2-(4-fluorophenyl)-3-methyl-1-phenyl-1H-indole

• 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: 2-(4-fluorophenyl)-3-methyl-1-phenyl-1H-indole
• 英文别名: 2-(4-Fluorophenyl)-3-methyl-1-phenylindole
• 化学式: C₂₁H₁₆FN
• 分子量: 301.363
• InChiKey: WOQDCILAHZHGEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  邻硝基苯乙酮 在 氢氧化钾 、 氧气 2-双环己基膦-2',6'-二甲氧基联苯 、 2,6-二甲基吡啶 、 palladium diacetate 、 potassium phosphate 、 copper diacetate 、 potassium tert-butylate 、 肉豆蔻酸 、 三苯基膦 、 tin(ll) chloride 作用下， 以 乙醇 、 正庚烷 、 甲苯 、 苯 为溶剂， 反应 17.5h， 生成 2-(4-fluorophenyl)-3-methyl-1-phenyl-1H-indole
  参考文献：
  名称：

  Pd-Catalyzed Tandem C−N/C−C Coupling of gem-Dihalovinyl Systems:  A Modular Synthesis of 2-Substituted Indoles

  摘要：

  2-Substituted indoles were synthesized via a Pd-catalyzed tandem C-N/Suzuki-Miyaura coupling from readily prepared ortho-gemdihalovinylanilines. Optimal conditions used a Pd(OAC)(2)/S-Phos catalyst in the presence of (K3PO4H2O)-H-. and an organoboron reagent, which included boronic acids, esters, alkyl 9-BBN derivatives, and trialkylboranes. Yields of the desired indoles were good to excellent using low catalyst loadings (typically 1 mol %).

  DOI：

  10.1021/ol051286l

文献信息

• A Highly Selective Tandem Cross-Coupling of <i>gem</i>-Dihaloolefins for a Modular, Efficient Synthesis of Highly Functionalized Indoles
  作者：Yuan-Qing Fang、Mark Lautens

  DOI：10.1021/jo701987r

  日期：2008.1.1

  A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline

  使用吲哚合成法的高效率的方法偕- dihalovinylaniline底物和有机硼试剂经由Pd催化的分子内串联胺化和分子间Suzuki偶联显影。芳基，烯基和烷基硼试剂均已成功使用，从而形成了一种通用的模块化方法。该反应耐受苯胺上的多种取代方式，从而导致吲哚类化合物的基团在C 2 -C 7处。铜和钯介导的1,2-二芳基吲哚顺序合成的正交方法开发了多种有机硼试剂的广泛应用。
• Screening Methods
  申请人：Lautens Mark

  公开号：US20080039625A1

  公开（公告）日：2008-02-14

  Disclosed are processes for the preparation of 2-substituted indole compounds wherein the 2-substituent comprises an R 4 group, wherein R 4 is selected from the group consisting of monocyclic aromatic, polycyclic aromatic, monocyclic heteroaromatic, polycyclic heteroaromatic, 1° alkyl, and alkenyl, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents, and wherein R 4 is bonded to the 2-position of the indole ring via a C—C bond; the process comprising reacting an orthogem-dihalovinylaniline compound of the formula (I): wherein Halo comprises Br, Cl, or I; each of the one or more R 1 is independently selected from the group consisting of H, fluoro, lower alkyl, lower alkenyl, lower alkoxy, aryloxy, lower haloalkyl, lower alkenyl, —C(O)O-lower alkyl, monocyclic or polycyclic aryl or heteroaryl moiety, or R 1 is an alkenyl group bonded so to as to form a 4- to 20-membered fused monocycle or polycyclic ring with the indole ring; all of which are optionally substituted with one or more suitable substituents at one or more substitutable positions; R 2 comprises H, alkyl, cycloalkyl, aryl, heteroaryl, aryl-loweralkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; R 3 comprises H, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aryl-(C 1-6 )alkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; with an organoboron reagent selected from the group consisting of a boronic ester of R 4 , a boronic acid of R 4 , a boronic acid anhydride of R 4 , a trialkylborane of R 4 and a 9-BBN derivative of R 4 ; in the presence of a base, a palladium metal pre-catalyst and a ligand under reaction conditions effective to form the 2-substituted indole compound. Also disclosed are processes for the preparation of ortho-gem-dihalovinylaniline compounds. Novel compounds prepared by the processes and novel uses of the compounds are likewise disclosed.

  本发明涉及制备2-取代吲哚化合物的方法，其中2-取代基包括R4基团，其中R4从单环芳香族、多环芳香族、单环杂芳族、多环杂芳族、1°烷基和烯基中选择，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换，并且其中R4通过C-C键与吲哚环的2-位置结合；该方法包括将式（I）的正交二卤代乙烯基苯胺化合物与来自以下组的有机硼试剂反应：其中Halo包括Br、Cl或I；其中一个或多个R1各自独立地选择自H、氟、低烷基、低烯基、低烷氧基、芳氧基、低卤代烷基、低烯基、-C（O）O-低烷基、单环或多环芳基或杂芳基基团，或者R1是一个烯基团，通过与吲哚环形成一个4到20个成员的融合的单环或多环环，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；R2包括H、烷基、环烷基、芳基、杂芳基、芳基-低烷基-或杂芳基-低烷基-，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；R3包括H、烷基、卤代烷基、烯基、炔基、芳基、杂芳基、环烷基、杂环、芳基-(C1-6)烷基-或杂芳基-低烷基-，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；在碱、钯金属预催化剂和配体存在下，以有效的反应条件形成2-取代吲哚化合物。本发明还涉及制备正交二卤代乙烯基苯胺化合物的方法。本发明还涉及通过上述方法制备的新化合物以及化合物的新用途。
• WO2006/47888
  申请人：——

  公开号：——

  公开（公告）日：——
• Palladium-Catalyzed Tandem Alkenyl and Aryl C?N Bond Formation: A Cascade N-Annulation Route to 1-Functionalized Indoles
  作者：Michael C. Willis、Gareth N. Brace、Ian P. Holmes

  DOI：10.1002/anie.200461598

  日期：2005.1.7
• 2-SUBSTITUTED INDOLES, THEIR PRECURSORS AND NOVEL PROCESSES FOR THE PREPARATION THEREOF
  申请人：Lautens, Mark

  公开号：EP1817283A1

  公开（公告）日：2007-08-15