11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one | 727-45-7

• 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: 11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one
• 英文别名: 11b-Methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one；11b-methyl-2,5,6,11-tetrahydro-1H-indolizino[8,7-b]indol-3-one
• CAS: 727-45-7
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: YZCPZTYKWQSAJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one 在 1,3-二溴-5,5-二甲基海因 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到(1'R)-7a'-methyl-2',3',7',7a'-tetrahydrospiro[indoline-3,1'-pyrrolizine]-2,5'(6'H)-dione
  参考文献：
  名称：

  Diverse synthesis of natural product inspired fused and spiro-heterocyclic scaffolds via ring distortion and ring construction strategies

  摘要：

  一种受自然产物启发的吲哚骨架工具包。

  DOI：

  10.1039/c5nj01858g
• 作为产物：
  描述：

  N-<2-Indolyl-(3)-ethyl>-3-acetyl-propionsaeure-amid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到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。
• From Simple Furans to Complex Nitrogen-Bearing Aromatic Polycycles by Means of a Flexible and General Reaction Sequence Initiated by Singlet Oxygen
  作者：Dimitris Kalaitzakis、Tamsyn Montagnon、Eirini Antonatou、Nuria Bardají、Georgios Vassilikogiannakis

  DOI：10.1002/chem.201301571

  日期：2013.7.29

  All‐in‐one: A new and general one‐pot reaction sequence initiated by singlet oxygen that transforms simple furan substrates into complex nitrogen‐bearing aromatic polycycles having all the structural features of a number of important natural products (for example, the erythrina alkaloids; see scheme, RB=rose Bengal) is reported. The reaction sequence itself uses mild conditions and has wide functional

  多合一：由单线态氧引发的新的通用单锅反应序列，可将简单的呋喃底物转化为具有许多重要天然产物的所有结构特征的复杂的含氮芳族多环化合物（例如赤藓生物碱） ；参见方案，报道RB =玫瑰孟加拉）。反应序列本身使用温和的条件，并具有宽泛的官能团耐受性。
• 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。
• 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，
• Indole fused heterocyclic diuretic compounds
  申请人：American Home Products Corporation

  公开号：US03943148A1

  公开（公告）日：1976-03-09

  Substituted 1,2,4,5,6,7,8,9-octahydro-3H-azecino[5,4-b]-indoles and substituted 1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]-indoles are prepared by cleavage of the corresponding quaternary alkyl iodide salts with lithium in liquid ammonia. The products possess diuretic activity.

  通过在液氨中使用锂对应的季铵碘化物盐进行裂解，制备了取代的1,2,4,5,6,7,8,9-八氢-3H-氮杂环[5,4-b]-吲哚和取代的1,2,3,4,5,6,7,8-八氢-氮杂环[5,4-b]-吲哚。这些产物具有利尿活性。