N-(3-trifluoromethylphenyl)indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(3-trifluoromethylphenyl)indole
• 英文别名: 1-[3-(Trifluoromethyl)phenyl]-1H-indole；1-[3-(trifluoromethyl)phenyl]indole
• 化学式: C₁₅H₁₀F₃N
• 分子量: 261.246
• InChiKey: AWYGNUKKUOCHRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 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：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-trifluoromethylphenyl)indole 在 sodium hypochlorite 、 lithium hydroxide monohydrate 、 盐酸羟胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 水 为溶剂， 反应 37.25h， 生成 5-methyl-3-(1-(3-(trifluoromethyl)phenyl)-1H-indol-3-yl)-4,5-dihydroisoxazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of novel MIF antagonists

  摘要：

  Two series of novel furan and indole compounds were synthesized and probed for inhibition of macrophage migration inhibitory factor (MIF) activity. Several compounds from both series inhibited the enzymatic activity of MIF at levels equal to or significantly better than ISO-1 (an early MIF inhibitor). The majority of the compounds that robustly inhibited the spontaneous secretion/release/recognition of MIF from freshly isolated human peripheral blood mononuclear cells were from the furan series (compounds 5, 9, 13, 15, and 16). In contrast, compounds that markedly inhibited the MIF-induced production of pro-inflammatory cytokines were predominantly from the indole series (compounds 26, 29, and 32). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.127
• 作为产物：
  描述：

  3-氯苯乙烯 在 palladium on activated charcoal potassium tert-butylate 、 ammonium formate 作用下， 以 甲苯 为溶剂， 反应 41.0h， 生成 N-(3-trifluoromethylphenyl)indole
  参考文献：
  名称：

  无芳基氯化物的无过渡金属胺化反应合成2,3-二氢吲哚，吲哚和苯胺。

  摘要：

  脂族和芳族胺在叔丁醇钾的存在下与2-和3-氯苯乙烯反应，以高收率得到N-取代的2,3-二氢吲哚。这种多米诺胺化方案与合适的脱氢反应的结合，使一锅操作即可获得药理学上有趣的吲哚。通过这种方法，从市售底物开始获得＞ 50％的N-取代的吲哚的总产物产率。除了芳族C-Cl键的分子内碱促进的胺化以外，还描述了芳族氯化物与伯胺和仲胺的无金属分子间胺化。使用叔丁醇钾作为碱可合成各种苯胺，收率良好至极佳。由于形成芳烃中间体，

  DOI：

  10.1021/jo001544m

文献信息

• [EN] TARGETED BIFUNCTIONAL DEGRADERS<br/>[FR] AGENTS DE DÉGRADATION BIFONCTIONNELS CIBLÉS
  申请人：UNIV YALE

  公开号：WO2021072269A1

  公开（公告）日：2021-04-15

  The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.

  本发明在一个方面提供了可以用来促进或增强降解某些循环蛋白的双功能化合物。在另一个方面，本发明提供了可以用来促进或增强降解某些自身抗体的双功能化合物。在某些实施方式中，治疗或管理疾病和/或疾病需要降解、去除或减少受试者体内循环蛋白或自身抗体的浓度。因此，在某些实施方式中，将本发明的化合物给予受试者可去除或减少循环蛋白或自身抗体的循环浓度，从而治疗、改善或预防疾病和/或疾病。在某些实施方式中，循环蛋白是TNF。
• An efficient synthesis of N-substituted indoles from indoline/indoline carboxylic acid via aromatization followed by C–N cross-coupling reaction by using nano copper oxide as a recyclable catalyst
  作者：K. Harsha Vardhan Reddy、G. Satish、K. Ramesh、K. Karnakar、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2012.04.012

  日期：2012.6

  new and elegant protocol for the synthesis of 1-substituted indoles was developed via aromatization of indoline/indoline carboxylic acid followed by C–N cross-coupling with various aryl halides in the presence of nano CuO as a recyclable catalyst, Cs2CO3 as a base in DMSO at 80 °C. 1-Substituted indoles were obtained in good to excellent yields and the catalytic system can be recycled up to four cycles

  通过将二氢吲哚/二氢吲哚羧酸芳构化，然后在作为可回收催化剂的纳米CuO Cs 2 CO 3的存在下，与各种芳基卤化物进行C–N交叉偶联，开发了一种新的且优雅的合成1-取代的吲哚的方案。在80°C下用作DMSO的碱。得到的1-取代的吲哚的收率高至优异，催化体系最多可循环使用四个循环而不会损失催化活性。
• Synthesis of <i>gem</i> ‐Difluoro Olefins through C−H Functionalization and β‐fluoride Elimination Reactions
  作者：Zhen Yang、Mieke Möller、Rene M. Koenigs

  DOI：10.1002/anie.201915500

  日期：2020.3.27

  reported. This approach provides for the first time a facile method for the rapid synthesis of gem-difluoro olefins using fluorinated diazoalkanes under mild reaction conditions. Cyclopropanation products were obtained when N-arylated rather than N-alkylated indoles were applied in this reaction. Mechanistic studies reveal the importance of the β-fluoride elimination step in this transformation. This method

  报道了钯催化的CH官能化和吲哚杂环与氟化的重氮烷烃之间连续的β-氟化物消除反应。该方法首次为在温和的反应条件下使用氟化的重氮烷烃快速合成宝石二氟烯烃提供了一种简便的方法。当在该反应中使用N-芳基化而不是N-烷基化的吲哚时，获得了环丙烷化产物。机理研究表明，在这种转化过程中，β-氟化物消除步骤的重要性。该方法为1-芳基-（2,2-二氟乙烯基）基团的简单直接转移提供了新的概念，从而获得了宝石-二氟烯烃。
• A ligand-free copper(I) oxide catalyzed strategy for the N-arylation of azoles in water
  作者：Fui-Fong Yong、Yong-Chua Teo、Siew-Hoon Tay、Bryan Yong-Hao Tan、Kim-Huat Lim

  DOI：10.1016/j.tetlet.2011.01.005

  日期：2011.3

  A simple and practical protocol has been developed for the cross-coupling of azoles and aryl iodides under ligand-free copper(I) oxide catalyzed conditions in water. The protocol uses tetrabutylammonium bromide (TBAB) as the phase-transfer catalyst, and water as the solvent, and shows good tolerance towards various functional groups.

  已经开发了一种简单而实用的方案，用于在水中的无配体氧化铜（I）催化条件下将唑类与芳基碘化物进行交叉偶联。该方案使用四丁基溴化铵（TBAB）作为相转移催化剂，并使用水作为溶剂，并且对各种官能团均显示出良好的耐受性。
• Synthesis of Chiral <i>cis</i>-Cyclopropane Bearing Indole and Chromone as Potential TNFα Inhibitors
  作者：Ryutaro Kanada、Makoto Tanabe、Ryuta Muromoto、Yukina Sato、Tomoki Kuwahara、Hayato Fukuda、Mitsuhiro Arisawa、Tadashi Matsuda、Mizuki Watanabe、Satoshi Shuto

  DOI：10.1021/acs.joc.8b00466

  日期：2018.8.3

  Conformationally restricted analogues of SPD-304, the first small-molecule TNFα inhibitor, in which two heteroaryl groups, indole and chromone, are connected by chiral methyl- or ethyl-cis-cyclopropane, were designed. Synthesis of these molecules was achieved via Suzuki–Miyaura or Stille coupling reactions with chiral bromomethylenecyclopropane or iodovinyl-cis-cyclopropane as the substrate, both of

  设计了第一个小分子TNFα抑制剂SPD-304的构象受限类似物，其中两个杂芳基（吲哚和色酮）通过手性甲基或乙基-顺式-环丙烷连接。这些分子的合成是通过以手性溴亚甲基环丙烷或碘乙烯基-顺-环丙烷为底物的Suzuki-Miyaura或Stille偶联反应实现的，两者均由手性亚甲基环丙烷作为常见中间体制备，构建了杂芳基-甲基或-乙基-顺式-环丙烷结构是关键步骤。这项研究提出了具有两个杂芳基的一系列手性顺式-环丙烷共轭物的有效合成。