(3-hydroxybenzo[b]thiophen-2-yl)(thiophen-2-yl)methanone

• 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-hydroxybenzo[b]thiophen-2-yl)(thiophen-2-yl)methanone
• 英文别名: 2-Thenoylbenzo[b]thiophene-3-ol；(3-hydroxy-1-benzothiophen-2-yl)-thiophen-2-ylmethanone
• 化学式: C₁₃H₈O₂S₂
• 分子量: 260.337
• InChiKey: KWKVDQUKABJAPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 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：
  93.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二乙基苯甲酰胺 在 四甲基乙二胺 、 仲丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3-hydroxybenzo[b]thiophen-2-yl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones

  摘要：

  Chemoselective synthesis of thioaurones or 3-hydroxy benzo[b]thiophen-2-aryl ketones, 1-hydroxy naphtho[2,1-b]thiophen-2aryl ketones and chalcones from N,N-diethyl-ortho-methyl sulfanyl aryl amides were described. (Benzo[b]thiophen-2-yl) alkylates and (naphtho[2, 1-b]thiophen-2-yl) alkylates undergo a novel anionic ortho-Fries rearrangement leading to (3-hydroxy benzo[b]thiophen-2-yl) and (1-hydroxy naphtho[2, 1 -b]thiophen-2-yl) alkyl ketones. The hydroxy ketones were used as intermediates in the synthesis of wide range of benzothienopyranones and thiafluorenones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.050

文献信息

• Tricyclic pyrazole derivatives
  申请人：BASF Aktiengesellschaft

  公开号：US06462036B1

  公开（公告）日：2002-10-08

  This invention relates to certain 3-aryl or 3-heteroaryl pyrazoles with 4,5(3,4)-bicyclic ring fusion which are inhibitors of protein kinase activity, of which some are novel compounds, to pharmaceutical compositions containing these pyrazoles and to processes for preparing these pyrazoles.

  这项发明涉及具有4,5(3,4)-双环融合的3-芳基或3-杂芳基吡唑，这些化合物是蛋白激酶活性抑制剂，其中一些是新颖化合物，涉及含有这些吡唑的药物组合物以及制备这些吡唑的方法。
• Facile Synthesis of 2-Substituted Benzo[b]thiophen-3-ols in Water
  作者：Ben Pan、Peng Ren、Haibin Song、Zhihong Wang

  DOI：10.1080/00397911.2011.633203

  日期：2013.5.15

  Abstract A facile synthesis of 2-substituted benzo[b]thiophen-3-ols in a simple reaction system is reported with water as the only media. Density functional theory (DFT) investigations suggest two pathways comparable in energetics: A neutral pathway with concerted C-C bond formation and hydrogen transfer and an anionic pathway with anion attack to the carbonyl group. Studies indicate that water plays

  摘要 据报道，在一个简单的反应体系中，以水为唯一介质，可以轻松合成 2-取代的苯并 [b] 噻吩-3-醇。密度泛函理论 (DFT) 研究表明，在能量学中存在两种可比的途径：具有协调一致的 CC 键形成和氢转移的中性途径和具有对羰基的阴离子攻击的阴离子途径。研究表明，水在这两种情况下都起着至关重要的机械作用。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Iron-Ligand Coordination in Tandem Radical Cyclizations: Synthesis of Benzo[b]thiophenes by a One-pot Reaction of Iron 1,3-Diketone Complexes with 2-Thiosalicylic Acids
  作者：Sharon Lai-Fung Chan、Kam-Hung Low、Chen Yang、Samantha Hui-Fung Cheung、Chi-Ming Che

  DOI：10.1002/chem.201100377

  日期：2011.4.18

  Iron—the mediator: 1,3‐Diketone ligands coordinated to iron undergo unprecedented tandem reactions with 2‐thiosalicylic acids to give 2‐substituted 3‐hydroxylbenzo[b]thiophenes in up to 98 % yield. A similar reaction with 2‐mercaptonicotinic acid gave a thieno[2,3‐b]pyridine derivative in 72 % yield (see scheme). A mechanism involving redox transformation and tandem radical cyclization of the coordinated

  铁—介体：与铁配位的1,3-二酮配体与2-硫代水杨酸进行空前的串联反应，生成2-取代的3-羟基苯并[ b ]噻吩，收率高达98％。与2-巯基烟碱酸的类似反应得到噻吩并[2,3- b ]吡啶衍生物，产率为72％（参见方案）。提出了涉及配体的氧化还原转化和串联自由基环化的机理。
• Application of directed metalation in synthesis. Part 7: Synthesis of suitably functionalised benzo[b]thiophenes as key intermediates in the synthesis of benzothienopyranones
  作者：Tarun Kanti Pradhan、Asish De

  DOI：10.1016/j.tetlet.2005.01.038

  日期：2005.2

  1-(3-hydroxybenzo[b]thiophen-2-yl)ethanone and 1-(3-hydroxybenzo[b]thiophen-2-yl)propan-1-one via an anionic ortho-Fries rearrangement are described. The hydroxy ketones were used as key intermediates in the synthesis of benzothienopyranones.

  一锅合成由邻甲基硫烷基芳基N，N-二乙基酰胺与1-（3-羟基苯并[ b ]噻吩-2-基）乙酮和1合成（3-羟基苯并[ b ]噻吩-2-基）芳基甲酮描述了经由阴离子邻-Fries重排的-（3-羟基苯并[ b ]噻吩-2-基）丙-1-酮。羟基酮用作苯并噻吩并吡喃酮合成中的关键中间体。
• Facile synthesis of substituted 2-aroylbenzo[b]thiophen-3-ols to form novel triazole hybrids using click chemistry
  作者：Asma Mukhtar、Arif Hussain、Faiza Younas、Sammer Yousuf、Muhammad Saeed

  DOI：10.1039/d4ra01146e

  日期：——

  2-aroylbenzo[b]thiophen-3-ol in high yield. To investigate the utility of the synthesized benzothiophene scaffold, an alkyne moiety was introduced at the 3-hydroxy position and subsequently subjected to a click reaction to form novel benzothiophene-triazole hybrids in good yields. A simple and straightforward approach to synthesizing 2-aroylbenzo[b]thiophen-3-ols can open new avenues for discovering novel

  提出了一种在三乙胺存在下，由 2-巯基苯甲酸和各种取代芳基溴甲基酮合成 2-芳酰基苯并[ b ]噻吩-3-醇的有效一锅法。该反应可能是通过在碱存在下，硫代水杨酸中的巯基对溴甲基酮进行 S N 2 型亲核攻击来进行，得到硫烷基苯甲酸，其在原位进行分子内环化，得到 2-芳酰基苯并[ b ]噻吩-3-醇的产率很高。为了研究合成的苯并噻吩支架的实用性，在3-羟基位置引入炔部分，然后进行点击反应，以良好的产率形成新型苯并噻吩-三唑杂化物。一种简单直接的合成 2-芳酰基苯并[ b ]噻吩-3-醇的方法可以为发现新型生物和药物化合物开辟新途径。