3-bromo-2-(4-methoxyphenyl)benzo[b]thiophene | 26563-22-4

• 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: 3-bromo-2-(4-methoxyphenyl)benzo[b]thiophene
• 英文别名: 3-bromo-2-(4-methoxyphenyl)-1-benzothiophene
• CAS: 26563-22-4
• 化学式: C₁₅H₁₁BrOS
• 分子量: 319.222
• InChiKey: YIWVFVOZIOKSJY-UHFFFAOYSA-N

物化性质

• 熔点：
  84.5-86.5 °C
• 沸点：
  431.8±35.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-2-(4-methoxyphenyl)benzo[b]thiophene 在 正丁基锂 、 三溴化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 25.17h， 生成 1-[2-[4-[[2-[4-(2-Pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-3-yl]sulfanyl]phenoxy]ethyl]pyrrolidine
  参考文献：
  名称：

  Diamino Benzo[b]thiophene Derivatives as a Novel Class of Active Site Directed Thrombin Inhibitors. 5. Potency, Efficacy, and Pharmacokinetic Properties of Modified C-3 Side Chain Derivatives

  摘要：

  A systematic investigation of the structure-activity relationships of the C-3 side chain of the screening hit la led to the identification of the potent thrombin inhibitors 23c, 28c, and 31c. Their activities (1240, 903, and 1271 x 10(6) L/mol, respectively) represent 2200- and 2900-fold increases in potency over the starting lead la. This activity enhancement was accomplished with an increase of thrombin selectivity. The in vitro anticoagulant profiles of derivatives 28c and 31c were determined, and they compare favorably with the clinical agent H-R-1-[4aS,-8aS]perhydroisoquinolyl-prolyl-arginyl aldehyde (D-Piq-Pro-Arg-H; 32). The more potent members of this series have been studied in an arterial/venous shunt (AV shunt) model of thrombosis and were found to be efficacious in reducing clot formation. However, their efficacy is currently limited by their rapid and extensive distribution following administration.

  DOI：

  10.1021/jm9903388
• 作为产物：
  描述：

  (2-((4-methoxyphenyl)ethynyl)phenyl)(methyl)sulfane 在 bis(N-methyl-2-pyrrolidinone)hydrogen tribromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到3-bromo-2-(4-methoxyphenyl)benzo[b]thiophene
  参考文献：
  名称：

  MPHT 促进邻位取代芳炔的溴环化：在合成 2-取代 3-溴苯并呋喃和 -苯并 [b] 噻吩中的应用

  摘要：

  开发了一种合成 2-取代 3-溴苯并呋喃和-苯并噻吩的简便通用方法。该过程基于邻位取代芳炔在 N-甲基吡咯烷-2-酮氢三溴化物 (MPHT) 作为柔软且易于处理的亲电子溴化试剂存在下的环化反应。在温和的反应条件下，MPHT 促进了各种烯炔和二炔以及芳炔的溴环化，以高产率获得 2-取代的 3-溴苯并呋喃和-苯并噻吩。随后在 C-Br 键上通过钯催化的偶联反应进行的功能化提供了获得具有生物学意义的 2,3-二取代苯并呋喃和苯并噻吩的通用途径。

  DOI：

  10.1002/ejoc.201000529

文献信息

• Antithrombotic diamines
  申请人：Eli Lilly and Company

  公开号：US06025382A1

  公开（公告）日：2000-02-15

  This application relates to the use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents of diamines of formula I as defined herein. It also provides novel compounds of formula I, processes and intermediates for their preparation, and pharmaceutical formulations comprising the novel compounds of formula I.

  该应用涉及将I式中所定义的二胺用作凝血酶抑制剂、凝血抑制剂和血栓栓塞性疾病药剂。它还提供了I式的新化合物，其制备方法和中间体，以及包含这些新化合物的药物配方。
• Toward a Greener Barluenga–Valdés Cross-Coupling: Microwave-Promoted C–C Bond Formation with a Pd/PEG/H₂O Recyclable Catalytic System
  作者：Diana Lamaa、Estelle Messe、Vincent Gandon、Mouad Alami、Abdallah Hamze

  DOI：10.1021/acs.orglett.9b03310

  日期：2019.11.1

  for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos–SO3Na or Pd/MeDavephos–CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its

  已开发出一种绿色的Barluenga-Valdés交叉偶联反应，利用钯催化合成1,1-二芳基乙烯。发现在微波辐射下，基于PEG / H 2 O中Pd / Xphos-SO 3 Na或Pd / MeDavephos-CF 3 SO 3的新催化体系是该转化的最佳条件。还对钯催化剂体系的可回收性进行了研究，发现钯催化剂体系在九次运行中均具有活性，而活性没有明显损失。
• Synthesis of a 3-(α-Styryl)benzo[<i>b</i>]-thiophene Library via Bromocyclization of Alkynes and Palladium-Catalyzed Tosylhydrazones Cross-Couplings: Evaluation as Antitubulin Agents
  作者：Bret Tréguier、Marie Lawson、Guillaume Bernadat、Jérôme Bignon、Joëlle Dubois、Jean-Daniel Brion、Mouad Alami、Abdallah Hamze

  DOI：10.1021/co500115b

  日期：2014.12.8

  efficiently synthesized by applying a synthetic sequence that allowed introduction of various substituents on aromatic A, B, and C-rings. The strategy developed involves the synthesis of 3-bromobenzo[b]thiophene derivatives through a bromocyclization step of methylthio-containing alkynes using N-methylpyrrolidin-2-one hydrotribromide reagent (MPHT). Further coupling of 3-bromobenzothiophenes under palladium-catalysis

  通过应用允许在芳族A，B和C-上引入各种取代基的合成序列，有效合成了具有高水平分子多样性的功能化3-（α-苯乙烯基）-苯并[ b ]噻吩文库戒指。所开发的策略涉及通过使用N-甲基吡咯烷基-2-酮氢三溴化试剂（MPHT）通过含甲硫基炔烃的溴环化步骤合成3-溴苯并[ b ]噻吩衍生物。钯催化下的3-溴苯并噻吩与N-甲苯磺酰hydr的进一步偶联有效地提供了2-芳基-3-（α-苯乙烯基）苯并[ b噻吩衍生物。研究了目标化合物的抗增殖特性。其中，化合物5m对HCT-116细胞系表现出亚微摩尔的细胞毒活性，并在微摩尔水平上可与CA-4相比抑制微管蛋白的聚合。
• Synthesis of novel benzo[b]furans and benzo[b]thiophenes: analogs of combretastatin and resveratrol
  作者：Jay Chauhan、Alexandre R. Monteil、Steven E. Patterson

  DOI：10.1515/hc.2010.003

  日期：2010.1.1

  Abstract A rapid and efficient synthesis of fused polyphenolic/polymethoxy benzofurans and benzothiophenes that have potential as antitumor agents and components of anti-HIV combination therapy has been achieved.

  摘要 融合多酚/多甲氧基苯并呋喃和苯并噻吩的快速有效合成已经实现，它们具有作为抗肿瘤药物和抗 HIV 联合治疗成分的潜力。
• Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3, n -dihalobenzo[ b ]thiophenes
  作者：Tanay Kesharwani、Cory Kornman、Amanda Tonnaer、Amanda Hayes、Seoyoung Kim、Nikesh Dahal、Ralf Romero、Andrew Royappa

  DOI：10.1016/j.tet.2018.04.080

  日期：2018.6

  A convenient methodology for the synthesis of mono- and di-halogenated benzo[b]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed method is facile, uses ethanol as a green solvent, and results in uniquely substituted benzo[b]thiophene structures with isolated yields up to 96%. The

  本文描述了合成单和二卤代苯并[b]噻吩的简便方法，该方法在取代的2-炔基硫代苯甲醚存在下利用五水合硫酸铜（II）和各种卤化钠。所提出的方法简便易行，使用乙醇作为绿色溶剂，并能产生独特取代的苯并[b]噻吩结构，分离产率高达96％。该方法最有用的组成部分是在苯并[b]噻吩环周围的每个可用位置（2-7）处选择性引入溴原子，同时使位置3保留在特定的卤素原子（例如Cl，Br或I）上。芳香族卤素是有用的反应性处理剂。因此，在特定位置选择性引入卤素对于通过金属催化的交叉偶联反应有针对性地合成生物活性分子和复杂的有机材料具有重要意义。这项工作是一种合成二卤代苯并[b]噻吩核心结构的新颖方法，为本文讨论的当前方法提供了一种出色的替代方法。