12b-methyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one | 24686-29-1

• 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: 12b-methyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one
• 英文别名: 12b-methyl-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one；12b-Methyl-1,2,3,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one
• CAS: 24686-29-1
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: LWDBHYFCXDXNBF-UHFFFAOYSA-N

物化性质

• 沸点：
  468.6±34.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  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

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。
• Gold‐catalyzed Rapid Construction of Nitrogen‐containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity
  作者：Jin Qiao、Xiuwen Jia、Pinyi Li、Xiaoyan Liu、Jingwei Zhao、Yu Zhou、Jiang Wang、Hong Liu、Fei Zhao

  DOI：10.1002/adsc.201801494

  日期：2019.3.15

  react with alkynoic acids (AAs) to achieve gold‐catalyzed highly selective cascade reactions to furnish novel indole‐fused skeletons. Furthermore, with this powerful gold catalytic system, a library of indole/pyrrole/thiophene/benzene/naphthalene/pyridine‐based nitrogen‐containing heterocyclic compounds (NCHCs) with scaffold diversity and molecular complexity was constructed rapidly using various amine

  1,3-未取代2-（1 H吲哚-2-基乙乙胺首次用于与炔酸（AAs）反应以实现金催化的高选择性级联反应，从而提供新颖的吲哚融合骨架。此外，借助这种功能强大的金催化系统，使用各种胺亲核试剂（AN）和苯胺/吡咯/噻吩/苯/萘/吡啶/吡啶基含氮杂环化合物（NCHCs）可以快速构建具有骨架多样性和分子复杂性的文库。各种AA作为基本要素。该通用规程具有出色的选择性，超宽的底物范围，易于获得的输入，良好的高收率，高的键形成效率和步骤经济性，因此可轻松有效地获得各种有价值的含氮杂环。
• Two‐in‐One Strategy for Palladium‐Catalyzed C−H Functionalization in Water
  作者：Huiying Zeng、Zemin Wang、Chao‐Jun Li

  DOI：10.1002/anie.201813391

  日期：2019.2.25

  Transition metal catalyzed C−H functionalizations have been developed as powerful methods for C−C bond formations. Directing groups, removable directing groups, traceless directing groups, and transient directing groups (TDGs) have been successfully used to improve the reaction efficiencies. For the development of greener and more sustainable methods, C−H functionalization using a TDG that also serves

  过渡金属催化的CH官能化已被开发为形成CC键的有力方法。导向基团，可移动的导向基团，无痕导向基团和瞬态导向基团（TDG）已被成功地用于提高反应效率。为了开发更绿色，更可持续的方法，研究了使用TDG的CH功能化，该TDG还可以用作水性溶剂中的试剂。使用酮在水中的钯催化的色胺类胺的CH-H官能化成功生成了四氢-β-咔啉，其四级碳中心位于C1。讨论了氘标记实验以提供对该机理的深入了解。吡啶的C2位也通过该策略成功地官能化。
• Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water
  作者：Xiuwen Jia、Pinyi Li、Xiaoyan Liu、Jiafu Lin、Yiwen Chu、Jinhai Yu、Jiang Wang、Hong Liu、Fei Zhao

  DOI：10.3390/molecules24050988

  日期：——

  scope. In addition, this is the first example of the generation of an indole/thiophene/pyrrole/pyridine/naphthalene/benzene-fused N-heterocycle library through gold catalysis in water from readily available materials. Notably, the discovery of antibacterial molecules from this library demonstrates its high quality and potential for the identification of active pharmaceutical ingredients.

  本研究描述了 AuPPh3Cl/AgSbF6 催化的胺亲核试剂和水中的炔酸之间的级联反应。这个过程以水作为唯一的副产物以高度经济的方式进行，并导致两个环的产生，同时在一次操作中形成三个新键。这种绿色级联工艺表现出有价值的特性，例如催化剂负载量低、产率高、成键效率高、选择性好、官能团耐受性好以及底物范围极其广泛。此外，这是在水中通过金催化从容易获得的材料生成吲哚/噻吩/吡咯/吡啶/萘/苯-稠合 N-杂环库的第一个例子。尤其，
• A Au(I)-Catalyzed <i>N</i>-Acyl Iminium Ion Cyclization Cascade
  作者：Ting Yang、Leonie Campbell、Darren J. Dixon

  DOI：10.1021/ja074550+

  日期：2007.10.1

  reported. The gold catalyst initially primes the alkynoic acid, via cyclization to an enol lactone, to react with a primary amine tethered to an electron rich heteroaromatic system. Then, via postulated Lewis acid assisted acidity, the Au(I) catalyst activates the amido ketone intermediate to undergo an N-acyl iminium ion cyclization. The reaction sequence is simple to perform, efficient, and broad in

  报道了从炔酸和伯胺到多环杂环产物的一锅 Au(I) 催化反应级联反应。金催化剂首先引发炔酸，通过环化生成烯醇内酯，与连接到富电子杂芳族系统的伯胺反应。然后，通过假定的路易斯酸辅助酸度，Au(I) 催化剂激活酰氨基酮中间体以进行 N-酰基亚胺离子环化。该反应序列操作简单、效率高，并且适用于各种复杂的杂环产物。