5-methoxy-3-(p-tolyl)benzofuran | 1189144-70-4

• 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: 5-methoxy-3-(p-tolyl)benzofuran
• 英文别名: 5-Methoxy-3-(4-methylphenyl)-1-benzofuran
• CAS: 1189144-70-4
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: AEKKGKUSPCCSIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  5-methoxy-3-(p-tolyl)benzofuran 在 氢溴酸 、 乙酸酐 作用下， 生成 3-p-tolylbenzofuran-5-ol
  参考文献：
  名称：

  天然丹参酮状杂环稠合的邻-quinones从区域选择性狄尔斯-阿尔德反应的合成和细胞毒性评价

  摘要：

  通过IBX氧化-环加成-芳构化方法，从容易获得的苯并呋喃醇和N-取代的二烯中合成了一系列新的天然丹参酮样氧杂环稠合的邻醌衍生物。N-二烯的区域特异性Diels–Alder环加成反应可通过多种亲双烯体有效实现。发现通过控制芳构化条件可以保留或消除分子中的酰胺部分。选定的氧杂环稠合的邻醌以及几种硫杂环稠合的邻醌我们评估了之前获得的对苯二酚对不同癌细胞系的细胞毒性，并讨论了结构-活性关系（SAR）。

  DOI：

  10.1016/j.ejmech.2009.04.016
• 作为产物：
  描述：

  2-(4-Methoxyphenoxy)-1-(4-methylphenyl)ethanone 在 Amberlyst 15 作用下， 以 甲苯 为溶剂， 生成 5-methoxy-3-(p-tolyl)benzofuran
  参考文献：
  名称：

  天然丹参酮状杂环稠合的邻-quinones从区域选择性狄尔斯-阿尔德反应的合成和细胞毒性评价

  摘要：

  通过IBX氧化-环加成-芳构化方法，从容易获得的苯并呋喃醇和N-取代的二烯中合成了一系列新的天然丹参酮样氧杂环稠合的邻醌衍生物。N-二烯的区域特异性Diels–Alder环加成反应可通过多种亲双烯体有效实现。发现通过控制芳构化条件可以保留或消除分子中的酰胺部分。选定的氧杂环稠合的邻醌以及几种硫杂环稠合的邻醌我们评估了之前获得的对苯二酚对不同癌细胞系的细胞毒性，并讨论了结构-活性关系（SAR）。

  DOI：

  10.1016/j.ejmech.2009.04.016

文献信息

• Nickel catalyzed intramolecular oxidative coupling: synthesis of 3-aryl benzofurans
  作者：Sakshi Aggarwal、Dasari Srinivas、Chinnabattigalla Sreenivasulu、Gedu Satyanarayana

  DOI：10.1039/d0ra03071f

  日期：——

  transition metal-catalyzed reactions. Herein we have developed nickel-catalyzed synthesis of 3-aryl benzofurans from ortho-alkenyl phenols via intramolecular dehydrogenative coupling. Notably, simple O2 gas served as an oxidant, without using any sacrificial hydrogen acceptor. The strategy enabled the synthesis of 3-aryl benzofurans in good to excellent yields.

  最近的研究集中在过渡金属催化的反应上。在此，我们开发了通过分子内脱氢偶联从邻-烯基酚中镍催化合成 3-芳基苯并呋喃。值得注意的是，简单的 O 2气体用作氧化剂，没有使用任何牺牲的氢受体。该策略能够以良好至优异的产率合成 3-芳基苯并呋喃。
• Natural tanshinone-like heterocyclic-fused ortho-quinones from regioselective Diels–Alder reaction: Synthesis and cytotoxicity evaluation
  作者：Yu-Dong Shen、Yuan-Xin Tian、Xian-Zhang Bu、Lian-Quan Gu

  DOI：10.1016/j.ejmech.2009.04.016

  日期：2009.10

  oxoheterocyclic-fused ortho-quinone derivatives were synthesized from readily available benzofuranol and N-substituted dienes via IBX oxidation–cycloaddition–aromatization procedure. The regiospecific Diels–Alder cycloaddition reactions of N-dienes were achieved efficiently with a variety of dienophiles. It is found that the amide moiety in the molecular could be preserved or eliminated by control of the aromatization

  通过IBX氧化-环加成-芳构化方法，从容易获得的苯并呋喃醇和N-取代的二烯中合成了一系列新的天然丹参酮样氧杂环稠合的邻醌衍生物。N-二烯的区域特异性Diels–Alder环加成反应可通过多种亲双烯体有效实现。发现通过控制芳构化条件可以保留或消除分子中的酰胺部分。选定的氧杂环稠合的邻醌以及几种硫杂环稠合的邻醌我们评估了之前获得的对苯二酚对不同癌细胞系的细胞毒性，并讨论了结构-活性关系（SAR）。
• TfOH-SiO2 as an Efficient and Recyclable Catalyst for Synthesis of 3-Arylbenzofurans
  作者：Hua Zheng、Baolong Wang、Jiaxing Hu、Fanglin Zhang

  DOI：10.3987/com-15-13351

  日期：——

  A convenient process for the synthesis of 3-arylbenzofurans and their derivatives by 2-phenoxy-1-phenylethanones via TfOH-SiO2 catalyzed is developed. This method provides several advantages such as simple work-up procedure, simple post-treatment process, high yields, broad applicability, practicability, and recycling of the catalyst.
• Iodine-Mediated, Microwave-Assisted Synthesis of 1-Arylnaphthofurans via Cyclization of 1-(1′-Arylvinyl)-2-naphthols
  作者：Anil Kumar、V. Rao、Pinku Kaswan、Ganesh Shelke、Ashley Ryan、Mukund Jha

  DOI：10.1055/s-0035-1560268

  日期：——

  A metal-free, one-pot, iodine-mediated, microwave-assisted cyclization of 1-(1-arylvinyl)-2-naphthols (ortho-vinylnaphthols) into 1-arylnaphthofurans is developed. The 1-arylnaphthofurans are isolated in good to excellent yields (65-90%) using two equivalents of iodine in acetonitrile. The reactions proceed via the formation of 1-(2-iodo-1-phenylvinyl)naphthalen-2-ols as intermediates. Overall, the protocol is convenient as the reactions occur smoothly without the requirement of a transition-metal catalyst.
• 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.