1-(4-chlorophenyl)-2-phenyl-1H-indole | 1259659-02-3

• 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: 1-(4-chlorophenyl)-2-phenyl-1H-indole
• 英文别名: 1-(4-Chlorophenyl)-2-phenylindole；1-(4-chlorophenyl)-2-phenylindole
• CAS: 1259659-02-3
• 化学式: C₂₀H₁₄ClN
• 分子量: 303.791
• InChiKey: VPDNXNWZHXOUFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-phenyl-1H-indole 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 N-[2-二(1-金刚烷)磷苯基]吗啉 、 一水合肼 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid

  摘要：

  N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.022
• 作为产物：
  描述：

  氯苯 在 m-chloroperoxybenzoic acid 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 生成 1-(4-chlorophenyl)-2-phenyl-1H-indole
  参考文献：
  名称：

  从Diaryliodonium盐和2-炔基苯胺中获得吲哚衍生物的途径

  摘要：

  已经开发了一种从2-炔基苯胺和二芳基碘鎓盐制备1，2-二取代的吲哚的有效，环保且操作简单的方法。该反应在无金属的条件下顺利进行。得到的产物可以用钯催化的DMSO转移到3，3′-二吲哚基甲烷中。同位素标记实验表明3,3'-二吲哚基甲烷中的亚甲基衍生自DMSO。对于28个实例，以高达90％的产率获得了多种吲哚。

  DOI：

  10.1021/acs.joc.6b00106

文献信息

• Efficient palladium-catalyzed synthesis of substituted indoles employing a new (silanyloxyphenyl)phosphine ligand
  作者：Christopher B. Lavery、Robert McDonald、Mark Stradiotto

  DOI：10.1039/c2cc33071g

  日期：——

  The new and easily prepared OTips-DalPhos ligand (L1) offers broad substrate scope at relatively low loadings in the palladium-catalyzed C-N cross-coupling/cyclization of o-alkynylhalo(hetero)arenes with primary amines, affording indoles and related heterocyclic derivatives in high yield.

  新型且易于制备的OTips-DalPhos配体（L1）在钯催化的邻炔基卤代（杂）芳烃与伯胺的CN交叉偶联/环化反应中以相对较低的负载量提供了较宽的底物范围，从而提供了吲哚和相关的杂环衍生物高产。
• [EN] SILANYLOXYARYL PHOSPHINE LIGAND AND USES THEREOF IN C-N CROSS-COUPLING<br/>[FR] LIGAND À LA SILANYLOXYARYLE PHOSPHINE ET SES UTILISATIONS DANS LE COUPLAGE CROISÉ C-N
  申请人：UNIV DALHOUSIE

  公开号：WO2013159229A1

  公开（公告）日：2013-10-31

  The present invention pertains to silanyloxyaryl phosphine ligands of formula (I) and their uses with transition metal catalyst precursors for organic synthesis reactions. More particularly, the present invention pertains to the use of silanyloxyaryl phosphine ligands and with transition metal catalyst precursors in C-N cross-coupling reactions.

  本发明涉及式(I)的硅氧基芳基膦配体及其与过渡金属催化剂前体在有机合成反应中的用途。更具体地说，本发明涉及在C-N交叉偶联反应中使用硅氧基芳基膦配体和过渡金属催化剂前体的用途。
• One-Pot Approach to 1,2-Disubstituted Indoles via Cu(II)-Catalyzed Coupling/Cyclization under Aerobic Conditions and Its Application for the Synthesis of Polycyclic Indoles
  作者：Jilong Gao、Yingying Shao、Jiaoyan Zhu、Jiaqi Zhu、Hui Mao、Xiaoxia Wang、Xin Lv

  DOI：10.1021/jo501250u

  日期：2014.10.3

  derivatives were efficiently and facilely synthesized from 2-alkynylanilines and boronic acids. 2-(2-Bromoaryl)-1-aryl-1H-indoles, which were selectively generated in one pot under the Cu catalysis, afforded the indolo[1,2-f]phenanthridines via Pd-catalyzed intramolecular direct C(sp2)–H arylation. The one-pot tandem approaches to the polycyclic indole derivatives were also successfully achieved.

  通过Cu（II）催化的多米诺骨牌偶联/环化工艺已经开发出一种简单的1,2-二取代的吲哚组装体。在有氧条件下，可以从2-炔基苯胺和硼酸有效地合成各种1,2-二取代的吲哚衍生物。在铜催化下在一锅中选择性生成的2-（2-溴芳基）-1-芳基-1 H-吲哚通过Pd催化的分子内直接C（sp 2）提供吲哚[1,2- f ]菲啶）–芳基化。一锅串联方法也成功地实现了多环吲哚衍生物。
• “On-Water,” Microwave-Assisted, Pd-Catalyzed Synthesis of Indoles from Imines and o-Difunctionalized Arenes
  作者：José Barluenga、Agustín Jiménez-Aquino、Fernando Aznar、Carlos Valdés

  DOI：10.1002/chem.201000753

  日期：——

  Regioselectively substituted indoles are prepared by a Pd‐catalyzed CC/CN bond‐forming sequence from imines and o‐dihaloarenes or o‐haloarene sulfonates. The heterogeneous reaction as a suspension in water and under microwave heating offers important advantages in comparison with the conventional reaction in an organic solvent, among them, operational simplicity, the employment of KOH solutions instead

  区域选择性取代的吲哚通过Pd催化的C中制备 C / C  N键形成序列从亚胺和ö -dihaloarenes或ö -haloarene磺酸盐。与在有机溶剂中的常规反应相比，在水中和微波加热下作为悬浮液的非均相反应具有重要的优势，其中包括操作简便，使用KOH溶液代替醇盐以及显着减少反应时间。
• CNT-CuO catalyzed C–N bond formation for N-arylation of 2-phenylindoles
  作者：Jeongah Lim、Ji Dang Kim、Hyun Chul Choi、Sunwoo Lee

  DOI：10.1016/j.jorganchem.2019.120970

  日期：2019.12

  Carbon nanotube-copper oxide (CNT-CuO) nanocomposites were prepared by depositing CuO nanoparticles onto functionalized CNT surfaces. The structure and elemental content of CNT-CuO were characterized using transmission electron microscopy, X-ray diffraction, and Auger electron spectroscopy. The prepared CNT-CuO was subsequently employed as a catalyst for the coupling reaction of 2-phenylindole with aryl iodides to provide the desired N-aryl 2-phenylindoles in good yields. (C) 2019 Published by Elsevier B.V.