δ-Oxo-capronsaeure-tryptamid | 93537-77-0

• 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: δ-Oxo-capronsaeure-tryptamid
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]-5-oxohexanamide
• CAS: 93537-77-0
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: RMZXRVIQHCQVKS-UHFFFAOYSA-N

物化性质

• 沸点：
  564.8±40.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  δ-Oxo-capronsaeure-tryptamid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到12b-methyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one
  参考文献：
  名称：

  A practical approach to the fused β-carboline system. Asymmetric synthesis of indolo[2,3-a]indolizidinones via a diastereoselective intramolecular α-amidoalkylation reaction

  摘要：

  Fused beta-carboline systems, as indolo[2,3-a]indolizidinones, indolo[2,3-a]quinolizidinones, their 2-oxa analogues, and benzo[a]indolo[2,3-a]indolizidinones are prepared efficiently via an RLi addition-N-acyliminium ion cyclisation sequence on readily available imides. In an enantioselective variant of these alpha-amidoalkylation reactions, the addition of MeLi to a chiral non-racemic imide derived from tryptophan yielded an oxo amide, which was cyclised diastereoselectively upon treatment with BF3.OEt2, to afford 5,11b-trans-indoloindolizidinone in moderate yield and high ee (99%). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.097
• 作为产物：
  描述：

  戊二酸酐 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 δ-Oxo-capronsaeure-tryptamid
  参考文献：
  名称：

  A practical approach to the fused β-carboline system. Asymmetric synthesis of indolo[2,3-a]indolizidinones via a diastereoselective intramolecular α-amidoalkylation reaction

  摘要：

  Fused beta-carboline systems, as indolo[2,3-a]indolizidinones, indolo[2,3-a]quinolizidinones, their 2-oxa analogues, and benzo[a]indolo[2,3-a]indolizidinones are prepared efficiently via an RLi addition-N-acyliminium ion cyclisation sequence on readily available imides. In an enantioselective variant of these alpha-amidoalkylation reactions, the addition of MeLi to a chiral non-racemic imide derived from tryptophan yielded an oxo amide, which was cyclised diastereoselectively upon treatment with BF3.OEt2, to afford 5,11b-trans-indoloindolizidinone in moderate yield and high ee (99%). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.097

文献信息

• A practical approach to the fused β-carboline system. Asymmetric synthesis of indolo[2,3-a]indolizidinones via a diastereoselective intramolecular α-amidoalkylation reaction
  作者：Ainhoa Ardeo、Eva Garcı́a、Sonia Arrasate、Esther Lete、Nuria Sotomayor

  DOI：10.1016/j.tetlet.2003.09.097

  日期：2003.11.10

  Fused beta-carboline systems, as indolo[2,3-a]indolizidinones, indolo[2,3-a]quinolizidinones, their 2-oxa analogues, and benzo[a]indolo[2,3-a]indolizidinones are prepared efficiently via an RLi addition-N-acyliminium ion cyclisation sequence on readily available imides. In an enantioselective variant of these alpha-amidoalkylation reactions, the addition of MeLi to a chiral non-racemic imide derived from tryptophan yielded an oxo amide, which was cyclised diastereoselectively upon treatment with BF3.OEt2, to afford 5,11b-trans-indoloindolizidinone in moderate yield and high ee (99%). (C) 2003 Elsevier Ltd. All rights reserved.