3-(4-fluorophenyl)benzofuran | 248256-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(4-fluorophenyl)benzofuran
• 英文别名: 3-(4-Fluorophenyl)-1-benzofuran
• CAS: 248256-10-2
• 化学式: C₁₄H₉FO
• 分子量: 212.223
• InChiKey: PUCMDZHPZCLICJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)benzofuran 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 生成 6-(3-[4-fluorophenyl]-benzofuran-2-sulfonyl)-2H-pyridazin-3-one
  参考文献：
  名称：

  A Novel Series of Non-Carboxylic Acid, Non-Hydantoin Inhibitors of Aldose Reductase with Potent Oral Activity in Diabetic Rat Models:  6-(5-Chloro-3-methylbenzofuran-2-sulfonyl)-2H-pyridazin-3-one and Congeners

  摘要：

  Discovery of a highly selective, potent, and safe non-carboxylic acid, non-hydantoin inhibitor of aldose reductase (AR) capable of potently blocking the excess glucose flux through the polyol pathway that prevails under diabetic conditions has been a long-standing challenge. In response, we did high-throughput screening of our internal libraries of compounds and identified 6-phenylsulfonylpyridazin-2H-3-one, 8, which showed modest inhibition of AR, both in vitro and in vivo. Initial structure-activity relationships concentrated on phenyl substituents and led to 6-(2,4-dichlorophenylsulfonyl)-2H-pyridazin-3-one, 81, which was more potent than 8, both in vitro and in vivo. Incorporation of extant literature findings with other aldose reductase inhibitors, including zopolrestat, resulted in the title inhibitor, 19m, which is one of the most potent and highly selective non-carboxylic acid, non-hydantoin inhibitors of AR yet described (IC50, 1 nM; ED90 vs sciatic nerve sorbitol and fructose, respectively, 0.8 and 4.0 mg/kg). In rats, its oral bioavailability is 98% and it has a favorable plasma t(1/2) (26 +/- 3 h).

  DOI：

  10.1021/jm050462t
• 作为产物：
  描述：

  1-(4-氟苯基)-2-苯氧基乙酮 在 Amberlyst 15 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 3-(4-fluorophenyl)benzofuran
  参考文献：
  名称：

  使用聚合物支持的试剂三步合成一系列取代的苯并呋喃

  摘要：

  通过用聚合物负载的溴化吡啶鎓过溴化物（PSPBP）将苯乙酮溴化为α-溴苯乙酮，可以实现一种有效的组合方法，以取代3-苯基苯并呋喃。随后使用1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD-P）将所得的溴化物彻底替换为苯酚，并使用Amberlyst 15将所得的α-苯氧基乙酰苯酮环化脱水，得到的纯产品不含需要任何色谱纯化步骤。

  DOI：

  10.1039/a904384e

文献信息

• Redox‐Neutral Coupling between Two C(sp ³ )−H Bonds Enabled by 1,4‐Palladium Shift for the Synthesis of Fused Heterocycles
  作者：Ronan Rocaboy、Ioannis Anastasiou、Olivier Baudoin

  DOI：10.1002/anie.201908460

  日期：2019.10.7

  secondary C-H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C-H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3 )-C(sp3 ) bonds.

  通过从三取代的芳基溴化物进行的1,4-Pd转移，可以使两个C（sp3）-H键形成一个C（sp3）-C（sp3）键进行分子内偶联。与大多数C（sp3）-C（sp3）交叉脱氢偶联相反，该反应在氧化还原中性条件下进行，其中C-Br键充当内部氧化剂。此外，它允许两个中等酸性的伯或仲CH键之间的偶联，其在一侧与氧或氮原子相邻，而在另一侧为苄基或与羰基相邻。从易于获得的邻溴苯酚和苯胺前体中获得了各种有价值的稠合杂环。第二个CH键裂解成功地被羰基插入取代，以生成其他类型的C（sp3）-C（sp3）键。
• Electrochemical Oxidative [4+2] Annulation for the π‐Extension of Unfunctionalized Heterobiaryl Compounds
  作者：Xia Hu、Lei Nie、Guoting Zhang、Aiwen Lei

  DOI：10.1002/anie.202003656

  日期：2020.8.24

  biological activities, regioselective access to fused aromatic compounds is significantly important in the field of organic materials and pharmaceutical science. Herein, we developed electrochemical oxidative [4+2] annulation reactions of heterobiaryl compounds with alkynes or alkenes, leading to the formation of several polycyclic heteroaromatic compounds. This electrosynthetic methodology serves for

  考虑到它们独特的电子特性和多样的生物活性，在有机材料和药物科学领域中，区域选择性地获得稠合的芳族化合物非常重要。在本文中，我们开发了杂联芳基化合物与炔烃或烯烃的电化学氧化[4 + 2]环氧化反应，从而导致形成多种多环杂芳族化合物。这种电合成方法可用于未官能化杂二芳基化合物的直接π延伸。消除了对其他氧化剂和原料预官能化的要求。通过原位产生杂二芳基自由基阳离子中间体，可以以高收率和优异的区域选择性获得各种稠合的芳族化合物。
• Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl Halides to Aryl Ketones for the Synthesis of Benzofuran Derivatives
  作者：Chen-Liang Deng、Xiao-Rui Zhu

  DOI：10.1055/s-0040-1706662

  日期：2021.5

  A nickel-catalyzed intramolecular nucleophilic addition reaction of aryl halides to aryl ketones for the formation of benzofuran derivatives has been developed. A number of substrates bearing electron-donating or electron-withdrawing groups were subjected to the standard reaction conditions, giving the corresponding products in moderate to good yields.

  已经开发了镍催化的芳基卤化物与芳基酮的分子内亲核加成反应，以形成苯并呋喃衍生物。使许多带有给电子或吸电子基团的底物经受标准反应条件，以中等至良好的产率得到相应的产物。
• Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
  作者：Zhanwei Ma、Min Zhou、Lin Ma、Min Zhang

  DOI：10.1177/1747519820907244

  日期：2020.7

  acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare

  由伊顿试剂（五氧化二磷-甲磺酸）促进的 α-苯氧基酮的环脱水用于在温和条件下以中等至优异的产率制备 3-取代或 2,3-二取代的苯并呋喃。该方法提供了从容易获得的起始材料（如苯酚和 α-溴酮）中轻松获得苯并呋喃的途径。反应效率高，这归功于伊顿试剂良好的反应性和流动性。该反应可用于制备萘并呋喃香豆素、苯并噻吩和苯并吡喃。
• Direct Arylation of Benzo[<i>b</i>]furan and Other Benzo-Fused Heterocycles
  作者：Toan Dao-Huy、Maximilian Haider、Fabian Glatz、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1002/ejoc.201403125

  日期：2014.12

  The direct arylation of benzo[b]furan, benzo[b]thiophene, and indole has been studied by using aromatic bromides as the aryl source. The protocol employing common reagents and a Pd catalyst has led to the regioselective arylation of these heterocycles at the 2-position. A range of functional groups were tolerated, providing quick access to a variety of arylated benzo-fused heterocycles that would be

  苯并[b]呋喃，苯并[b]噻吩和吲哚的直接芳基化已通过使用芳族溴化物作为芳基来源进行了研究。使用常用试剂和Pd催化剂的方案已导致这些杂环在2位的区域选择性芳基化。可以容忍一系列官能团，从而可以快速访问各种芳基化的苯并稠合杂环，这些杂环可以使用经典合成策略更精细地访问。这是对苯并[b]呋喃直接芳基化的首次系统研究。