3-(4-(trifluoromethyl)benzyl)-1H-indole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-(trifluoromethyl)benzyl)-1H-indole
• 英文别名: 3-[4-(Trifluoromethyl)benzyl]-1H-indole；3-[[4-(trifluoromethyl)phenyl]methyl]-1H-indole
• 化学式: C₁₆H₁₂F₃N
• 分子量: 275.273
• InChiKey: LCJBHFKYCQEMEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚啉 、 4-(三氟甲基)苄醇 在 chloro[5-methoxy-2-[1-[(4-methoxyphenyl)imino-N]ethyl]phenyl-C][(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]iridium 、 potassium carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 19.0h， 以83%的产率得到3-(4-(trifluoromethyl)benzyl)-1H-indole
  参考文献：
  名称：

  吲哚与醇的发散脱氢偶联

  摘要：

  通过简单地改变基础添加剂的添加时间，已经实现了二氢吲哚与被铱络合物催化的醇的脱氢偶联，从而选择性地提供了N-和C3-烷基化的吲哚。iridacycle催化剂在这些反应中起多种作用，使胺和醇都脱氢并催化偶联反应。机理研究表明，借用氢-脱氢过程和脱氢-借入氢过程分别涉及N-烷基化和C3-烷基化反应。C3-烷基化反应涉及两个sp3碳中心的直接偶联。

  DOI：

  10.1021/acscatal.6b03667

文献信息

• Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols
  作者：Anggi Eka Putra、Kei Takigawa、Hatsuki Tanaka、Yoshihiko Ito、Yohei Oe、Tetsuo Ohta

  DOI：10.1002/ejoc.201300744

  日期：2013.10

  Pd/C and RuCl2(PPh3)3/DPEphos effectively catalyzed the alkylation of indole with alcohols to give 3‐substituted indoles selectively. Various types of substrates were examined and were found to give the corresponding 3‐substituted indoles in up to 99 % yield. Under different reaction conditions, RuCl2(PPh3)3/DPEphos catalyzed the selective formation of bis(3‐indolyl)phenylmethane derivatives.

  Pd / C和RuCl 2（PPh 3）3 / DPEphos有效地催化了吲哚与醇的烷基化反应，从而选择性地生成了3个取代的吲哚。检查了各种类型的底物，发现它们以高达99％的产率提供了相应的3-取代的吲哚。在不同的反应条件下，RuCl 2（PPh 3）3 / DPEphos催化了双（3-吲哚基）苯基甲烷衍生物的选择性形成。
• Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen
  作者：Giovanni Di Gregorio、Michele Mari、Francesca Bartoccini、Giovanni Piersanti

  DOI：10.1021/acs.joc.7b01603

  日期：2017.8.18

  We present the coupling of primary and secondary benzyl alcohols with indoles to form 3-benzylated indoles and H2O that is catalyzed, for the first time, by a complex of earth-abundant iron. This transformation accommodates a variety of substrates and is distinguished by its operational simplicity, sustainability, high functional-group tolerance, and amenability to gram-scale synthesis. On the basis

  我们提出伯和仲苄醇与吲哚的偶合，以形成3-苄基化的吲哚和H 2 O，这是第一次由富地球的铁的复合物催化。这种转变可容纳多种底物，并且以其操作简单，可持续性，高官能团耐受性和对克级合成的适应性而著称。根据初步的实验观察，我们建议反应通过借入氢过程进行。
• Rapid and General Protocol towards Catalyst-Free Friedel-Crafts C-Alkylation of Indoles in Water Assisted by Microwave Irradiation
  作者：Margherita De Rosa、Annunziata Soriente

  DOI：10.1002/ejoc.200901333

  日期：2010.2

  uncatalyzed Friedel― Crafts alkylation of indoles using microwave irradiation in water is described. A series of functionalized indole derivatives has been synthesized in very short times with moderate to good yields. The combination of microwave irradiation and superheated water offers significant advantages over conventional methods, such as higher selectivities, simplicity, shorter reaction times, and

  描述了一种使用微波辐射在水中对吲哚进行非催化 Friedel-Crafts 烷基化的有效且简化的方案。一系列功能化的吲哚衍生物已在很短的时间内以中等至良好的产率合成。微波辐射和过热水的结合提供了优于传统方法的显着优势，例如更高的选择性、简单性、更短的反应时间以及不需要催化剂。
• [EN] OXIDIZED BIS(3-INDOLYL)METHANES AND USES THEREOF<br/>[FR] BIS(3-INDOLYL)MÉTHANES OXYDÉS ET UTILISATIONS ASSOCIÉES
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2019183527A1

  公开（公告）日：2019-09-26

  Disclosed herein are compounds capable of inducing apoptosis through promoting Nur77 interaction with Bcl-2 and through modulating mitochondrial activities. Also disclosed herein are compositions and methods using these compounds and compositions. Nur77 is a key regulator of Bcl-2 activities and is capable of converting Bcl-2 from an anti-apoptotic protein to a pro-apoptotic protein. Small molecules that directly modulate the Nur77/Bcl-2 apoptotic pathways are promising for treating diseases with abnormal levels of Bcl-2, Nur77, or combinations thereof, including cancers.

  本文揭示了一些化合物，能够通过促进Nur77与Bcl-2的相互作用以及调节线粒体活性来诱导细胞凋亡。同时，本文还揭示了使用这些化合物和组合物的组成和方法。Nur77是Bcl-2活性的关键调节因子，能够将Bcl-2从抗凋亡蛋白转变为促凋亡蛋白。直接调节Nur77/Bcl-2凋亡途径的小分子对于治疗Bcl-2、Nur77或两者组合异常水平的疾病，包括癌症，是很有前途的。
• Efficient copper-catalyzed synthesis of C3-alkylated indoles from indoles and alcohols
  作者：Ngoc-Khanh Nguyen、Duong Ha Nam、Ban Van Phuc、Van Ha Nguyen、Quang Thang Trịnh、Tran Quang Hung、Tuan Thanh Dang

  DOI：10.1016/j.mcat.2021.111462

  日期：2021.4

  A highly efficient copper(II) catalyst system for alkylation of indoles with alcohols via hydrogen borrowing method has been developed to afford C3-alkylated indoles in good to excellent yields. Cu(OAc)2 in the combination with dppm ligand has been found to be the most suitable catalyst system for this alkylation reaction.

  已经开发了一种通过氢借位方法将吲哚与醇烷基化的高效铜（II）催化剂体系，可以以良好或极好的收率得到C3-烷基化的吲哚。已经发现与dppm配体结合的Cu（OAc）2是最适合该烷基化反应的催化剂体系。