4-chloro-N-((4-chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl)benzenamine | 1251920-70-3

• 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: 4-chloro-N-((4-chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl)benzenamine
• 英文别名: N-((5-bromo-1H-indol-3-yl)(4-methoxyphenyl)methyl)-N-methylaniline；N-[(5-bromo-1H-indol-3-yl)-(4-methoxyphenyl)methyl]-N-methylaniline
• CAS: 1251920-70-3
• 化学式: C₂₃H₂₁BrN₂O
• 分子量: 421.337
• InChiKey: LTMDZKARKGINDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-N-((4-chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl)benzenamine 在 吡啶 、 水 、 碘 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Thioctic acid modification of oligonucleotides using an H-phosphonate

  摘要：

  The H-phosphonate of a derivative of thioctic acid (TA) was synthesised and used to introduce a disulfide moiety at the 5'-end of oligonucleotides. This method overcomes the difficulties experienced with the phosphoramidite approach when employing a cyclic disulfide in the starting alcohol. The disulfide-modified oligonucleotides are subsequently used in metallic nanoparticle (Au and Ag) and surface functionalisation for sensitive, sequence specific analytical detection strategies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.107
• 作为产物：
  描述：

  、 在 吡啶 、 三甲基乙酰氯 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 4-chloro-N-((4-chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl)benzenamine
  参考文献：
  名称：

  Thioctic acid modification of oligonucleotides using an H-phosphonate

  摘要：

  The H-phosphonate of a derivative of thioctic acid (TA) was synthesised and used to introduce a disulfide moiety at the 5'-end of oligonucleotides. This method overcomes the difficulties experienced with the phosphoramidite approach when employing a cyclic disulfide in the starting alcohol. The disulfide-modified oligonucleotides are subsequently used in metallic nanoparticle (Au and Ag) and surface functionalisation for sensitive, sequence specific analytical detection strategies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.107

文献信息

• One-Pot Synthesis of 3-[(<i>N</i>-Alkylanilino)(aryl)methyl]indoles via a Transition Metal Assisted Three-Component Condensation at Room Temperature
  作者：Goutam Brahmachari、Suvankar Das

  DOI：10.1002/jhet.1909

  日期：2014.8

  A simple and highly efficient protocol for the one-pot synthesis of a series of 3-[(N-alkylanilino)(aryl)methyl]indoles has been developed based on low-cost and environmentally benign zirconium oxychloride octahydrate and copper chloride dihydrate catalysts via three-component condensation between indoles, aromatic aldehydes, and N-alkylanilines at room temperature under neat condition. Mild reaction

  基于低成本，环境友好的八水合氯氧化锆和二水合氯化铜催化剂，开发了一种简单高效的协议，可以一锅合成一系列3-[（N-烷基苯胺基）（芳基）甲基]吲哚。室温，纯净条件下，吲哚，芳族醛和N-烷基苯胺之间的三组分缩合反应。温和的反应条件，操作简便，原子经济性高，在相对较短的反应时间内具有良好的收率，使用低成本和环境友好的催化剂是该协议的主要特征。
• PANI-HBF₄: A Reusable Polymer-Based Solid Acid Catalyst for Three-Component, One-Pot Synthesis of 3-Substituted Amino Methyl Indoles Under Solvent-Free Conditions
  作者：Chebrolu Lavanya Devi、Vaidya Jayathirtha Rao、Srinivasan Palaniappan

  DOI：10.1080/00397911.2010.542535

  日期：2012.6

  Abstract A simple, fast, efficient, high-yielding, and green process is developed for one-pot, three-component synthesis of 3-substituted amino methyl indoles under solvent-free conditions using polyaniline salt as polymer-based reusable solid acid catalyst at room temperature. The advantages of polyaniline salt catalyst are ease of synthesis and handling, low cost, versatality, and recyclability.

  摘要 以聚苯胺盐为聚合物基可重复使用的固体酸催化剂，在无溶剂条件下，开发了一种简单、快速、高效、高产、绿色的三组分一锅法合成3-取代氨基甲基吲哚的方法。室内温度。聚苯胺盐催化剂的优点是易于合成和处理、低成本、通用性和可回收性。图形概要
• Catalyst-free, ethylene glycol promoted one-pot three component synthesis of 3-amino alkylated indoles via Mannich-type reaction
  作者：U. Chinna Rajesh、Rohit Kholiya、V. Satya Pavan、Diwan S. Rawat

  DOI：10.1016/j.tetlet.2014.03.112

  日期：2014.4

  A highly efficient and sustainable approach for the multi-component synthesis of biologically important 3-amino alkylated indoles has been investigated via Mannich-type reaction under catalyst-free, ethylene glycol as a recyclable promoting medium. The wide applicability of the present method was examined with various substrates viz substituted aldehydes, indoles and secondary amines. This method will be useful for a large scale synthesis of 3-amino alkylated indoles without the use of column chromatography. The present method provides higher environmental compatibility and sustainability factors such as smaller E-factor (0.433) and higher atom-economy (AE = 93.3%). (C) 2014 Elsevier Ltd. All rights reserved.
• Bromodimethylsulfonium bromide (BDMS)-catalyzed multicomponent synthesis of 3-aminoalkylated indoles
  作者：Deepak K. Yadav、Rajesh Patel、Vishnu P. Srivastava、Geeta Watal、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2010.08.065

  日期：2010.10

  Bromodimethylsulfonium bromide (BDMS)-catalyzed three-component coupling reaction between indoles, aldehydes, and N-alkylanilines is reported to access substituted 3-aminoalkylated indoles at room temperature in high yields (82-96%) within 1.5-3.5 h. The salient features of this protocol are the simplicity of the procedure, the ready accessibility of the catalyst, its cost effectiveness, and higher yields in relatively short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.
• 3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities
  作者：V. Kameshwara Rao、Bhupender S. Chhikara、Amir Nasrolahi Shirazi、Rakesh Tiwari、Keykavous Parang、Anil Kumar

  DOI：10.1016/j.bmcl.2011.05.010

  日期：2011.6

  An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf)(3)-SiO2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 mu M. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC50 values of 50.6 and 58.3 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.