6-(benzyloxy)-2-(phenyl)benzofuran | 24534-38-1

• 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: 6-(benzyloxy)-2-(phenyl)benzofuran
• 英文别名: 6-Benzyloxy-2-phenylbenzofuran；2-phenyl-6-phenylmethoxy-1-benzofuran
• CAS: 24534-38-1
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: NNTVOYSIQRRHBU-UHFFFAOYSA-N

物化性质

• 沸点：
  466.6±30.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)-2-(phenyl)benzofuran 在 四氯化钛 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-phenylbenzofuran-6-ol
  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：

  苄基三苯基氯化膦 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成 6-(benzyloxy)-2-(phenyl)benzofuran
  参考文献：
  名称：

  3-取代亚胺-6-羟基-苯并呋喃衍生物的合成及抗菌性能评价

  摘要：

  化学合成了一系列3-取代的亚胺-6-羟基-苯并呋喃衍生物，并对其进行了生物学评估，以作为对白色念珠菌，大肠杆菌，金黄色葡萄球菌，耐甲氧西林的金黄色葡萄球菌和枯草芽孢杆菌的抗菌和抗真菌剂。与使用MIC 80的阳性对照（头孢他啶）相比，大多数化合物对革兰氏阳性菌均表现出选择性的抗菌活性，而四种化合物对耐甲氧西林的金黄色葡萄球菌显示出极大的抗菌活性。 = 12.5–25μg/ mL。结构-活性关系研究表明，C-6位的游离羟基对于抗菌活性至关重要，而C-3位的芳香亚胺片段也大大提高了抗菌活性。

  DOI：

  10.1007/s00044-016-1694-8

文献信息

• 苯并呋喃类化合物及其制备、用途
  申请人：上海交通大学

  公开号：CN104478836B

  公开（公告）日：2017-06-13

  本发明涉及一种苯并呋喃类化合物及其制备、用途，其结构式如式(I)所示：其中，R1、R2、R4分别选自氢、C1‑C5的烷基、硝基、卤素、酯基、羟基、氨基、酰胺基或烷氧基；R3为氢、C1‑C5的烷基、苄基、芳香基或杂芳香基。本发明还涉及所述苯并呋喃化合物在抑制革兰氏阳性菌上的应用。本发明以3‑酮肟取代基苯并呋喃结构芳环为中心，建立和优化化合物的制备方法，并对制备的新型化合物进行抑菌筛选实验，通过初步抑菌试验确认所制备的化合物具有广谱的抑菌活性。
• A practicable environmentally benign one-pot synthesis of 2-arylbenzofurans at room temperature
  作者：Lian-Yan Liao、Gang Shen、Xue Zhang、Xin-Fang Duan

  DOI：10.1039/c2gc16181h

  日期：——

  An environmentallyfriendly one-pot synthesis of 2-arylbenzofurans under ambient temperature has been developed. It features an ortho-hydroxyl group assisted Wittig reaction of substituted salicylaldehyde followed by an in situ oxidative cyclization. Its advantages include readily available and non-hazardous materials, benign reaction conditions (room temperature, green solvent and one-pot manner), easy work-up and high overall yields. Utilizing this methodology, various 2-aryl-benzofurans including four natural products have been synthesized.

  我们开发出了一种在常温下环保型单锅合成 2-芳基苯并呋喃的方法。其特点是取代水杨醛的正羟基辅助维蒂希反应，然后原位氧化环化。其优点包括：材料易得且无害、反应条件温和（室温、绿色溶剂和单锅方式）、易于操作和总产率高。利用这种方法合成了各种 2-芳基苯并呋喃，包括四种天然产物。
• Synthesis and antimicrobial evaluation of 3-methanone-6-substituted-benzofuran derivatives
  作者：Jingbao Liu、Faqin Jiang、Xizhen Jiang、Wei Zhang、Jingjing Liu、Wenlu Liu、Lei Fu

  DOI：10.1016/j.ejmech.2012.05.013

  日期：2012.8

  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.
• Synthesis and antimicrobial evaluation of 3-substituted-imine-6-hydroxy-benzofuran derivatives
  作者：Wan He、Buzhe Xu、Jian Bao、Xinxian Deng、Wenlu Liu、Yong Zhang、Faqin Jiang、Lei Fu

  DOI：10.1007/s00044-016-1694-8

  日期：2016.11

  A series of 3-substituted-imine-6-hydroxy-benzofuran derivatives were chemically synthesized and biologically evaluated as antibacterial and antifungal agents against Candida albicans, Escherichia coli, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and Bacillus subtilis. Most compounds showed a selective antibacterial activity to gram-positive bacteria and four compounds revealed

  化学合成了一系列3-取代的亚胺-6-羟基-苯并呋喃衍生物，并对其进行了生物学评估，以作为对白色念珠菌，大肠杆菌，金黄色葡萄球菌，耐甲氧西林的金黄色葡萄球菌和枯草芽孢杆菌的抗菌和抗真菌剂。与使用MIC 80的阳性对照（头孢他啶）相比，大多数化合物对革兰氏阳性菌均表现出选择性的抗菌活性，而四种化合物对耐甲氧西林的金黄色葡萄球菌显示出极大的抗菌活性。 = 12.5–25μg/ mL。结构-活性关系研究表明，C-6位的游离羟基对于抗菌活性至关重要，而C-3位的芳香亚胺片段也大大提高了抗菌活性。