tert-Butyl 2-<amino>-5-oxo-3-phenylhexanoate

• 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: tert-Butyl 2-<amino>-5-oxo-3-phenylhexanoate
• 英文别名: tert-Butyl 2-[(bis(methylthio)methylene)amino]-5-oxo-3-phenylhexanoate；tert-butyl (2S,3R)-2-[bis(methylsulfanyl)methylideneamino]-5-oxo-3-phenylhexanoate
• 化学式: C₁₉H₂₇NO₃S₂
• 分子量: 381.56
• InChiKey: BCSMXAPBHOEXDH-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-Butyl 2-<amino>-5-oxo-3-phenylhexanoate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95%的产率得到trans-5-(tert-Butoxycarbonyl)-2-methyl-4-phenyl-Δ¹-pyrroline
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted Glutamic Acid Derivatives via Michael Additions of N-[Bis(methylthio)methylene]glycinates under Solid-Liquid Phase Transfer Catalysis

  摘要：

  Michael additions of the enolates of ethyl and tert-butyl N-[bis(methylthio)methylene]glycinates with alpha,beta-unsaturated esters and ketones under solid-liquid phase transfer catalysis allowed for the highly diastereoselective synthesis of substituted glutamic acid derivatives through a transition state chelation-controlled by the catalyst with a like approach of reactants. Selective removal of the iminodithiocarbonate protecting group with concomitant cyclization gave rise to 3-substituted pyroglutamates and 1,3,4-trisubstitued Delta(1)-pyrrolines with retention of configuration.

  DOI：

  10.1021/jo00126a020
• 作为产物：
  描述：

  tert-Butyl N-glycinate 、 苄叉丙酮 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以80%的产率得到tert-Butyl 2-<amino>-5-oxo-3-phenylhexanoate
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted Glutamic Acid Derivatives via Michael Additions of N-[Bis(methylthio)methylene]glycinates under Solid-Liquid Phase Transfer Catalysis

  摘要：

  Michael additions of the enolates of ethyl and tert-butyl N-[bis(methylthio)methylene]glycinates with alpha,beta-unsaturated esters and ketones under solid-liquid phase transfer catalysis allowed for the highly diastereoselective synthesis of substituted glutamic acid derivatives through a transition state chelation-controlled by the catalyst with a like approach of reactants. Selective removal of the iminodithiocarbonate protecting group with concomitant cyclization gave rise to 3-substituted pyroglutamates and 1,3,4-trisubstitued Delta(1)-pyrrolines with retention of configuration.

  DOI：

  10.1021/jo00126a020

文献信息

• Diastereoselective Synthesis of Substituted Glutamic Acid Derivatives via Michael Additions of N-[Bis(methylthio)methylene]glycinates under Solid-Liquid Phase Transfer Catalysis
  作者：Carlos Alvarez-Ibarra、Aurelio G. Csakye、Mercedes Maroto、M. Luz Quiroga

  DOI：10.1021/jo00126a020

  日期：1995.10

  Michael additions of the enolates of ethyl and tert-butyl N-[bis(methylthio)methylene]glycinates with alpha,beta-unsaturated esters and ketones under solid-liquid phase transfer catalysis allowed for the highly diastereoselective synthesis of substituted glutamic acid derivatives through a transition state chelation-controlled by the catalyst with a like approach of reactants. Selective removal of the iminodithiocarbonate protecting group with concomitant cyclization gave rise to 3-substituted pyroglutamates and 1,3,4-trisubstitued Delta(1)-pyrrolines with retention of configuration.