2-(1,3-dioxooctahydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(1,3-dioxooctahydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid
• 英文别名: 2-(1,3-dioxooctahydro-2H-isoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid；2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: JIGBTNBWQQOTLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  六氢苯酐 、 DL-色氨酸 在 吡啶 作用下， 反应 12.0h， 以92%的产率得到2-(1,3-dioxooctahydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid
  参考文献：
  名称：

  Cyclomaltooligosaccharide-assisted spectroscopic discrimination of phthalimido-derived amino acids through the formation of molecular aggregates

  摘要：

  Spectroscopic evidence was used to demonstrate the formation of molecular associates in an aqueous solution of phthalimido tryptophan. These molecular associates are loosely formed through 7r-n aromatic stacking, properties that are not sufficient to cause NMR spectroscopic enantiomeric discrimination. A cyclomaltooligosaccharide with a larger cavity, such as cyclomaltooctaose (gamma-cyclodextrin), is capable of forming a ternary complex with these molecular associates and enhances pi-pi aromatic stacking interactions, resulting in NMR enantiomeric discrimination. Electrospray-ionization mass spectroscopy (ESIMS) and NOESY two-dimensional NMR spectroscopic methods were used to study these complexes. Association constants and thermodynamic data for these cyclomaltooligosaccharide complexes were also estimated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.09.013

文献信息

• Cyclomaltooligosaccharide-assisted spectroscopic discrimination of phthalimido-derived amino acids through the formation of molecular aggregates
  作者：Branko S. Jursic、Paresh K. Patel

  DOI：10.1016/j.carres.2006.09.013

  日期：2006.12

  Spectroscopic evidence was used to demonstrate the formation of molecular associates in an aqueous solution of phthalimido tryptophan. These molecular associates are loosely formed through 7r-n aromatic stacking, properties that are not sufficient to cause NMR spectroscopic enantiomeric discrimination. A cyclomaltooligosaccharide with a larger cavity, such as cyclomaltooctaose (gamma-cyclodextrin), is capable of forming a ternary complex with these molecular associates and enhances pi-pi aromatic stacking interactions, resulting in NMR enantiomeric discrimination. Electrospray-ionization mass spectroscopy (ESIMS) and NOESY two-dimensional NMR spectroscopic methods were used to study these complexes. Association constants and thermodynamic data for these cyclomaltooligosaccharide complexes were also estimated. (c) 2006 Elsevier Ltd. All rights reserved.