N-(S)-1-carboxyethyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide | 952657-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: N-(S)-1-carboxyethyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide
• 英文别名: (2S)-2-(6,8,17,19-tetraoxo-7-oxa-18-azaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-18-yl)propanoic acid
• CAS: 952657-18-0
• 化学式: C₂₇H₁₃NO₇
• 分子量: 463.403
• InChiKey: RBKFZPFVCDEJCI-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(S)-1-carboxyethyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide 、 (S)-1-(2-methylpropyl)-2-oxo-2-(1H,1H,2H,2H-perfluorodecyloxy)-ethylammonium 4-toluenesulfonate 在 咪唑 、 盐酸 作用下， 反应 1.5h， 以72%的产率得到N-(S)-1-carboxyethyl-N'-(S)-3-methyl-1-(oxo(1H,1H,2H,2H-perfluorodecyloxy)methyl)butyl-3,4,9,10-perylenetetracarboxyldiimide
  参考文献：
  名称：

  Facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides involving α-amino acids

  摘要：

  A facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides (PDIs) has been developed and the first two nonracemic chiral amphiphilic PDIs have been synthesized. The key building blocks, AB bifunctional 3,4,9, 10-perylenetetracarboxylic-3,4-anhydride-9, 10-imides, were prepared conveniently from enantiomerically pure alpha-amino acids, which were introduced as the steric and stereochemical controlling units. Such building blocks allow the incorporation of sterically and stereochemically controlled PDI moieties into both terminal and inner positions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.099
• 作为产物：
  描述：

  L-丙氨酸 、 perylene-3,4,9,10-tetracarboxylic acid monoanhydride monopotassium carboxylate 在 咪唑 、 氢氧化钾 、 盐酸 作用下， 反应 2.0h， 以99%的产率得到N-(S)-1-carboxyethyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide
  参考文献：
  名称：

  Facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides involving α-amino acids

  摘要：

  A facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides (PDIs) has been developed and the first two nonracemic chiral amphiphilic PDIs have been synthesized. The key building blocks, AB bifunctional 3,4,9, 10-perylenetetracarboxylic-3,4-anhydride-9, 10-imides, were prepared conveniently from enantiomerically pure alpha-amino acids, which were introduced as the steric and stereochemical controlling units. Such building blocks allow the incorporation of sterically and stereochemically controlled PDI moieties into both terminal and inner positions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.099

文献信息

• Facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides involving α-amino acids
  作者：Runkun Sun、Chenming Xue、Mariam Owak、Ralf M. Peetz、Shi Jin

  DOI：10.1016/j.tetlet.2007.07.099

  日期：2007.9

  A facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides (PDIs) has been developed and the first two nonracemic chiral amphiphilic PDIs have been synthesized. The key building blocks, AB bifunctional 3,4,9, 10-perylenetetracarboxylic-3,4-anhydride-9, 10-imides, were prepared conveniently from enantiomerically pure alpha-amino acids, which were introduced as the steric and stereochemical controlling units. Such building blocks allow the incorporation of sterically and stereochemically controlled PDI moieties into both terminal and inner positions. (c) 2007 Elsevier Ltd. All rights reserved.