(5S,11bS)-5-(hydroxymethyl)-11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one | 546128-79-4

• 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: (5S,11bS)-5-(hydroxymethyl)-11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one
• 英文别名: (5S,11bS)-5-hydroxymethyl-11b-methyl-1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-one；(5S,11bS)-5-(hydroxymethyl)-11b-methyl-2,5,6,11-tetrahydro-1H-indolizino[8,7-b]indol-3-one
• CAS: 546128-79-4
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: IOEPTQDNFBNROJ-QFYYESIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,11bS)-5-(hydroxymethyl)-11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one 在 palladium on activated charcoal 反式-双(三苯基膦)合氯化羰基铑(Ⅰ) 、 氢气 、 红铝 、 2-碘酰基苯甲酸 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 、 xylene 为溶剂， 反应 212.0h， 生成 (S)-11b-Methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
  参考文献：
  名称：

  Stereoselective synthesis of the indolizinoindole ring system

  摘要：

  We report a novel, facile and stereoselective approach to the indolizino[8,7-b]indole ring system from a readily available, non-racemic chiral template. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00250-8
• 作为产物：
  描述：

  L-色氨醇 在 咪唑 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 102.0h， 生成 (5S,11bS)-5-(hydroxymethyl)-11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-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

文献信息

• Racemic and diastereoselective construction of indole alkaloids under solvent- and catalyst-free microwave-assisted Pictet–Spengler condensation
  作者：Mouhamad Jida、Olivier-Mohamad Soueidan、Benoit Deprez、Guillaume Laconde、Rebecca Deprez-Poulain

  DOI：10.1039/c2gc16596a

  日期：——

  An environment-friendly high-yielding method for the racemic and asymmetric diastereoselective preparation of indole alkaloids via Pictet–Spengler reaction is reported. The reaction proceeds with short reaction times under solvent-free and microwave-irradiation conditions.

  报道了一种环境友好且高产率的吲哚生物碱制备方法，通过Pictet-Spengler反应实现外消旋和不对称对映选择性合成。该反应在无溶剂和微波辐射条件下进行，反应时间短。
• Diverse synthesis of natural product inspired fused and spiro-heterocyclic scaffolds via ring distortion and ring construction strategies
  作者：Chandramohan Bathula、Poonam Dangi、Santanu Hati、Rahul Agarwal、Parthapratim Munshi、Ashutosh Singh、Shailja Singh、Subhabrata Sen

  DOI：10.1039/c5nj01858g

  日期：——

  A toolkit of indole scaffolds inspired from natural products.

  一种受自然产物启发的吲哚骨架工具包。
• 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.
• Stereoselective synthesis of the indolizinoindole ring system
  作者：Steven M. Allin、Christopher I. Thomas、James E. Allard、Matthew Duncton、Mark R.J. Elsegood、Mark Edgar

  DOI：10.1016/s0040-4039(03)00250-8

  日期：2003.3

  We report a novel, facile and stereoselective approach to the indolizino[8,7-b]indole ring system from a readily available, non-racemic chiral template. (C) 2003 Elsevier Science Ltd. All rights reserved.