2-Benzoyl-5,7-dibrombenzofuran | 75630-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Benzoyl-5,7-dibrombenzofuran
• 英文别名: 2-benzoyl-5,7-dibromobenzofuran；2-benzoyl-5,7-dibromo-benzofurane；(5,7-dibromobenzofuran-2-yl)(phenyl)methanone；5,7-dibromo-2-benzoylbenzofuran；(5,7-dibromo-benzofuran-2-yl)-phenyl ketone；(5,7-Dibrom-benzofuran-2-yl)-phenyl-keton；(5,7-Dibromo-1-benzofuran-2-yl)(phenyl)methanone；(5,7-dibromo-1-benzofuran-2-yl)-phenylmethanone
• CAS: 75630-71-6
• 化学式: C₁₅H₈Br₂O₂
• 分子量: 380.035
• InChiKey: LIOPLRFUVZPJKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-Benzoyl-5,7-dibrombenzofuran 在 羟胺 作用下， 生成 (5,7-dibromo-benzofuran-2-yl)-phenyl ketone oxime
  参考文献：
  名称：

  Mangini, Gazzetta Chimica Italiana, 1937, vol. 67, p. 39,43

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-dibromo-2-hydroxychalcone dibromide 在 氢氧化钾 作用下， 生成 2-Benzoyl-5,7-dibrombenzofuran
  参考文献：
  名称：

  Mangini, Gazzetta Chimica Italiana, 1937, vol. 67, p. 39,43

  摘要：

  DOI：

文献信息

• Intramolecular oxidative coupling: I₂/TBHP/NaN₃-mediated synthesis of benzofuran derivatives
  作者：Wengang Xu、Qingcui Li、Chuanpeng Cao、Fanglin Zhang、Hua Zheng

  DOI：10.1039/c5ob00577a

  日期：——

  A novel intramolecular oxidative coupling reaction has been established to prepare benzofuran derivatives via direct C(sp²)–H functionalization for the formation of C–O bonds. This transformation is mediated by I₂/TBHP/NaN₃ under metal-free conditions and a catalytic amount of NaN₃ plays a crucial role in the reaction.

  已建立一种新型分子内氧化偶联反应，用于通过直接C(sp²)–H官能化形成C–O键制备苯并呋喃衍生物。此转化在无金属条件下由I₂/TBHP/NaN₃介导，而催化量的NaN₃在反应中起着关键作用。
• Capuano, Lilly; Ahlhelm, Alfred; Hartmann, Herbert, Chemische Berichte, 1986, vol. 119, # 6, p. 2069 - 2074
  作者：Capuano, Lilly、Ahlhelm, Alfred、Hartmann, Herbert

  DOI：——

  日期：——
• Synthesis and anti-methicillin-resistant <i>Staphylococcus aureus</i> activity of 5,7-dibromo-2-benzoylbenzofurans alone and in combination with antibiotics
  作者：Phuong-Thuy T. Phan、Hong-Nhung T. Nguyen、Son N. Kim、Tuan-Anh N. Pham

  DOI：10.1080/00397911.2020.1855354

  日期：2021.3.4

  A series of 5,7-dibromo-2-benzoylbenzofurans were synthesized by the Rap-Stoermer condensation of 5,7-dibromosalicylaldehyde with diverse phenacyl bromides and evaluated for in-vitro antibacterial activities against methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and MRSA ATCC 33591 by agar dilution method. The synergistic effects were determined by using the agar dilution checkerboard assay. The derivatives bearing carboxylic acid functional groups exhibited reasonable activity against MRSA strains with the best MIC = 32 mu g/mL (9b, 9d). Moreover, the additive or synergistic interactions against MRSA strains was observed in six combinations (1b + cefuroxime/gentamicin, 1c + ciprofloxacin/gentamicin, 9b + gentamicin, and 9c + ciprofloxacin) with the fractional inhibitory concentration index (FICI) values in the range of 0.375-1.0. Significantly, the MICs of these antibiotics were reduced 2-4-fold. The results of the MTT assay illustrated the low mammalian cell cytotoxicity of these potent compounds.
• Microwave-mediated solvent free Rap–Stoermer reaction for efficient synthesis of benzofurans
  作者：Maddali L.N. Rao、Dheeraj K. Awasthi、Debasis Banerjee

  DOI：10.1016/j.tetlet.2006.11.077

  日期：2007.1

  The Rap-Stoermer reaction of salicylaldehydes with diverse phenacyl bromide and phenacyl iodides proceeded cleanly to afford various functionalized benzofurans in excellent yields under base-mediated solvent free microwave irradiation conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• Donnely, John A.; Quigley, Killian, Journal of the Chemical Society. Perkin transactions I, 1980, p. 1299 - 1305
  作者：Donnely, John A.、Quigley, Killian

  DOI：——

  日期：——