3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole | 14008-96-9

• 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: 3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole
• 英文别名: 3-(2-Pyrrolidinylethyl)indole；3-(2-pyrrolidin-1-ylethyl)-1H-indole
• CAS: 14008-96-9
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: CVTZCBLFHNGYDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C (sublm)
• 沸点：
  371.6±17.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole 在 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 32.0h， 生成 1-methyl-1-(2-(1-(3-methylbut-2-enyl)-1H-indol-3-yl)ethyl)pyrrolidinium iodide
  参考文献：
  名称：

  Synthesis and evaluation of N1-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands

  摘要：

  In this study thirty-three novel indole derivatives were designed and synthesized based on the structure of deformylflustrabromine B (1), a metabolite isolated from the marine bryozoan Flustra foliacea L. The syntheses were carried out using standard methodologies and in good yields. The molecules were tested for their affinities for the alpha 4 beta 2*, alpha 3 beta 4*, alpha 7* and (alpha 1)(2)beta 1 gamma delta nicotinic acetylcholine receptor (nAChR) sub-types. Binding assays showed that, among these ligands, compound 7c exhibited the highest affinity with K-i = 136.1, 93.9 and 862.4 nM for the alpha 4 beta 2*, alpha 3 beta 4*, and alpha 7* nAChRs subtypes, respectively. These results indicated that the indole core might be a useful scaffold for the development of new potent and selective nAChR ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.050
• 作为产物：
  描述：

  1-(1H-indol-3-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione 在 lithium aluminium tetrahydride 作用下， 生成 3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole
  参考文献：
  名称：

  Barlow; Khan, British Journal of Pharmacology and Chemotherapy, 1959, vol. 14, p. 99,101

  摘要：

  DOI：

文献信息

• Engineering an Enantioselective Amine Oxidase for the Synthesis of Pharmaceutical Building Blocks and Alkaloid Natural Products
  作者：Diego Ghislieri、Anthony P. Green、Marta Pontini、Simon C. Willies、Ian Rowles、Annika Frank、Gideon Grogan、Nicholas J. Turner

  DOI：10.1021/ja4051235

  日期：2013.7.24

  catalytic methods for the production of enantiomerically pure chiral amines is a key challenge facing the pharmaceutical and fine chemical industries. This challenge is highlighted by the estimate that 40-45% of drug candidates contain a chiral amine, fueling a demand for broadly applicable synthetic methods that deliver target structures in high yield and enantiomeric excess. Herein we describe the development

  开发用于生产对映异构纯手性胺的经济高效且可持续的催化方法是制药和精细化工行业面临的关键挑战。据估计，40-45% 的候选药物含有手性胺，这突显了这一挑战，这推动了对以高产率和对映体过量提供目标结构的广泛适用的合成方法的需求。在此，我们描述了来自黑曲霉 (MAO-N) 的单胺氧化酶变体“工具箱”的开发和应用，该变体显示出显着的底物范围和对空间要求基序的耐受性，包括一个新变体，它对含有以下物质的底物表现出高活性和对映选择性氨基二苯甲烷（二苯甲基胺）模板。通过将合理的结构导向工程与高通量筛选相结合，可以扩大 MAO-N 的底物范围以适应含有大量芳基取代基的胺底物。这些工程化的 MAO-N 生物催化剂已应用于去消旋反应，用于高效不对称合成仿制药活性药物成分索利那新和左西替利嗪以及天然产物 (R)-coniine、(R)-eleagnine 和 (R)-leptaflorine . 我们还报告了一种新的
• SUBSTITUTED HETEROARYL DERIVATIVES
  申请人：Zemolka Saskia

  公开号：US20100009986A1

  公开（公告）日：2010-01-14

  The invention relates to substituted heteroaryl derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted heteroaryl derivatives for producing medicaments.

  这项发明涉及替代杂环芳基衍生物，涉及其生产方法，含有该化合物的药物以及利用替代杂环芳基衍生物生产药物的用途。
• A facile procedure for synthesis of 3-[2-(N,N-dialkylamino)ethyl]-3-fluorooxindoles by direct fluorination of N,N-dialkyltryptamines
  作者：Takayuki Seki、Tomoya Fujiwara、Yoshio Takeuchi

  DOI：10.1016/j.jfluchem.2010.12.014

  日期：2011.3

  A practical procedure for the synthesis of 3-fluorooxindole derivatives having basic amine moieties was developed, which involves Selectfluor™-mediated oxidative fluorination of N,N-dialkyltryptamines in the presence of Lewis acid. This procedure was applied to an antimigraine drug, rizatriptan, to afford the corresponding 3-fluorooxindole, which is a potential fluorine-containing drug candidate.

  已开发出一种合成具有碱性胺基团的3-氟羟吲哚衍生物的实用方法，该方法涉及在路易斯酸存在下，Selectfluor TM介导的N，N-二烷基色胺的氧化氟化。将该方法应用于抗偏头痛药物利扎曲普坦（rizatriptan），得到相应的3-氟羟吲哚，其是潜在的含氟药物候选物。
• Ruthenium Complex-Catalyzed N-Heterocyclization. Syntheses of<i>N</i>-Substituted Pyrroles and Pyrrolidines from 1,4-Diols and Primary Amines
  作者：Yasushi Tsuji、Yasuharu Yokoyama、Keun-Tae Huh、Yoshihisa Watanabe

  DOI：10.1246/bcsj.60.3456

  日期：1987.9

  2-Butyne-1,4-diol reacts with aliphatic amines in the presence of a catalytic amount of [RuCl2(PPh3)3] at 150 °C to give N-alkylpyrroles in good yields. 1,4-Butanediol reacts with aromatic or aliphatic amines to give N-substituted pyrrolidines in excellent yields; [RuCl2(PPh3)3] and [RuCl3·nH2O–3PBu3] are the best catalysts for aromatic and aliphatic amines, respectively. The reaction of 2-butene-1,4-diol with alkyl amines gives a 1:1 mixture of N-substituted pyrroles and pyrrolidines in high yield.

  2-丁炔-1,4-二醇在150°C下与脂肪胺在催化量的[RuCl2(PPh3)3]存在下反应，生成N-烷基吡咯，产率良好。1,4-丁二醇与芳香胺或脂肪胺反应，生成N-取代的吡咯烷，产率极高；[RuCl2(PPh3)3]和[RuCl3·nH2O–3PBu3]分别是芳香和脂肪胺的最佳催化剂。2-丁烯-1,4-二醇与烷基胺反应产生1:1的N-取代吡咯和吡咯烷混合物，且产率较高。
• Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts
  作者：Caroline Grundke、Rodrigo C. Silva、Winald R. Kitzmann、Katja Heinze、Kleber T. de Oliveira、Till Opatz

  DOI：10.1021/acs.joc.1c03101

  日期：2022.5.6

  light-harvesting porphyrins, chlorins, and mainly bacteriochlorins and are also known for being efficient and affordable near-infrared light absorbers as well as triplet sensitizers for the production of singlet oxygen. Although having been neglected for a long time in synthetic organic chemistry due to their low solubility and high tendency toward aggregation, their unique photophysical properties and chemical

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