1-(4-氟苯基)-3-甲基-1H-吲哚 | 1011484-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(4-氟苯基)-3-甲基-1H-吲哚
• 英文名称: 1-(4-fluorophenyl)-3-methyl-1H-indole
• 英文别名: 1-(4-Fluorophenyl)-3-methylindole；1-(4-fluorophenyl)-3-methylindole
• CAS: 1011484-24-4
• 化学式: C₁₅H₁₂FN
• 分子量: 225.265
• InChiKey: IXHIHWGRJKRIIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  N-(4-fluorophenyl)-2-(prop-1-en-2-yl)aniline 在 copper(II) 2-ethylhexanoate 、 2,2,6,6-四甲基哌啶氧化物 、 氧气 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以81%的产率得到1-(4-氟苯基)-3-甲基-1H-吲哚
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinyl­anilines with O2 as Terminal Oxidant and TEMPO as Cocatalyst

  摘要：

  A copper-catalyzed intramolecular alkene oxidative amination that utilizes TEMPO as co-catalyst and O₂ as the terminal oxidant has been developed. The method furnishes N-aryl and N-sulfonyl indoles from N-aryl and N-sulfonyl 2-vinylanilines, respectively. Additionally, sequential copper-catalyzed reactions where initial Chan-Lam coupling of 2-vinylanilines with arylboronic acids is followed by oxidative amination of the alkene can generate N-aryl indoles in one pot.

  DOI：

  10.1055/s-0034-1379015

文献信息

• [EN] PYRROLE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRROLE
  申请人：HUA MEDICINE (SHANGHAI) LTD

  公开号：WO2017173604A1

  公开（公告）日：2017-10-12

  Provided herein are compounds of the formula (I) : as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment or prevention of mGluR5 mediated disorders, such as acute and/or chronic neurological disorders, cognitive disorders and memory deficits, as well as acute and chronic pain.

  本文提供了以下式(I)的化合物：以及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及含有它们的药物组合物对于治疗或预防mGluR5介导的疾病，如急性和/或慢性神经系统疾病、认知障碍和记忆缺陷，以及急性和慢性疼痛是有用的。
• Nickel-Catalyzed Mizoroki–Heck/Amination Cascade Reactions of <i>o</i>-Dihaloarenes with Allylamines: Synthesis of Indoles
  作者：Xu Chen、Jin Lin、Biao Wang、Xu Tian

  DOI：10.1021/acs.orglett.0c02909

  日期：2020.10.2

  An efficient Mizoroki–Heck/amination cascade reaction of o-dihaloarenes with allylamines has been developed using nickel and IPr carbene ligand as catalyst. This protocol enables the synthesis of a broad range of substituted indoles by a cascade process, from readily available starting materials. Mechanistic studies suggest that the Mizoroki–Heck reaction occurred first under IPr-nickel catalysis.

  使用镍和IPr卡宾配体作为催化剂，开发了邻二卤代芳烃与烯丙胺的有效Mizoroki-Heck /胺化级联反应。该方案能够通过级联方法从容易获得的起始原料合成各种取代的吲哚。机理研究表明，Mzoroki-Heck反应首先在IPr-镍催化下发生。
• The Catalytic Synthesis of <i>N</i>-Aryl Indoles Featuring an Alternative Disconnection. Hydroaminoalkylation for a Telescoped Reaction Sequence
  作者：Cameron H. M. Zheng、Daria A. Balatsky、Rebecca C. DiPucchio、Laurel L. Schafer

  DOI：10.1021/acs.orglett.2c02510

  日期：2022.9.16

  telescoped synthesis toward C3-methyl-N-aryl indoline and indole products is reported. An in situ generated tantalum(V) ureate catalyst is used for the hydroaminoalkylation of o-chlorostyrene with N-methylaniline to first make a Csp3─Csp3 bond. Subsequent nickel-catalyzed C–N coupling forms N-aryl indolines, and if desired, subsequent oxidation to N-aryl indoles can be achieved using catalytic [Cu(MeCN)4]BF4

  报道了对 C3-甲基-N-芳基二氢吲哚和吲哚产物的三催化伸缩合成。原位生成的脲酸钽(V)催化剂用于邻氯苯乙烯与N-甲基苯胺的氢氨基烷基化反应，首先形成C sp 3 ─C sp 3键。随后的镍催化 C-N 偶联形成N-芳基二氢吲哚，如果需要，随后可以使用催化 [Cu(MeCN) 4 ]BF 4和叔氧化成N-芳基吲哚-丁基过氧-2-乙基己基碳酸酯作为末端氧化剂。该策略突出了用于合成吲哚的替代 C-C 键断开，这是通过原子经济的氢化氨基烷基化反应实现的。使用三步两锅法简化该方法，以提供高达 73% 的各种取代的 C3-甲基-N-芳基吲哚的总分离产率。
• A General Protocol toward Synthesis of 3-Methylindoles Using Acenaphthoimidazolyidene-Ligated Oxazoline Palladacycle
  作者：Ruoqian Fan、Haili Wen、Zhen Chen、Yuanzhi Xia、Weiwei Fang

  DOI：10.1021/acs.orglett.3c03438

  日期：2024.1.12

  An efficient catalytic strategy toward the synthesis of N-substituted 3-methylindoles from inactive o-dihaloarenes and N-allylamines was developed by using a 1,3-bis(2,6-diisopropylphenyl)acenaphthoimidazol-2-ylidene (AnIPr)-ligated oxazoline palladacycle. It enabled a very broad substrate scope tolerating different functional groups, electronic properties, and steric bulkiness and afforded desired

  通过使用 1,3-双(2,6-二异丙基苯基)苊并咪唑-2-亚基 (AnIPr) 连接，开发了一种从无活性的邻二卤代芳烃和N-烯丙胺合成N-取代的 3-甲基吲哚的有效催化策略恶唑啉环钯。它实现了非常广泛的底物范围，可以耐受不同的官能团、电子特性和空间体积，并以良好到优异的产率提供所需的产品。重要的是，它显示出高产率合成多种生物活性化合物和天然产物关键中间体的巨大潜力。
• Palladium-Catalyzed Aryl Amination–Heck Cyclization Cascade: A One-Flask Approach to 3-Substituted Indoles
  作者：Thomas Jensen、Henrik Pedersen、Benny Bang-Andersen、Robert Madsen、Morten Jørgensen

  DOI：10.1002/anie.200703763

  日期：2008.1.18