8-Phenylmenthyl N--L-alaninate

• 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: 8-Phenylmenthyl N--L-alaninate
• 英文别名: 8-Phenylmenthyl N-(bis(methylthio)methylene)-L-alaninate；[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2S)-2-[bis(methylsulfanyl)methylideneamino]propanoate
• 化学式: C₂₂H₃₃NO₂S₂
• 分子量: 407.642
• InChiKey: RANBISXEFXYCDO-UKBAYJJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  89.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氟磺酸甲酯 、 8-Phenylmenthyl N-glycinate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 8-Phenylmenthyl N--L-alaninate 、 8-Phenylmenthyl N--D-alaninate
  参考文献：
  名称：

  Asymmetric Alkylation of 8-Phenylmenthyl N-[Bis(methylthio)methylene]glycinate Enolates. Synthesis of D- and L-.alpha.-Amino Acids from a Single Chiral Precursor

  摘要：

  The herein described studies on the enolization and subsequent alkylation of the acyclic glycine title ester evidence the involvement of the kinetics of the alkylation step on the stereochemical outcome of the overall process, apart from that of the deprotonation sequence itself. Careful choice of reaction conditions allow for the selective obtention of alpha-amino acids either of the L- or the D-series without the need of changing the chiral inducer: deprotonation with LDA or (t)BuLi followed by reaction with alkyl triflates gives rise to the 2R alpha-amino acids, whereas the 2S isomers can be obtained by deprotonation with KO(t)Bu followed by reaction with alkyl halides.

  DOI：

  10.1021/jo00129a038

文献信息

• Asymmetric Alkylation of 8-Phenylmenthyl N-[Bis(methylthio)methylene]glycinate Enolates. Synthesis of D- and L-.alpha.-Amino Acids from a Single Chiral Precursor
  作者：Carlos Alvarez-Ibarra、Aurelio G. Csakye、Raquel Maroto、M. Luz Quiroga

  DOI：10.1021/jo00129a038

  日期：1995.12

  The herein described studies on the enolization and subsequent alkylation of the acyclic glycine title ester evidence the involvement of the kinetics of the alkylation step on the stereochemical outcome of the overall process, apart from that of the deprotonation sequence itself. Careful choice of reaction conditions allow for the selective obtention of alpha-amino acids either of the L- or the D-series without the need of changing the chiral inducer: deprotonation with LDA or (t)BuLi followed by reaction with alkyl triflates gives rise to the 2R alpha-amino acids, whereas the 2S isomers can be obtained by deprotonation with KO(t)Bu followed by reaction with alkyl halides.