N-benzo[b]thien-3-yl-N-(3-pyridyl)amine | 1073552-84-7

• 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: N-benzo[b]thien-3-yl-N-(3-pyridyl)amine
• 英文别名: N-(pyridin-3-yl)benzo[b]thiophen-3-amine；N-(benzo[b]thien-3-yl)pyridin-3-amine；N-(benzothiophen-3-yl)pyridin-3-amine；N-(1-benzothiophen-3-yl)pyridin-3-amine
• CAS: 1073552-84-7
• 化学式: C₁₃H₁₀N₂S
• 分子量: 226.302
• InChiKey: LCTVADJHTMOQRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基吡啶 、 3-溴苯并噻吩 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以48%的产率得到N-benzo[b]thien-3-yl-N-(3-pyridyl)amine
  参考文献：
  名称：

  钯催化的多米诺Ç ？H / N ？H功能化：氮桥杂蒽的有效方法

  摘要：

  钯催化的多米诺Ç  H /Ñ  ħ官能新型含氮桥连thienoacenes的合成和10 ħ -苯并[4,5]噻吩并[3,2- b ]报道从二卤代芳烃吲哚衍生物。该多米诺序列由苯并[ b ]噻吩部分的初始CH功能化，然后是布赫瓦尔德-哈特维格偶联。这种转变对于合成高度π扩展的化合物也很有用。

  DOI：

  10.1002/chem.201500897

文献信息

• A Heteroarylamine Library: Indium-Catalyzed Nucleophilic Aromatic Substitution of Alkoxyheteroarenes with Amines
  作者：Kyohei Yonekura、Yasuhiro Yoshimura、Mizuri Akehi、Teruhisa Tsuchimoto

  DOI：10.1002/adsc.201701452

  日期：2018.3.20

  five‐membered heteroaryl electrophiles fused with/without a benzene ring were found to couple with amines to produce heteroarylamines with broad structural diversity. The heteroarylamine formation proceeds through the cleavage of a heteroaryl−OMe bond by the nucleophilic attack of the amine based on the nucleophilic aromatic substitution (SNAr) reaction. In contrast to the corresponding traditional SNAr amination

  在铟路易斯酸催化下，与/不与苯环稠合的富电子五元杂芳基亲电试剂与胺偶合生成具有广泛结构多样性的杂芳基胺。通过基于亲核芳香取代（S胺的亲核攻击，通过杂芳基- OME键的裂解的杂芳基形成前进Ñ AR）反应。与相应的传统S N Ar胺形成对比，目前基于S N Ar的杂芳基胺化反应无需依赖具有吸电子基团的杂芳基亲电子试剂和亲核性增强的金属酰胺。对NO 2，Br，I，CF 3等官能团的高度相容性观察到CN，CO 2 Et，吡啶基，噻唑基，C = C和OH基团，从而表明该方法的实用性和可靠性。机理研究表明，在此过程中，杂芳基环上可能会形成碳-铟键。
• Antifungal activity of synthetic di(hetero)arylamines based on the benzo[b]thiophene moiety
  作者：Eugénia Pinto、Maria-João R.P. Queiroz、Luís A. Vale-Silva、João F. Oliveira、Agathe Begouin、Jeanne-Marie Begouin、Gilbert Kirsch

  DOI：10.1016/j.bmc.2008.07.042

  日期：2008.9

  The antifungal activity of several di(hetero)arylamine derivatives of the benzo[b]thiophene system was evaluated against clinically relevant Candida, Aspergillus, and dermatophyte species by a broth macrodilution test based on CLSI ( formerly NCCLS) guidelines. The most active compound showed a broad spectrum of activity ( against all tested fungal strains, including fluconazole-resistant fungi), with particularly low MICs for dermatophytes. Results from the inhibition of the dimorphic transition in Candida albicans and flow cytometry studies further confirmed their biological activity. With this study it was possible to establish some structure-activity relationships (SARs). The hydroxy groups proved to be essential for the activity in the aryl derivatives. Furthermore, the spectrum of activity in the pyridine derivatives was broadened by the absence of the ester group on position 2 of the benzo[b]thiophene system. (C) 2008 Elsevier Ltd. All rights reserved.