phenyl(3-phenylbenzofuran-2-yl)methanone | 14176-44-4

• 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: phenyl(3-phenylbenzofuran-2-yl)methanone
• 英文别名: Phenyl-(3-phenyl-1-benzofuran-2-yl)methanone
• CAS: 14176-44-4
• 化学式: C₂₁H₁₄O₂
• 分子量: 298.341
• InChiKey: JZPVYYKYOJOWAT-UHFFFAOYSA-N

物化性质

• 沸点：
  502.4±43.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• 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

• 作为产物：
  描述：

  3-苯基-3H-1-苯并呋喃-2-酮 在 叔丁基过氧化氢 、 sodium carbonate 、 potassium carbonate 、 nickel dichloride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 phenyl(3-phenylbenzofuran-2-yl)methanone
  参考文献：
  名称：

  3-芳基苯并呋喃-2（3H）-酮的镍催化脱羰氧化为2-羟基二苯甲酮。

  摘要：

  我们已经开发了一种协议，可以在温和的条件下促进3-芳基苯并呋喃-2（3H）-的镍催化脱羰氧化为2-羟基二苯甲酮，这是有机合成中内酯脱羰氧化的有效方法。各种各样的底物可以进行C（O）–O / C（O）–C键裂解，以高产率产生目标产物。这些2-羟基二苯甲酮可通过酯化，环化和还原等反应转化为多种化合物。

  DOI：

  10.1021/acs.joc.0c00858

文献信息

• Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles
  作者：Julin Gong、Kun Hu、Yinlin Shao、Renhao Li、Yetong Zhang、Maolin Hu、Jiuxi Chen

  DOI：10.1039/c9ob02408e

  日期：——

  example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2

  已经开发了钯催化串联2-（2-酰基苯氧基）乙腈与芳基硼酸的串联/加成反应的第一个实例，为合成具有优异的化学选择性和广泛的官能团相容性的2-芳酰基苯并呋喃提供了新的策略。初步的机理实验表明，该串联过程涉及顺序的亲核加成，产生2-（2-酰基苯氧基）-1-苯基乙-1-酮，然后进行分子内环化。该方法也已用于2-芳酰基吲哚和强效CYP19抑制剂1-（苯并呋喃-2-基（苯基）甲基）-1H-1,2,4-三唑的合成。
• Anti-Influenza Drug Discovery: Structure−Activity Relationship and Mechanistic Insight into Novel Angelicin Derivatives
  作者：Jiann-Yih Yeh、Mohane Selvaraj Coumar、Jim-Tong Horng、Hui-Yi Shiao、Fu-Ming Kuo、Hui-Ling Lee、In-Chun Chen、Chun-Wei Chang、Wen-Fang Tang、Sung-Nain Tseng、Chi-Jene Chen、Shin-Ru Shih、John T.-A. Hsu、Chun-Chen Liao、Yu-Sheng Chao、Hsing-Pang Hsieh

  DOI：10.1021/jm901570x

  日期：2010.2.25

  By using a cell-based high throughput screening campaign,a novel angelicin derivative 6a was identified to inhibit influenza A (H1N1) virus induced Cytopathic effect in Madin-Darby canine kidney cell culture in low micromolar range. Detailed structure-activity relationship studies of 6a revealed that the angelicin scaffold is essential for activity in pharmacophore B, while meta-substituted phenyl/2-thiophene rings are optimal ill pharmacophore A and C. The optimized lead 4-methyl-9-phenyl-8-(thiophene-2-carbonyl)-furo[2,3-h]chromen-2-one (8g, IC50 = 70 nM) showed 64-fold enhanced activity compared to the high throughput screening (HTS) hit 6a. Also, 8g was found effective in case of influenza A (H3N2) and influenza B virus strains similar to approved anti-influenza drug zanamivir (4). Preliminary mechanistic studies suggest that these compounds act as anti-influenza agents by inhibiting ribonucleoprotein (RNP) complex associated activity and have the potential to be developed further, Which Could form the basis for developing additional defense against influenza pandemics.
• Palladium-Catalyzed Direct Arylation of Polysubstituted Benzofurans
  作者：Amandine Carrër、Dimitri Brinet、Jean-Claude Florent、Patricia Rousselle、Emmanuel Bertounesque

  DOI：10.1021/jo202060k

  日期：2012.2.3

  An efficient access to 2-substituted 3-arylbenzofurans through a palladium-catalyzed C3 direct arylation of 2-substituted benzofurans with aryl bromides is described. The scope and limitation of this reaction was studied. The method tolerates a variety of functional groups on the aryl halide and has been successfully extended to polysubstituted benzofurans to obtain the corresponding 3-arylbenzofurans with good to excellent yields.