253-91-6
• 化学式: C₃₁H₃₀N₂O₃S
• 分子量: 510.657
• InChiKey: HXESXUNBKOLZFE-PEWNMUGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S_S,2S,3S)-(+)-ethyl 2-N-(diphenylmethylideneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate 在 水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 (S,E)-N-benzylidene-4-methylbenzenesulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of anti- and syn-2,3-Diamino Esters Using Sulfinimines. Water and Concentration Effects

  摘要：

  In the absence of water, an excess of the lithium enolate of N-(diphenylmethylene)glycine ethyl ester (4) adds to sulfinimines to give syn-2,3-diamino esters 6, and in the presence of water, this enolate gives the anti-2,3-diamino esters 5. These unusual results are interpreted in terms of those factors that inhibit the retro-Mannich fragmentation in the diamino esters.

  DOI：

  10.1021/ol063058c
• 作为产物：
  描述：

  二苯亚甲基甘氨酸乙酯 、 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.33h， 以89%的产率得到(S_S,2S,3S)-(+)-ethyl 2-N-(diphenylmethylideneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate
  参考文献：
  名称：

  Asymmetric Synthesis of syn-(2R,3S)- and anti-(2S,3S)-Ethyl Diamino-3-phenylpropanoates from N-(Benzylidene)-p-toluenesulfinamide and Glycine Enolates

  摘要：

  Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.

  DOI：

  10.1021/ol048981y

文献信息

• Asymmetric Synthesis of <i>s</i><i>yn</i>-(2<i>R</i>,3<i>S</i>)<i>- </i>and <i>a</i><i>nti</i>-(<i>2S</i>,3<i>S</i>)-Ethyl Diamino-3-phenylpropanoates from <i>N</i>-(Benzylidene)-<i>p</i>-toluenesulfinamide and Glycine Enolates
  作者：Franklin A. Davis、Jianghe Deng

  DOI：10.1021/ol048981y

  日期：2004.8.1

  Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.
• Asymmetric Synthesis of <i>anti</i>- and <i>syn</i>-2,3-Diamino Esters Using Sulfinimines. Water and Concentration Effects
  作者：Franklin A. Davis、Yanfeng Zhang、Hui Qiu

  DOI：10.1021/ol063058c

  日期：2007.3.1

  In the absence of water, an excess of the lithium enolate of N-(diphenylmethylene)glycine ethyl ester (4) adds to sulfinimines to give syn-2,3-diamino esters 6, and in the presence of water, this enolate gives the anti-2,3-diamino esters 5. These unusual results are interpreted in terms of those factors that inhibit the retro-Mannich fragmentation in the diamino esters.