benzyl 1-(methoxycarbonyl)-2-(4-methoxyphenylamino)-1,2-diphenylethylcarbamate | 1309440-15-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: benzyl 1-(methoxycarbonyl)-2-(4-methoxyphenylamino)-1,2-diphenylethylcarbamate
• 英文别名: methyl (2R,3R)-3-(4-methoxyanilino)-2,3-diphenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1309440-15-0
• 化学式: C₃₁H₃₀N₂O₅
• 分子量: 510.59
• InChiKey: QTRWXTVVDUWALY-GRKNLSHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 1-(methoxycarbonyl)-2-(4-methoxyphenylamino)-1,2-diphenylethylcarbamate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 碳酸氢钠 作用下， 以 乙醇 、 乙酸乙酯 、 水 为溶剂， 反应 2.0h， 生成 (2R,3R)-methyl 3-(4-methoxyphenylamino)-2-amino-2,3-diphenylpropanoate
  参考文献：
  名称：

  Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

  摘要：

  The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh-2(OAc)(4) and chiral Bronsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-alpha-substituted alpha,beta-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/ja201589k
• 作为产物：
  描述：

  氨基甲酸苄酯 、 a-叠氮基-苯乙酸甲酯 、 N-亚苄基-4-甲氧基苯胺 在 rhodium(II) acetate dimer 、 L-酒石酸 、 (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以85%的产率得到benzyl 1-(methoxycarbonyl)-2-(4-methoxyphenylamino)-1,2-diphenylethylcarbamate
  参考文献：
  名称：

  Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

  摘要：

  The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh-2(OAc)(4) and chiral Bronsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-alpha-substituted alpha,beta-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/ja201589k

文献信息

• Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines
  作者：Jun Jiang、Hua-Dong Xu、Jian-Bei Xi、Bai-Yan Ren、Feng-Ping Lv、Xin Guo、Li-Qin Jiang、Zhi-Yong Zhang、Wen-Hao Hu

  DOI：10.1021/ja201589k

  日期：2011.6.8

  The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh-2(OAc)(4) and chiral Bronsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-alpha-substituted alpha,beta-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.