N-<2-Indolyl-(3)-ethyl>-3-acetyl-propionsaeure-amid | 17416-72-7

• 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: N-<2-Indolyl-(3)-ethyl>-3-acetyl-propionsaeure-amid
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]-4-oxopentanamide
• CAS: 17416-72-7
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: ZVKPTNSUPHPXML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  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
• 作为产物：
  描述：

  色胺 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 N-<2-Indolyl-(3)-ethyl>-3-acetyl-propionsaeure-amid
  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

• 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，
• USE OF CANTHIN-6-ONE AND ITS ANALOGS IN THE TREATMENT OF MYCOBACTERIA-LINKED PATHOLOGIES ( amended
  申请人：Fournet Alain Robert Francois Maxime

  公开号：US20110059977A1

  公开（公告）日：2011-03-10

  The present invention relates to the use, for the preparation of a medicament intended for the treatment or the prevention of pathologies linked to, or caused by mycobacteria, of at least one of the compounds of the following formula (I): in which B represents in particular a nitrogen atom, and R1, R2, R3, R4, R5, R6, R7 and R8 represent in particular a hydrogen atom.

  本发明涉及使用以下式(I)中至少一种化合物，用于制备用于治疗或预防与分支杆菌相关或由其引起的病理状况的药物，其中B特别代表氮原子，而R1、R2、R3、R4、R5、R6、R7和R8特别代表氢原子。
• Enantioselective Brønsted Acid-Catalyzed <i>N</i>-Acyliminium Cyclization Cascades
  作者：Michael E. Muratore、Chloe A. Holloway、Adam W. Pilling、R. Ian Storer、Graham Trevitt、Darren J. Dixon

  DOI：10.1021/ja9024885

  日期：2009.8.12

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.
• 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.