2-(4-methoxyphenyl)benzofuran-6-ol | 134804-66-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-methoxyphenyl)benzofuran-6-ol
• 英文别名: 2-(4-Methoxyphenyl)-1-benzofuran-6-ol
• CAS: 134804-66-3
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: NIMJBTFKNMBUDO-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  301.7±21.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)benzofuran-6-ol 在 四氯化锡 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 (E)-1-(2-(4-methoxyphenyl)-6-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)-benzofuran-3-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 3-methanone-6-substituted-benzofuran derivatives

  摘要：

  Seventeen benzofuran derivatives were synthesized and screened for their antibacterial activities against Escherichia coli, Staphylococcus aureus, Methicillin-resistant S. aureus, Bacillus subtilis, and Pseudomonas aeruginosa. Seven of them have showed excellent antibacterial activities compared to the positive controls (Cefotaxime and Sodium Penicillin). The substitutions at C-6 and C-3 positions of these derivatives were found to greatly impact on the antibacterial activity and strains specificity, respectively. Specifically, compounds bearing a hydroxyl group at C-6 (5a, 5b, 5c and 12) offered excellent antibacterial activities against all five above-mentioned strains (MIC80 = 0.78-12.5 ug/mL), and those with imine (15) and (3, 4, 5-trimethoxyphenyl) methanone (7e), respectively, at C-3 position showed selective activity against S. aureus among five tested strains with great MIC80 values (3.12-12.5 ug/mL). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.013
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 、 溶剂黄146 、 三乙胺 、 thallium(III) nitrate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 2-(4-methoxyphenyl)benzofuran-6-ol
  参考文献：
  名称：

  Meyer, M.; Deschamps, C.; Molho, D., Bulletin de la Societe Chimique de France, 1991, # 1, p. 91 - 99

  摘要：

  DOI：

文献信息

• Regioselective Preparation of Benzo[<i>b</i>]furans from Phenols and α<i>-</i>Bromoketones
  作者：Leire Arias、Yosu Vara、Fernando P. Cossío

  DOI：10.1021/jo201841y

  日期：2012.1.6

  In this paper, a fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted

  在本文中，描述了2-和3-取代的苯并[ b ]呋喃的完全区域控制的合成。在中性氧化铝存在下，苯酚与α-溴乙酰苯之间的直接反应生成具有完全区域控制能力的2取代的苯并[ b ]呋喃。当使用碱性盐如碳酸钾时，获得了相应的2-氧代醚。由中性氧化铝促进的这些后面化合物的环化产生相应的3-取代的苯并[ b ]呋喃。使用前一种方法，可以在两个制备步骤中从商业来源获得Moracin M和其他类似物。DFT计算提供了合理的反应路径，以了解2-取代的苯并[ b ]呋喃的形成。
• Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran
  作者：Ling Zhang、Tongxiang Cao、Huanfeng Jiang、Shifa Zhu

  DOI：10.1002/anie.201915212

  日期：2020.3.16

  An unprecedented deconstructive reorganization strategy for the de novo synthesis of hydroxylated benzofurans from kojic acid- or maltol-derived alkynes is reported. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six-carbon component. Through this

  报道了一种空前的解构重组策略，用于从曲酸或麦芽酚衍生的炔烃从头合成羟基化苯并呋喃。在该反应中，同时构造了苯环和呋喃环，而曲酸或麦芽酚的吡喃酮部分被解构，然后以六碳组分重组为苯环。通过这种策略，以取代模式可调节的方式将至少一个游离羟基引入苯环，而无需进行保护-脱保护和氧化还原调节。通过这种方法，已经有效地制备了具有不同取代模式的大量羟基化苯并呋喃衍生物。
• Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with <i>N′</i> -Acyl Arylhydrazines
  作者：Jun Cao、Zi-Li Chen、Shu-Min Li、Gao-Feng Zhu、Yuan-Yong Yang、Cong Wang、Wen-Zhang Chen、Jian-Ta Wang、Ji-Quan Zhang、Lei Tang

  DOI：10.1002/ejoc.201800374

  日期：2018.6.15

  An efficient and ligand‐free palladium‐catalyzed arylation of benzofurans has been developed with N′ ‐acyl arylhydrazines as the coupling partners. This protocol features a wide functional‐group tolerance and highly regioselective products.

  已开发出一种高效且无配体的钯催化苯并呋喃芳基化反应，以 N'-酰基芳基肼作为偶联伙伴。该协议具有广泛的官能团耐受性和高度区域选择性的产品。
• Transition metal directed synthesis of moracin M, a phytoalexin of Morus alba Linn.
  作者：Inderjit S. Mann、David A. Widdowson、John M. Clough

  DOI：10.1016/s0040-4020(01)81951-7

  日期：1991.9

  2-(5-Resorcinyl)benzofurans have been synthesised by the palladium catalysed cross coupling of 2-trimethylstannyl-or 2-bromozinc benzofurans with the appropriately functionalised 5-iodoresorcinols. These were synthesised by the tri-isopropylsilyloxy directed remote (C-5) lithiation/iodination of the O,O-di(tri-isopropylsilyl)resorcinoltricarbonylchromium(0) complex. The method was applied to the synthesis

  2-（5-间苯二甲酰基）苯并呋喃是通过钯催化的2-三甲基锡烷基-或2-溴锌苯并呋喃与适当官能化的5-异戊二烯醇的交叉偶联而合成的。这些是通过O，O-二（三异丙基甲硅烷基）间苯二酚三羰基铬（0）络合物的三异丙基甲硅烷氧基定向远程（C-5）锂化/碘化合成的。该方法用于桑树桑of中草糖蛋白M a植物抗毒素的合成。
• MEYER, M.;DESCHAMPS, C.;MOLHO, D., BULL. SOC. CHIM. FR. ,(1991) N, C. 91-99
  作者：MEYER, M.、DESCHAMPS, C.、MOLHO, D.

  DOI：——

  日期：——