1-benzyl-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indole | 1450892-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-benzyl-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indole
• 英文别名: 1-Benzyl-2-(4-methoxyphenyl)-4,5,6,7-tetrahydroindole；1-benzyl-2-(4-methoxyphenyl)-4,5,6,7-tetrahydroindole
• CAS: 1450892-99-5
• 化学式: C₂₂H₂₃NO
• 分子量: 317.431
• InChiKey: BWPDZQXJMXNZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-乙炔基-7-氧杂双环[4.1.0]庚烷 在 copper(l) iodide 、 lithium perchlorate 、 二乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙腈 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 生成 1-benzyl-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indole
  参考文献：
  名称：

  通过连续 Sonogashira 偶联/Pd 介导的 5-endo-dig 环化合成 4,5,6,7-四氢-1H-吲哚衍生物

  摘要：

  开发了导致 2-芳基-4,5,6,7-四氢吲哚的一锅 Sonogashira 交叉偶联/5-endo-dig 环化程序。这种短（仅从市售化合物中提取两个步骤）序列避免了苛刻的条件和昂贵的催化剂。我们的程序对一系列官能团（氨基、硝基、羧基、氰基、羟基和溴）具有高度耐受性。以克级规模合成了 21 种四氢吲哚家族，产率良好至极好，这表明该反应的一般特征和可扩展性。这种方法允许在 C2 位置（通过 ArI 的变化）和氮原子（通过 RNH2 的变化，包括手性部分）获得带有杂项取代基的吲哚。

  DOI：

  10.1002/ejoc.201201417

文献信息

• Gold(I)-Catalyzed Synthesis of Highly Substituted 1,4-Dicarbonyl Derivatives via Sulfonium [3,3]-Sigmatropic Rearrangement
  作者：Weiping Zhou、Arnaud Voituriez

  DOI：10.1021/acs.orglett.0c04023

  日期：2021.1.1

  2-substituted 4-oxo-4-arylbutanal derivatives from commercially available or easily accessible alkynes and vinylsulfoxide substrates has been developed. Extension of the methodology to the use of 1-cycloalkenyl sulfoxides allowed the facile synthesis of five-, six-, and seven-membered-ring cycloalkyl-1-one backbone. Subsequently, the tetrahydrocycloalkyl[b]pyrrole derivatives, which are found in many active

  已经开发了一种有效且直接的金催化方案，用于从市售或易于获得的炔烃和乙烯基亚砜底物合成2-取代的4-氧代-4-芳基丁醛衍生物。方法的扩展到使用1-环烯基亚砜使得可以容易地合成五，六和七元环的环烷基-1-一主链。随后，以良好的产率分离出了在许多活性药物成分中发现的四氢环烷基[ b ]吡咯衍生物。机理研究突出了在此过程中a中间体的[3,3]-σ重排。
• Synthesis of 4,5,6,7-Tetrahydro-1<i>H</i>-indole Derivatives Through Successive Sonogashira Coupling/Pd-Mediated 5-<i>endo</i>-<i>dig</i>Cyclization
  作者：Ivan A. Andreev、Dmitry S. Belov、Alexander V. Kurkin、Marina A. Yurovskaya

  DOI：10.1002/ejoc.201201417

  日期：2013.2

  A one-pot Sonogashira cross-coupling/5-endo-dig cyclization procedure leading to 2-aryl-4,5,6,7-tetrahydroindoles was developed. This short (only two steps from commercially available compounds) sequence avoids harsh conditions and expensive catalysts. Our procedure is highly tolerant to a range of functional groups (amino, nitro, carboxy, cyano, hydroxy, and bromo). A family of 21 tetrahydroindoles

  开发了导致 2-芳基-4,5,6,7-四氢吲哚的一锅 Sonogashira 交叉偶联/5-endo-dig 环化程序。这种短（仅从市售化合物中提取两个步骤）序列避免了苛刻的条件和昂贵的催化剂。我们的程序对一系列官能团（氨基、硝基、羧基、氰基、羟基和溴）具有高度耐受性。以克级规模合成了 21 种四氢吲哚家族，产率良好至极好，这表明该反应的一般特征和可扩展性。这种方法允许在 C2 位置（通过 ArI 的变化）和氮原子（通过 RNH2 的变化，包括手性部分）获得带有杂项取代基的吲哚。
• Discovery of the 2-phenyl-4,5,6,7-Tetrahydro-1H-indole as a novel anti-hepatitis C virus targeting scaffold
  作者：Ivan A. Andreev、Dinesh Manvar、Maria Letizia Barreca、Dmitry S. Belov、Amartya Basu、Noreena L. Sweeney、Nina K. Ratmanova、Evgeny R. Lukyanenko、Giuseppe Manfroni、Violetta Cecchetti、David N. Frick、Andrea Altieri、Neerja Kaushik-Basu、Alexander V. Kurkin

  DOI：10.1016/j.ejmech.2015.04.022

  日期：2015.5

  Although all-oral direct-acting antiviral (DAA) therapy for hepatitis C virus (HCV) treatment is now a reality, today's HCV drugs are expensive, and more affordable drugs are still urgently needed. In this work, we report the identification of the 2-phenyl-4,5,6,7-Tetrahydro-1H-indole chemical scaffold that inhibits cellular replication of HCV genotype 1b and 2a subgenomic replicons. The anti-HCV genotype lb and 2a profiling and effects on cell viability of a selected representative set of derivatives as well as their chemical synthesis are described herein. The most potent compound 39 displayed EC50 values of 7.9 and 2.6 mu M in genotype lb and 2a, respectively. Biochemical assays showed that derivative 39 had no effect on HCV NS5B polymerase, NS3 helicase, IRES mediated translation and selected host factors. Thus, future work will involve both the chemical optimization and target identification of 2-phenyl-4,5,6,7-Tetrahydro-1H-indoles as new anti-HCV agents. (C) 2015 Elsevier Masson SAS. All rights reserved.
• A Small-Molecule Inhibitor of Prion Replication and Mutant Prion Protein Toxicity
  作者：Tania Massignan、Valeria Sangiovanni、Silvia Biggi、Claudia Stincardini、Saioa R. Elezgarai、Giulia Maietta、Ivan A. Andreev、Nina K. Ratmanova、Dmitry S. Belov、Evgeny R. Lukyanenko、Grigory M. Belov、Maria Letizia Barreca、Andrea Altieri、Alexander V. Kurkin、Emiliano Biasini

  DOI：10.1002/cmdc.201700302

  日期：2017.8.22

  Into the fold: Prion diseases are neurodegenerative disorders characterized by the accumulation in the brain of a self-replicating, misfolded isoform (PrPSc ) of the cellular prion protein (PrPC ). No therapies are available for these pathologies. We capitalized on previously described cell-based assays to screen a library of small molecules, and identified 55, a compound capable of counteracting both

  折叠：Pri病毒疾病是神经退行性疾病，其特征是细胞病毒蛋白（PrPC）的自我复制，错误折叠的同工型（PrPSc）在大脑中积累。没有针对这些病理的疗法。我们利用先前描述的基于细胞的分析方法来筛选小分子文库，并鉴定出55种能够抵消病毒复制和毒性的化合物。化合物55可以代表开发病毒疾病的全新疗法的起点。