[((5S,10bR)-8-1,3-benzodioxol-5-yl-3-oxo-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carbonyl)amino]acetic acid

• 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: [((5S,10bR)-8-1,3-benzodioxol-5-yl-3-oxo-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carbonyl)amino]acetic acid
• 英文别名: 2-[[(5S,10bR)-8-(1,3-benzodioxol-5-yl)-3-oxo-2,5,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinoline-5-carbonyl]amino]acetic acid
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: ANPNVVNSLUPHRI-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Fmoc-甘氨酸 、 3.4-(亚甲基二氧基)苯硼酸 、 Fmoc-L-3-碘苯丙氨酸 、 3-[3-[(2-Methylpropan-2-yl)oxycarbonyl]-1,3-oxazinan-2-yl]propanoic acid 生成 [((5S,10bR)-8-1,3-benzodioxol-5-yl-3-oxo-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carbonyl)amino]acetic acid
  参考文献：
  名称：

  Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet–Spengler reactions

  摘要：

  Solid-supported masked peptide aldehydes containing 3- or 4-iodophenylalanine residues were subjected to Pd-catalyzed Suzuki cross-coupling reactions with arylboronic acids. The biarylalanines generated were applied in intramolecular N-acyliminium Pictet-Spengler reactions. In this way, a range of pharmacologically interesting aryl-substituted pyrroloisoquinolines was obtained in excellent purity (> 95%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.080

文献信息

• Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet–Spengler reactions
  作者：Thomas E. Nielsen、Sebastian Le Quement、Morten Meldal

  DOI：10.1016/j.tetlet.2005.09.080

  日期：2005.11

  Solid-supported masked peptide aldehydes containing 3- or 4-iodophenylalanine residues were subjected to Pd-catalyzed Suzuki cross-coupling reactions with arylboronic acids. The biarylalanines generated were applied in intramolecular N-acyliminium Pictet-Spengler reactions. In this way, a range of pharmacologically interesting aryl-substituted pyrroloisoquinolines was obtained in excellent purity (> 95%). (c) 2005 Elsevier Ltd. All rights reserved.