(4-bromophenyl)(3-methylbenzofuran-2-yl)methanone | 67534-80-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-bromophenyl)(3-methylbenzofuran-2-yl)methanone
• 英文别名: (4-bromophenyl)-(3-methyl-1-benzofuran-2-yl)methanone
• CAS: 67534-80-9
• 化学式: C₁₆H₁₁BrO₂
• mdl: MFCD12461694
• 分子量: 315.166
• InChiKey: MFZMPRRCXQKZCC-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C
• 沸点：
  403.0±30.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-bromophenyl)(3-methylbenzofuran-2-yl)methanone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 2-(p-Bromobenzoyl)-3-bromomethylbenzofuran
  参考文献：
  名称：

  Benzofuranyl- and thiophenylmethylthio-alcanecarboxylic acid derivatives

  摘要：

  苯并呋喃基和硫代苯基甲硫基烷基羧酸衍生物是通过对适当的甲基化合物进行溴化并将得到的甲基溴化物与巯基-烷基羧酸衍生物反应制备而成。这些新物质适用于作为NADPH氧化酶抑制剂用于药物，特别是用于治疗急性和慢性炎症过程。

  公开号：

  EP0551662A1
• 作为产物：
  描述：

  在 potassium phosphate 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 0.5h， 以94%的产率得到(4-bromophenyl)(3-methylbenzofuran-2-yl)methanone
  参考文献：
  名称：

  2,3-二取代的苯并A高效超声促进的合成[ b ]呋喃通过在离子液体[BMIM] BF分子内的C-C键形成4在室温下†

  摘要：

  据报道，在室温下，在离子液体[bmim] BF 4中超声有效地促进了2,3-二取代的苯并[ b ]呋喃的合成。在大气条件下，使用无水K 3 PO 4作为温和且廉价的碱，可以介导5 -exo-dig Carbanion-yne分子内环化反应，从而以优异的收率得到标题为benzo [ b ]呋喃的化合物。离子液体[bmim] BF 4既用作反应介质，又用作形成CC键的催化剂。

  DOI：

  10.1039/c2ra22355d

文献信息

• Solution-phase photochemical transformation of 2-aroylbenzofurans: addition–elimination mechanism
  作者：Pooja Jindal、Geeta Sharma、Rita Arora、Ramesh C. Kamboj

  DOI：10.1007/s11164-014-1544-6

  日期：2015.7

  An efficient conversion of 2-aroylbenzofurans into arylbenzofurylmethanols through photoreduction has been described. In these molecules, the photo transformation occurred through the initial addition of solvent followed by elimination involving γ-hydrogen abstraction. The photoproduct distribution markedly depends upon the substituent present on the benzofuran moiety.

  已经描述了通过光还原将2-芳基苯并呋喃有效转化为芳基苯并呋喃甲醇。在这些分子中，光转化是通过最初添加溶剂，然后消除涉及γ-氢提取的溶剂而发生的。光产物的分布明显取决于苯并呋喃部分上存在的取代基。
• Nickel-Catalyzed Domino Reaction of α-Aryloxyacetonitriles with Arylboronic Acids: Synthesis of 2-Aroylbenzo[<i>b</i>]furans
  作者：Subhashini V. Subramaniam、Vijaya Kumaran Dharmalingam、Anwesha Bhattacharya、Saravanan Peruncheralathan

  DOI：10.1021/acs.orglett.3c03241

  日期：2023.11.24

  We disclose the first catalytic domino reaction of α-(2-formylaryloxy)acetonitriles with arylboronic acids, yielding a range of 2-aroylbenzo[b]furans with yields of up to 93%. Ni(acac)2 serves as an effective dual catalyst. The protocol is also applicable to α-(2-acetylphenoxy)acetonitrile, giving rise to 3-methyl-2-aroylbenzo[b]furans. This domino process is efficient, additive-free, and compatible

  我们公开了 α-(2-甲酰基芳氧基)乙腈与芳基硼酸的首次催化多米诺反应，产生一系列 2-芳酰基苯并[ b ]呋喃，产率高达 93%。Ni(acac) 2是一种有效的双催化剂。该方案也适用于 α-(2-乙酰基苯氧基)乙腈，产生 3-甲基-2-芳酰基苯并[ b ]呋喃。该多米诺骨牌工艺高效、无添加剂，并且与多种芳基硼酸相容，包括带有CF 3、NO 2、CN 和CO 2 Me 基团的芳基硼酸。机理研究强调了镍催化剂促进的双重活化。
• DMAP-catalyzed cascade reaction: one-pot synthesis of benzofurans in water
  作者：Yongjia Shang、Cuie Wang、Xinwei He、Kai Ju、Min Zhang、Shuyan Yu、Jiaping Wu

  DOI：10.1016/j.tet.2010.09.095

  日期：2010.12

  A series of benzofurans were efficiently synthesized in good to excellent yields using 4-dimethylaminopyridine (DMAP) catalyzed cascade reaction between salicylaldehydes and halogenated ketones in water at 80 degrees C opened atmosphere. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Bi(OTf) ₃ ‐Mediated (4+1) Annulation of α‐Sulfonyl <i>o</i> ‐Hydroxyacetophenones with α‐Hydroxy Arylketones to Access Sulfonyl 2‐Aroylbenzofurans
  作者：Meng‐Yang Chang、Kuan‐Ting Chen

  DOI：10.1002/adsc.202100143

  日期：2021.5.18

  AbstractIn this paper, a high‐yield, facile route for the scalable synthesis of sulfonyl 2‐aroylbenzofurans via a Bi(OTf)3‐mediated intermolecular double cyclocondensation of α‐sulfonyl o‐hydroxyacetophenones with substituted α‐hydroxy arylketones under mild open‐vessel reaction conditions is described. In the overall reaction, water is generated as the only byproduct. Various metal triflate‐promoted reactions and conditions are investigated for the efficient one‐pot (4+1) annulation reaction.magnified image
• Synthesis and antimicrobial evaluation of substituted (1,1'-biphenyl)-4-yl(3-methylbenzofuran-2-yl)methanones by Suzuki cross-coupling reaction
  作者：B. J. Reddy、V. P. Reddy

  DOI：10.1134/s1070363216120410

  日期：2016.12

  A series of new substituted [1,1'-biphenyl]-4-yl(3-methylbenzofuran-2-yl)methanones was prepared by Suzuki cross-coupling from (4-bromophenyl)(3-methylbenzofuran-2-yl)methanone. The obtained compounds were assayed for their in vitro antibacterial activity against different types of bacterial strains; antifungal activity was also examined by inhibitory effect against different fungal strains.