5-methoxy-2,3-diphenylbenzofuran | 14770-95-7

• 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: 5-methoxy-2,3-diphenylbenzofuran
• 英文别名: 5-Methoxy-2,3-diphenyl-1-benzofuran
• CAS: 14770-95-7
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: KSBPSNSDSUSMDE-UHFFFAOYSA-N

物化性质

• 熔点：
  89 °C
• 沸点：
  430.9±33.0 °C(Predicted)
• 密度：
  1.151±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：
  0.05
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯乙酮肟 在 三氟甲磺酸 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.5h， 生成 5-methoxy-2,3-diphenylbenzofuran
  参考文献：
  名称：

  苯酚和萘酚区域选择性无过渡金属催化 2H-氮丙啶开环；一锅法获得苯并呋喃和萘并呋喃

  摘要：

  苯并呋喃和萘并呋喃衍生物是由容易获得的酚和萘酚合成的。 2 H-氮丙啶的区域选择性开环，然后使用催化量的布朗斯台德酸进行原位芳构化，确立了该方法的新颖性。一系列 2 H-氮丙啶与各种酚、1-萘酚和 2-萘酚的参与显示了该方案的通用性。深入的密度泛函理论计算揭示了模型反应的中间体和过渡态能量的反应机理。还通过计算机建模提出了该机制的替代途径。

  DOI：

  10.1021/acs.joc.3c01266

文献信息

• Au-catalyzed synthesis of benzofurans from phenols and alkynes using molecular oxygen
  作者：Jinqiang Liao、Pengfeng Guo、Qinlin Chen

  DOI：10.1016/j.catcom.2016.01.009

  日期：2016.3

  An efficient Au-catalyzed transformation for the synthesis of benzofurans from phenols and alkynes using molecular oxygen has been developed. The reaction proceeds smoothly with commercially available, eco-friendly oxidant and affords the products in moderate to good yields. This reaction is a facile approach for the formation of C − C and C–O bonds.

  已经开发出一种利用分子氧从苯酚和炔烃合成苯并呋喃的有效金催化转化方法。使用市售的生态友好型氧化剂可使反应平稳进行，并以中等至良好的产率提供产物。该反应是形成C-C和C-O键的简便方法。
• Facile synthesis of benzofurans via copper-catalyzed aerobic oxidative cyclization of phenols and alkynes
  作者：Wei Zeng、Wanqing Wu、Huanfeng Jiang、Liangbin Huang、Yadong Sun、Zhengwang Chen、Xianwei Li

  DOI：10.1039/c3cc42326c

  日期：——

  synthesis of polysubstituted benzofurans using a copper catalyst and molecular oxygen from phenols and alkynes in a one-pot procedure has been reported. The transformation consists of a sequential nucleophilic addition of phenols to alkynes and oxidative cyclization. A wide variety of phenols and alkynes can be used in the same manner.

  已经报道了通过一锅法使用铜催化剂和来自苯酚和炔烃的分子氧的区域选择性合成多取代的苯并呋喃。该转化由苯酚向炔烃的顺序亲核加成和氧化环化组成。各种苯酚和炔烃可以相同的方式使用。
• Direct Access to Benzo[<i>b</i>]furans through Palladium-Catalyzed Oxidative Annulation of Phenols and Unactivated Internal Alkynes
  作者：Malleswara Rao Kuram、M. Bhanuchandra、Akhila K. Sahoo

  DOI：10.1002/anie.201210217

  日期：2013.4.22

  2,3‐Disubstituted benzo[b]furans are prepared in one step from commercially available phenols and readily accessible unactivated internal alkynes (see scheme). This Pd‐catalyzed oxidative annulation has a broad substrate scope and allows access to a wide range of benzo[b]furans.

  2,3-二取代的苯并[ b ]呋喃一步一步由市售的苯酚和易于获得的未活化内部炔烃制得（参见方案）。这种Pd催化的氧化环化具有广泛的底物范围，并允许使用各种苯并[ b ]呋喃。
• Sequential One-Pot Synthesis of 3-Arylbenzofurans from <i>N</i>-Tosylhydrazones and Bromophenol Derivatives
  作者：Diana Lamaa、Camille Hauguel、Hsin-Ping Lin、Estelle Messe、Vincent Gandon、Mouad Alami、Abdallah Hamze

  DOI：10.1021/acs.joc.0c01835

  日期：2020.11.6

  A divergent and efficient one-pot sequence allowing direct access to 3-arylbenzofuran derivatives has been developed. The process, involving N-tosylhydrazones and bromophenols, proceeds via a palladium-catalyzed Barluenga–Valdés cross-coupling, followed by an aerobic, copper-catalyzed, radical cyclization to form Csp2–Csp2 and O–Csp2 bonds. 3-Arylated benzofurans bearing various substituents were obtained

  已经开发出允许直接获得3-芳基苯并呋喃衍生物的发散且有效的一锅序列。该过程涉及N-甲苯磺酰hydr和溴酚，通过钯催化的Barluenga-Valdés交叉偶联进行，然后进行需氧，铜催化的自由基环化，形成Csp 2 -Csp 2和O-Csp 2键。获得具有各种取代基的3-丙烯酸化的苯并呋喃，具有良好至优异的产率（高达90％）。机理研究强烈支持环化步骤的根本过程。
• Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis
  作者：Xin Fan、Huaiyu He、Jiao Li、Guoyong Luo、Yuanyuan Zheng、Jian-Kang Zhou、Juan He、Wenchen Pu、Yun Zhao

  DOI：10.1016/j.bmc.2019.04.028

  日期：2019.6

  Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1) participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5) and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29) as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.