5-(4-(trifluoromethyl)phenyl)-1H-indole | 163105-69-9

• 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: 5-(4-(trifluoromethyl)phenyl)-1H-indole
• 英文别名: 5-[4-(trifluoromethyl)phenyl]-1H-indole
• CAS: 163105-69-9
• 化学式: C₁₅H₁₀F₃N
• 分子量: 261.246
• InChiKey: NUCXSZRYNNYZIB-UHFFFAOYSA-N

物化性质

• 沸点：
  378.3±37.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：
  15.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-(trifluoromethyl)phenyl)-1H-indole 在 potassium phosphate 、 copper(l) iodide 、 sodium cyanoborohydride 、 对甲苯磺酸 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 3-(3-(5-(4-(trifluoromethyl)phenyl)-1H-indol-1-yl)benzylamino)benzoic acid
  参考文献：
  名称：

  Using ‘biased-privileged’ scaffolds to identify lysine methyltransferase inhibitors

  摘要：

  Methylation of histones by lysine methyltransferases (KMTases) plays important roles in regulating chromatin function. It is also now clear that improper KMTases activity is linked to human diseases, such as cancer. We report an approach that employs drug-like 'privileged' scaffolds biased with motifs present in S-adenosyl methionine, the cofactor used by KMTases, to efficiently generate inhibitors for Set7, a biochemically well-characterized KMTase. Setin-1, the most potent inhibitor of Set7 we have developed also inhibits the KMTase G9a. Together these data suggest that these inhibitors should provide good starting points to generate useful probes for KMTase biology and guide the design of KMTase inhibitors with drug-like properties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.024
• 作为产物：
  描述：

  4-三氟甲基苯磺酰氯 在 potassium phosphate 、 potassium hydrogen difluoride 、 palladium diacetate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 5-(4-(trifluoromethyl)phenyl)-1H-indole
  参考文献：
  名称：

  “唤醒”芳基磺酰氟：铃木-宫浦偶联反应的新伙伴

  摘要：

  使用 Pd(OAc) 2催化的 Suzuki-Miyaura 偶联反应中的新伙伴描述了 -SO 2 F 基团的活化示例，该基团传统上被认为即使在存在过渡金属的情况下也是稳定的基团，并且Ruphos 作为配体。产品在最佳条件下表现出良好至出色的收率和广泛的官能团相容性。非对称三联苯的顺序合成和克级工艺突出了该方法的合成效用。DFT 计算表明 Pd 0更喜欢插入 C-S 键而不是 S-F 键之间。

  DOI：

  10.1039/d1nj05469d

文献信息

• Total synthesis of (±) aspidostomide B, C, regioisomeric N-methyl aspidostomide D and their derivatives
  作者：Mulla Althafh Hussain、Faiz Ahmed Khan

  DOI：10.1016/j.tetlet.2019.151040

  日期：2019.9

  A full account of the total synthesis of aspidostomide B, C, their analogues and our synthetic efforts towards the synthesis of aspidostomide D, which led to the synthesis of regioisomeric N-methyl aspidostomide D, its analogues via epoxide opening strategy is presented. The synthesis of regioisomeric N-methyl aspidostomide D involves an efficient, five-step sequence, with 36.3% overall yield, starting

  全面介绍了杀虫威B，C，其类似物的总合成以及我们为合成杀虫威D而进行的合成努力，该合成导致了通过环氧化物开放策略合成区域异构体N-甲基杀虫威D。从3,4,5-三溴-1H-吡咯-2-羧酸开始，区域异构体N-甲基蛇毒苷D的合成涉及有效的五步序列，总收率达36.3％。该方案的关键特征是分子内环化，脱水，氧化和路易斯酸介导的区域选择性环氧化物环的2,5-二溴-1H-吲哚的C-3位置开环，以提供标题化合物。
• Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C–H Activation
  作者：Yan-Hua Liu、Pei-Pei Xie、Lei Liu、Jun Fan、Zhuo-Zhuo Zhang、Xin Hong、Bing-Feng Shi

  DOI：10.1021/jacs.1c08562

  日期：2021.11.17

  we reported a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by a new type of tailor-made amino acid ligands. Critical to the chiral induction was the engaging of a novel noncovalent interaction (NCI), which has seldomly been disclosed in the C–H activation area, arising from the molecular recognition among the organocobalt(III) intermediate, the coordinated

  未活化末端烯烃的对映选择性加氢芳基化是有机化学中的一个突出挑战。在此，我们报道了一种由新型特制氨基酸配体辅助的 Cp*Co(III) 催化的未活化脂肪族末端烯烃的不对称氢化芳基化。手性诱导的关键是新的非共价相互作用 (NCI) 的参与，这种相互作用在 C-H 活化领域很少被披露，这是由有机钴 (III) 中间体、配位烯烃和孔之间的分子识别引起的。 -设计的手性配体。以高产率和优异的对映选择性获得了范围广泛的 C2-烷基化吲哚。DFT 计算揭示了反应机理并阐明了立体确定烯烃插入步骤中手性诱导的起源。
• INDOLE DERIVATIVES USEFUL AS GLUCAGON RECEPTOR ANTAGONISTS
  申请人：Janssen Pharmaceutica NV

  公开号：US20180064686A1

  公开（公告）日：2018-03-08

  The present invention is directed to indole derivatives, pharmaceutical compositions containing them and their use in the treatment and/or prevention of disorders and conditions ameliorated by antagonizing one or more glucagon receptors, including for example metabolic diseases such as Type II diabetes mellitus and obesity.

  本发明涉及吲哚衍生物、含有它们的药物组合物以及它们在治疗和/或预防通过拮抗一个或多个胰高血糖素受体而改善的疾病和症状的用途，包括例如代谢疾病，如2型糖尿病和肥胖症。
• Concatenating Suzuki Arylation and Buchwald–Hartwig Amination by A Sequentially Pd‐Catalyzed One‐Pot Process—Consecutive Three‐Component Synthesis of <i>C</i> , <i>N</i> ‐Diarylated Heterocycles
  作者：Laura Mayer、Regina Kohlbecher、Thomas J. J. Müller

  DOI：10.1002/chem.202003837

  日期：2020.11.26

  concise, modular and efficient one‐pot approach to diversely functionalized heterocycles, as exemplified for 3,10‐diaryl 10H‐phenothiazines, 3,9‐diaryl 9H‐carbazoles, and 1,5‐diaryl 1H‐indoles, in high yields starting from simple staring materials. Moreover, this one‐pot reaction is a sequentially palladium‐catalyzed process that does not require additional catalyst loading after the first coupling

  连续多组分反应中Suzuki偶联和Buchwald-Hartwig胺的串联反应为各种官能化的杂环打开了一种简洁，模块化且有效的一锅法，例如3,10-二芳基10 H-吩噻嗪，3,9-二芳基9 H-咔唑和1,5-二芳基1 H-吲哚从简单的凝视材料开始就可以高收率。此外，该单釜反应是钯顺序催化的过程，在第一步偶联步骤之后不需要额外的催化剂负载量。
• Synthesis of heterobiaryls via Suzuki-Miyaura coupling reaction of potassium aryltrifluoroborates with heteroaryl halides in aqueous systems
  作者：Leifang Liu、Kai Zhao、Wenbo Li、Mingli Liu、Yuting Chen、Yan Dong

  DOI：10.1002/aoc.4831

  日期：2019.4

  A variety of heterobiaryl compounds have been synthesized by the Suzuki‐Miyaura coupling reactions of heteroaryl halides with potassium aryltrifluoroborates. Pd (OAc)2 was found to be highly efficient for the Suzuki‐Miyaura coupling reactions of various heteroaryl halides with potassium aryltrifluoroborates in aqueous systems, delivering the corresponding heterobiaryl compounds in good to excellent

  杂芳基卤化物与芳基三氟硼酸钾的Suzuki-Miyaura偶联反应合成了各种杂二芳基化合物。发现Pd（OAc）2对于水性系统中各种杂芳基卤化物与芳基三氟硼酸钾的Suzuki-Miyaura偶联反应非常有效，可提供相应的杂二芳基化合物，收率非常好。