2-methylbenzo[b]thiophen-5-amine | 157589-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-methylbenzo[b]thiophen-5-amine
• 英文别名: 2-Methyl-1-benzothiophen-5-amine
• CAS: 157589-58-7
• 化学式: C₉H₉NS
• 分子量: 163.243
• InChiKey: LNLBCAYNZRIXHG-UHFFFAOYSA-N

物化性质

• 沸点：
  328.5±22.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylbenzo[b]thiophen-5-amine 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 18-冠醚-6 、 铜 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 邻二氯苯 为溶剂， 反应 25.0h， 生成 4-[3,3,4,4,5,5-hexafluoro-2-[2-methyl-5-(N-phenylanilino)-1-benzothiophen-4-yl]cyclopenten-1-yl]-2-methyl-N,N-diphenyl-1-benzothiophen-5-amine
  参考文献：
  名称：

  Synthesis, fine structure of 19F NMR and fluorescence of novel amorphous TPA derivatives having perfluorinated cyclopentenyl and benzo[b]thiophene unit

  摘要：

  Three novel triphenylamine (TPA) derivatives having perfluorinated cyclopentenyl and benzo[b]thiophene unit are obtained from 4-bromo-N,N-diphenyl-2-methylbenzo[b]thiophen-5-amine. The new compounds are expected to find their use in thin film devices as charge transport materials and host organic light-emitting materials. It is found that the new compounds show relatively strong fluorescence either in solution or in solid state, and are amorphous due to a special conformation which is elucidated by the fine structure of F-19 NMR. Molecular structure and properties of these compounds is characterized by H-1 NMR, C-13 NMR (broadband decoupled), ESI-HRMS, elemental analysis and thermal analysis (DSC). Fluorescent quantum yield in solution is measured using 9,10-diphenylanthrancene (DPA) as standard fluorescent substance. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.01.019
• 作为产物：
  描述：

  N-(2-methylbenzo[b]thiophen-5-yl)acetamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2-methylbenzo[b]thiophen-5-amine
  参考文献：
  名称：

  Synthesis, fine structure of 19F NMR and fluorescence of novel amorphous TPA derivatives having perfluorinated cyclopentenyl and benzo[b]thiophene unit

  摘要：

  Three novel triphenylamine (TPA) derivatives having perfluorinated cyclopentenyl and benzo[b]thiophene unit are obtained from 4-bromo-N,N-diphenyl-2-methylbenzo[b]thiophen-5-amine. The new compounds are expected to find their use in thin film devices as charge transport materials and host organic light-emitting materials. It is found that the new compounds show relatively strong fluorescence either in solution or in solid state, and are amorphous due to a special conformation which is elucidated by the fine structure of F-19 NMR. Molecular structure and properties of these compounds is characterized by H-1 NMR, C-13 NMR (broadband decoupled), ESI-HRMS, elemental analysis and thermal analysis (DSC). Fluorescent quantum yield in solution is measured using 9,10-diphenylanthrancene (DPA) as standard fluorescent substance. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.01.019

文献信息

• Cyanoguanidine-based lactam derivatives as a novel class of orally bioavailable factor Xa inhibitors
  作者：Yan Shi、Jing Zhang、Mengxiao Shi、Stephen P. O’Connor、Sharon N. Bisaha、Chi Li、Doree Sitkoff、Andrew T. Pudzianowski、Saeho Chong、Herbert E. Klei、Kevin Kish、Joseph Yanchunas、Eddie C.-K. Liu、Karen S. Hartl、Steve M. Seiler、Thomas E. Steinbacher、William A. Schumacher、Karnail S. Atwal、Philip D. Stein

  DOI：10.1016/j.bmcl.2009.06.014

  日期：2009.8

  of the thiourea and ketene aminal functional groups. We report the design and synthesis of a novel class of cyanoguanidine-based lactam derivatives as potent and orally active FXa inhibitors. The SAR studies led to the discovery of compound 4 (BMS-269223, Ki = 6.5 nM, EC2xPT = 32 μM) as a selective, orally bioavailable FXa inhibitor with an excellent in vitro liability profile, favorable pharmacokinetics

  的Ñ，Ñ '二取代的氰基胍是在硫脲和乙烯酮缩醛胺官能团的生物电子等排优良。我们报告了新型的氰基胍基内酰胺衍生物作为有效和口服活性FXa抑制剂的设计和合成。SAR研究导致发现化合物4（BMS-269223，K i  = 6.5 nM，EC 2xPT  = 32μM）作为一种选择性的，口服可生物利用的FXa抑制剂，在动物模型中具有出色的体外反应性，良好的药代动力学和药效学。介绍了FXa中4结合的X射线晶体结构，并讨论了关键的配体-蛋白质相互作用。
• “Abnormal” bromination reaction selectivity of 5-diarylamino-2-methylbenzo[b]thiophene caused by a “non-planar” conjugated model: Synthesis and theoretical calculation
  作者：Bian-Peng Wu、Mei-Li Pang、Ting-Feng Tan、Ji-Ben Meng

  DOI：10.1016/j.molstruc.2012.07.054

  日期：2013.1

  5-Diarylamino-2-methylbenzo[b]thiophene was a new kind of triphenylamine-based charge-transporting material. For further modification of the compounds, bromination selectivity was studied through experiments and molecular simulation using Gaussian 09 program under B3LYP/6-311G (d, p) aided by Gaussian View 05 and Multiwfn Program. The results showed that bromination of 5-diarylamino-2-methyl-benzo[b]thiophene

  摘要 5-二芳基氨基-2-甲基苯并[b]噻吩是一种新型的三苯胺基电荷传输材料。为了进一步修饰化合物，在 Gaussian View 05 和 Multiwfn Program 的辅助下，使用 Gaussian 09 程序在 B3LYP/6-311G (d, p) 下通过实验和分子模拟研究了溴化选择性。结果表明，5-二芳基氨基-2-甲基-苯并[b]噻吩的溴化反应发生在“异常”位置（4-和/或4'-位）而不是“正常”位置（3-位） )，这与文献报道的具有简单5-取代基的苯并[b]噻吩衍生物不同。“异常”选择性是由特殊的电子结构引起的，其中存在“类指状”前沿轨道或特殊的“非平面”共轭模型。通过这种电子离域方式，电子会被提供给相连的芳环的邻位和对位，使得TPA单元而不是噻吩环成为选择性的主要因素，4位反应活性能最低。结果通过三种 4-Br 和/或 4'-Br 衍生物化合物 4、5 和 6 的合成得到证实。化合物
• INTERMEDIATES FOR PREPARING INHIBITORS OF HEPATITIS C VIRUS
  申请人：Gilead Sciences, Inc.

  公开号：EP3492464A1

  公开（公告）日：2019-06-05

  Intermediates, used for preparing inhibitors of the hepatitis C virus, of the following formulae are disclosed

  公开了用于制备丙型肝炎病毒抑制剂的下列配方的中间体
• Organic semiconductor element, manufacturing method thereof, composition for forming organic semiconductor film, and method of manufacturing organic semiconductor film
  申请人：FUJIFILM CORPORATION

  公开号：US10651400B2

  公开（公告）日：2020-05-12

  Objects of the present invention is to provide an organic semiconductor element having high mobility and to provide a composition for forming an organic semiconductor film with which an organic semiconductor film having high mobility can be formed, a method of manufacturing an organic semiconductor element formed from the composition for forming an organic semiconductor film, and a method of manufacturing an organic semiconductor film. The organic semiconductor element according to the present invention has a semiconductor active layer including a compound that is represented by Formula 1 and has a molecular weight of 3,000 or less. The composition for forming an organic semiconductor film according to the present invention contains a compound that is represented by Formula 1 and has a molecular weight of 3,000 or less, and a solvent.

  本发明的目的是提供一种具有高迁移率的有机半导体元件，并提供一种用于形成有机半导体薄膜的组合物，用该组合物可以形成具有高迁移率的有机半导体薄膜，还提供一种制造由用于形成有机半导体薄膜的组合物形成的有机半导体元件的方法，以及一种制造有机半导体薄膜的方法。 根据本发明的有机半导体元件具有半导体活性层，其中包括由式 1 表示且分子量在 3,000 或以下的化合物。根据本发明，用于形成有机半导体薄膜的组合物包含一种由式 1 表示且分子量在 3,000 或以下的化合物和一种溶剂。
• MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES
  申请人：Gilead Sciences, Inc.

  公开号：EP2861601B1

  公开（公告）日：2018-02-07