N-((S)-1-Phenyl-ethyl)-N-((R)-1-phenyl-ethyl)-benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((S)-1-Phenyl-ethyl)-N-((R)-1-phenyl-ethyl)-benzamide
• 英文别名: N-[(1R)-1-phenylethyl]-N-[(1S)-1-phenylethyl]benzamide
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: IXEDUCBVEKEPOB-KDURUIRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲基锂 、 N-benzyl-N-[(1S)-1-phenylethyl]benzamide 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到N-((S)-1-Phenyl-ethyl)-N-((R)-1-phenyl-ethyl)-benzamide
  参考文献：
  名称：

  ‘meso-Selective’ functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation

  摘要：

  Lithiation and methylation of amide and carbamate derivatives of alpha-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-alpha-methylbenzylamine derivatives, Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-alpha-methylbenzylamine as starting material, oxidative cleavage provides a new asymmetric route to phenylglycine. Other electrophiles give a range of stereochemical outcomes, apparently depending on the stereospecificity of their reactions with a pair of diastereoisomeric organolithiums of low to moderate configurational stability. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00154-5