2-(2-methoxybenzylidene)benzofuran-3(2H)-one | 61370-67-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 2-(2-methoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 232-(2-methoxybenzylidene)benzofuran-3(2H)-one；2-[(2-Methoxyphenyl)methylidene]-1-benzofuran-3(2H)-one；2-[(2-methoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 61370-67-0
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: PAXAAXXKMIUQEF-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  419.1±45.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-methoxybenzylidene)benzofuran-3(2H)-one 在 四氯化钛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 methyl 4-(2-methoxyphenyl)benzofuro[3,2-b]pyridine-3-carboxylate
  参考文献：
  名称：

  从金酮衍生的 α,β-不饱和亚胺和活化的末端炔烃以多样性为导向合成苯并呋喃 [3,2-b] 吡啶衍生物

  摘要：

  介绍了一种由三乙胺介导的金酮衍生的 α,β-不饱和亚胺和活化的末端炔烃的有效环化反应，该反应能够以高产率轻松合成 1,4-二氢苯并呋喃 [3,2- b ] 吡啶。当三乙胺的亲核试剂被三苯基膦取代时，获得了另一类与额外的丙烯酸酯基序相连的 1,4-二氢苯并呋喃 [3,2- b ] 吡啶。这两种类型的 1,4-二氢苯并呋喃 [3,2- b ] 吡啶可以在 DBU 存在下芳构化以提供苯并呋喃 [3,2- b ] 吡啶，也可以通过一锅法获得。

  DOI：

  10.1039/d1cc02477a
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one 在 吡啶 、 mercury(II) diacetate 作用下， 反应 1.0h， 以75%的产率得到2-(2-methoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

  摘要：

  A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.02.009

文献信息

• Divergent synthesis of flavones and aurones via base-controlled regioselective palladium catalyzed carbonylative cyclization
  作者：Shan Xu、Huaming Sun、Mengyuan Zhuang、Shaohua Zheng、Yajun Jian、Weiqiang Zhang、Ziwei Gao

  DOI：10.1016/j.mcat.2018.03.021

  日期：2018.6

  A regioselective approach for construction of 5-membered and 6-membered flavonoid is established by Pd catalyzed carbonylative cyclization of 2-iodophenol with terminal alkynes using different amine bases under mild reaction condition. The catalytic experiments found that piperazine preferentially accelerate 6-endo cyclization, and triethylamine mediated Pd catalyzed 5-exo cyclization. Under optimized

  在温和的反应条件下，使用不同的胺碱，通过钯催化的2-碘苯酚与末端炔烃的羰基化环化反应，建立了一种构建5元和6元类黄酮的区域选择性方法。催化实验发现，哌嗪优先促进6-内环化，三乙胺介导的Pd催化5-外环化。在优化的反应条件下，Pd催化的羰基化方案成功地以优异的收率和区域选择性应用于39个实例的各种结构。
• Stereoselective synthesis of ε-lactones or spiro-heterocycles through NHC-catalyzed annulation: divergent reactivity by catalyst control
  作者：Min Wang、Zi-Qiang Rong、Yu Zhao

  DOI：10.1039/c4cc07788a

  日期：——

  NHC-catalyzed divergent annulation of enals with heterocyclic enones was developed to produce benzofuran/indole-containing ε-lactones or spiro-heterocycles in a highly diastereo- and enantioselective fashion.

  NHC催化的烯醛与杂环烯酮的分岔环化反应被开发出来，以高度对映选择性和对映选择性的方式产生苯并呋喃/吲哚含有的ε-内酯或螺环杂环化合物。
• An easy and practical approach to access multifunctional cylcopentadiene- and cyclopentene-spirooxindoles <i>via</i> [3 + 2] annulation
  作者：Prakash K. Warghude、Abhijeet S. Sabale、Ruchi Dixit、Kumar Vanka、Ramakrishna G. Bhat

  DOI：10.1039/d1ob00514f

  日期：——

  A highly regioselective [3 + 2] annulation of Morita–Baylis–Hillman (MBH) carbonates of isatin with aurone/thioaurone is developed.

  一种高区域选择性的Morita-Baylis-Hillman（MBH）碳酸酯与黄酮/硫代黄酮的[3 + 2]环化反应被开发出来。
• Dinuclear zinc-catalyzed enantioselective formal [3 + 2] cycloaddition of <i>N</i>-2,2,2-trifluoroethylisatin ketimines with low reactivity aurone derivatives
  作者：Rui-Li Wang、Shi-Kun Jia、Ya-Jun Guo、Yang Yi、Yuan-Zhao Hua、Hui-Jie Lu、Min-Can Wang

  DOI：10.1039/d1ob01599k

  日期：——

  Highly enantioselective formal [3 + 2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with aurone derivatives of low reactivity using chiral dinuclear zinc catalysts has been developed via a Brønsted base and Lewis acid cooperative activation model. These transformations involving a domino Michael/Mannich reaction sequence led to efficient construction of a range of chiral spiro[benzofuran-pyrrolidine]

  已经通过布朗斯台德碱和路易斯酸协同活化模型开发了使用手性双核锌催化剂对N -2,2,2-三氟乙基芴酮亚胺与低反应性的奥罗酮衍生物进行高度对映选择性的形式 [3 + 2] 环加成反应。这些涉及多米诺迈克尔/曼尼希反应序列的转化导致一系列手性螺[苯并呋喃-吡咯烷]支架以高产率（高达 95%）和良好的对映选择性（高达 99% ee）。
• Three-component acyloxylation of diazo compounds with carboxylic acids and azadienes
  作者：Meng-Ling Lin、Ting Zheng、Hao Liu、Ying-Xu Wang、Lin Dong

  DOI：10.1039/d2ob02133a

  日期：——

  Despite many studies on benzofuran-derived azadiene being reported, multi-component studies have scarcely been reported on this heterocyclic skeleton. The first cascade three-component acyloxylation of diazos with acids and azadienes has been reported under mild conditions. The reaction is applicable to various (A/A) diazo compounds, generating diverse complex benzofuran derivatives.

  尽管报道了许多关于苯并呋喃衍生的氮杂二烯的研究，但关于这种杂环骨架的多组分研究几乎没有报道。已经报道了在温和条件下重氮化合物与酸和氮杂二烯的第一次级联三组分酰氧基化反应。该反应适用于各种（A/A）重氮化合物，生成多种复杂的苯并呋喃衍生物。