7-methoxy-3-phenylbenzofuran | 14385-50-3

• 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: 7-methoxy-3-phenylbenzofuran
• 英文别名: 7-Methoxy-3-phenyl-benzofuran；7-methoxy-3-phenyl-1-benzofuran
• CAS: 14385-50-3
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: QFTGEJQVBJWOPO-UHFFFAOYSA-N

物化性质

• 沸点：
  364.0±30.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 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：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-phenylbenzofuran 、 二氧化氮 、 水 在 乙醚 、 水 、 氯化钠 、 silica gel 、 氯仿 、 乙醇 作用下， 以 溶剂黄146 、 乙醚 、 氯仿 为溶剂， 反应 1.5h， 以to give yellow crystals of 7-methoxy-2-nitro-3-phenylbenzofuran, m.p. 160°-161° C.的产率得到7-methoxy-2-nitro-3-phenylbenzofuran
  参考文献：
  名称：

  Use of certain 2-nitro-3-phenyl-alkoxybenzofurans in inhibiting growth

  摘要：

  某些烷氧基取代的2-硝基-3-苯基苯并呋喃通过2-卤代-3-苯基苯并呋喃与硝化剂的交换反应制备，并发现其具有抗微生物活性。

  公开号：

  US04022908A1
• 作为产物：
  描述：

  2-(2-甲氧基苯氧基)-1-苯基乙酮 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到7-methoxy-3-phenylbenzofuran
  参考文献：
  名称：

  BCl3-promoted synthesis of benzofurans

  摘要：

  Lewis acidic nature of boron trichloride (BCl3) to coordinate to the carbonyl functionality was exploited for the synthesis of benzofurans via dehydrative cyclization. This mild and efficient procedure allowed for facile access to a number Of highly Substituted benzofurans in a regioselective manner. The Structural requirement for the successful cyclodehydration was examined in the cases, where competitive demethylation could occur. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.034

文献信息

• Benzofurans from Benzophenones and Dimethylacetamide: Copper-Promoted Cascade Formation of Furan O1C2 and C2C3 Bonds Under Oxidative Conditions
  作者：María J. Moure、Raul SanMartin、Esther Dominguez

  DOI：10.1002/anie.201108513

  日期：2012.3.26

  benzofuran core through a cascade of copper‐catalyzed processes wherein the key carbon atom comes from the dimethylacetamide (DMA) solvent. Strong evidence for the participation of a Wacker cyclization catalyzed solely by copper is provided, not only in the title reaction from benzophenones but also from 2‐hydroxy‐α‐arylstyrene derivatives.

  DMA捐赠：乙酸铜（II）和8-羟基喹啉通过一系列铜催化过程来促进苯并呋喃核的形成，其中关键碳原子来自二甲基乙酰胺（DMA）溶剂。有力的证据证明了仅由铜催化的瓦克环化反应不仅在二苯甲酮的标题反应中，而且在2-羟基-α-芳基苯乙烯衍生物的反应中也有提供。
• 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.
• US4022908A
  申请人：——

  公开号：US4022908A

  公开（公告）日：1977-05-10
• BCl3-promoted synthesis of benzofurans
  作者：Ikyon Kim、Sei-Hee Lee、Sunkyung Lee

  DOI：10.1016/j.tetlet.2008.09.034

  日期：2008.11

  Lewis acidic nature of boron trichloride (BCl3) to coordinate to the carbonyl functionality was exploited for the synthesis of benzofurans via dehydrative cyclization. This mild and efficient procedure allowed for facile access to a number Of highly Substituted benzofurans in a regioselective manner. The Structural requirement for the successful cyclodehydration was examined in the cases, where competitive demethylation could occur. (C) 2008 Elsevier Ltd. All rights reserved.
• Use of certain 2-nitro-3-phenyl-alkoxybenzofurans in inhibiting growth
  申请人：Riker Laboratories, Inc.

  公开号：US04022908A1

  公开（公告）日：1977-05-10

  Certain alkoxy-substituted-2-nitro-3-phenylbenzofurans are prepared by the exchange reaction of 2-halo-3-phenylbenzofurans with nitrating agents and are found to be useful antimicrobial agents.

  某些烷氧基取代的2-硝基-3-苯基苯并呋喃通过2-卤代-3-苯基苯并呋喃与硝化剂的交换反应制备，并发现其具有抗微生物活性。