methyl 2-phenyl-2-(1-phenylethylamino)acetate

• 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: methyl 2-phenyl-2-(1-phenylethylamino)acetate
• 英文别名: methyl (2R)-2-phenyl-2-[[(1S)-1-phenylethyl]amino]acetate
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: RAXNXVSZSKUIIH-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (S)-2-phenyl-2-((1-phenylethyl)imino)acetate 在 C₁₆H₁₇ClN₂O₂ 、 三氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl 2-phenyl-2-(1-phenylethylamino)acetate 、 (S)-methyl 2-((S)-1-phenylethylamino)-2-phenylacetate
  参考文献：
  名称：

  Highly Stereoselective Metal-Free Catalytic Reduction of Imines: An Easy Entry to Enantiomerically Pure Amines and Natural and Unnatural α-Amino Esters

  摘要：

  A highly efficient catalytic stereoselective ketimine reduction is described. The combination of an inexpensive chiral organocatalyst, easily prepared in a single step, and of a very cheap removable chiral auxiliary allowed us to obtain enantiomerically pure amino compounds. The methodology allowed synthesis of chiral secondary and primary amines and natural and unnatural amino esters in high yields often with total control of the absolute stereochemistry.

  DOI：

  10.1021/ol900945h

文献信息

• Diastereoselective addition of higher order cuprates and zinc-copper reagents to imines derived from (S)-1-phenylethylamine
  作者：Marco Bandini、Pier Giorgio Cozzi、Achille Umani-Ronchi、Marzia Villa

  DOI：10.1016/s0040-4020(99)00418-4

  日期：1999.6

  The diastereoselective addition of higher order (H.O.) cuprates and zinc-copper reagents to aliphatic and aromatic chiral imines derived from (S)-1-phenylethylamine was examined. Aliphatic chiral imines react with (Allyl)2CuCNLi2 and (n-Bu)2Cu(CN)Li2 in the presence of BF3·Et2O and Me3SiCl in high diastereoselection, while c-C6H11Cu(CN)ZnI and AllylCu(CN)ZnBr afford chiral amines in comparable yields

  考察了向（S）-1-苯基乙胺衍生的脂族和芳族手性亚胺的非对映选择性地添加了高阶（HO）铜酸盐和锌铜试剂。脂族的手性亚胺与（烯丙基）反应2 CuCNLi 2和（正丁基）2的Cu（CN）栗2在BF的存在3 ·的Et 2 O和我3的SiCl在高diastereoselection，而CC 6 ħ 11的Cu（CN ZnI和烯丙基Cu（CN）ZnBr可以在不添加添加剂的情况下以相当的收率得到手性胺。此外，据报道合成了针对δ-氨基酸的关键中间体。