E-(2S,7S)-2,7-diamino-oct-4-enedioic acid di-tert-butyl ester | 221303-44-2

• 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: E-(2S,7S)-2,7-diamino-oct-4-enedioic acid di-tert-butyl ester
• 英文别名: ditert-butyl (E,2S,7S)-2,7-diaminooct-4-enedioate
• CAS: 221303-44-2
• 化学式: C₁₆H₃₀N₂O₄
• 分子量: 314.425
• InChiKey: FWWCGXILXQNMGB-BRQSLIGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  E-(2S,7S)-2,7-diamino-oct-4-enedioic acid di-tert-butyl ester 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 以56%的产率得到(2S,7S)-2,7-diaminooctanedioic acid di-tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of bis-α-amino acid esters via asymmetric phase-transfer catalysis

  摘要：

  Application of N-anthracenylmethyl dihydrocinchonidinium bromide quaternary ammonium phase-transfer catalysts to the enantio- and diastereoselective synthesis of a series of bis-alpha-amino acid esters is reported. Under liquid-liquid phase-transfer conditions the target amino acid esters are obtained with high enantiomeric excess (greater than or equal to 95%e.e.) via alkylation of two molecules of a benzophenone-derived glycine-imine with an appropriate dibromide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02615-x
• 作为产物：
  描述：

  ditert-butyl (E,2S,7S)-2,7-bis(benzhydrylideneamino)oct-4-enedioate 在 柠檬酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 E-(2S,7S)-2,7-diamino-oct-4-enedioic acid di-tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of bis-α-amino acid esters via asymmetric phase-transfer catalysis

  摘要：

  Application of N-anthracenylmethyl dihydrocinchonidinium bromide quaternary ammonium phase-transfer catalysts to the enantio- and diastereoselective synthesis of a series of bis-alpha-amino acid esters is reported. Under liquid-liquid phase-transfer conditions the target amino acid esters are obtained with high enantiomeric excess (greater than or equal to 95%e.e.) via alkylation of two molecules of a benzophenone-derived glycine-imine with an appropriate dibromide. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02615-x

文献信息

• An enantioselective approach to bis-α-amino acids
  作者：B Lygo、J Crosby、J.A Peterson

  DOI：10.1016/s0040-4020(01)00536-1

  日期：2001.7

  In this paper, we describe details of a study into the asymmetric synthesis of bis-alpha -amino acids via alkylation of a benzophenone-derived glycine imine under phase-transfer conditions. By employing chiral quaternary ammonium salts derived from cinchona alkaloids it was found that the target bis-amino acids can be produced in good overall yield, and with high levels of stereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enantioselective synthesis of bis-α-amino acid esters via asymmetric phase-transfer catalysis
  作者：Barry Lygo、John Crosby、Justine A. Peterson

  DOI：10.1016/s0040-4039(98)02615-x

  日期：1999.2

  Application of N-anthracenylmethyl dihydrocinchonidinium bromide quaternary ammonium phase-transfer catalysts to the enantio- and diastereoselective synthesis of a series of bis-alpha-amino acid esters is reported. Under liquid-liquid phase-transfer conditions the target amino acid esters are obtained with high enantiomeric excess (greater than or equal to 95%e.e.) via alkylation of two molecules of a benzophenone-derived glycine-imine with an appropriate dibromide. (C) 1999 Elsevier Science Ltd. All rights reserved.