4-((3-oxobenzofuran-2(3H)-ylidene)methyl)benzonitrile | 73139-89-6

• 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: 4-((3-oxobenzofuran-2(3H)-ylidene)methyl)benzonitrile
• 英文别名: 2-((3-oxobenzofuran-2(3H)-ylidene)methyl)benzonitrile；2-(4-Cyanobenzyliden)cumaranon(3)；4-(3-oxo-3H-benzofuran-2-ylidenemethyl)-benzonitrile；4-[(3-oxo-1-benzofuran-2-ylidene)methyl]benzonitrile
• CAS: 73139-89-6
• 化学式: C₁₆H₉NO₂
• 分子量: 247.253
• InChiKey: MCJKLANDGDSPRN-UHFFFAOYSA-N

物化性质

• 熔点：
  212.5-215.0 °C(Solv: ethanol (64-17-5))
• 沸点：
  464.8±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-((3-oxobenzofuran-2(3H)-ylidene)methyl)benzonitrile 在 二氢吡啶 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以1.6 g的产率得到4-((3-oxo-2,3-dihydrobenzofuran-2-yl)methyl)benzonitrile
  参考文献：
  名称：

  钯催化脱羧脱芳基不对称烯丙基烷基化的光学活性黄酮类分子

  摘要：

  借助一类新发现的带有手性环烷烃骨架的 Trost 型双膦配体，Pd 催化的苯并呋喃脱羧脱芳基不对称烯丙基烷基化 (AAA) 高效 [0.2-1.0 mol% Pd2(dba)3 /L]，良好的通用性和高对映选择性（> 30 个实例，82-99% 产率和 90-96% ee）。此外，公开了以前无法到达的黄酮类化合物的面向多样性的合成（DOS）。它具有可靠且可扩展的新开发的 Tsuji-Trost-Stoltz AAA 序列、Wacker-Grubbs-Stoltz 氧化、安息香内缩合和共轭加成，可有效构建具有挑战性的紧凑型具有连续立体中心的环戊二烯[b]苯并呋喃支架。该策略为开发基于黄格兰的药物提供了新途径。

  DOI：

  10.1021/jacs.0c05113
• 作为产物：
  描述：

  4-<3-(2-Hydroxy-phenyl)-3-oxo-propen-(1)-yl>-benzonitril 在 吡啶 、 mercury(II) diacetate 作用下， 反应 1.0h， 以75%的产率得到4-((3-oxobenzofuran-2(3H)-ylidene)methyl)benzonitrile
  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

• Highly Regio‐, Diastereo‐, and Enantioselective Synthesis of Tetrahydroazepines and Benzo[ <i>b</i> ]oxepines through Palladium‐Catalyzed [4+3] Cycloaddition Reactions
  作者：Barry M. Trost、Zhijun Zuo

  DOI：10.1002/anie.201911537

  日期：2020.1.13

  A novel Pd0 -catalyzed asymmetric [4+3] annulation reaction of two readily accessible starting materials has been developed for building seven-membered heterocyclic architectures. The potential [3+2] side pathway could be suppressed though fine tuning of the conditions. A broad scope of cycloaddition donors and acceptors participated in the transformation with excellent chemo-, regio-, diastereo-,

  已经开发出一种新颖的Pd0催化的两种易于获取的起始材料的不对称[4 + 3]环化反应，用于构建七元杂环体系。通过条件的微调可以抑制潜在的[3 + 2]旁通路。大量的环加成供体和受体以优异的化学选择性，区域选择性，非对映异构体和对映体选择性参与了转化，从而形成了有价值的四氢a庚因和苯并[b]氧杂环丁烷。
• Enantioselective synthesis of spirocyclic tetrahydrothiophene derivatives bearing a benzofuran-3(2H)-one scaffold. Unusual supramolecular crystal structure with high Z′
  作者：Dorota Kowalczyk、Jakub Wojciechowski、Łukasz Albrecht

  DOI：10.1016/j.tetlet.2016.04.111

  日期：2016.6

  Herein, we report our studies on the enantioselective synthesis of spirocyclic tetrahydrothiophene derivatives bearing a benzofuran-3(2H)-one scaffold. The developed method utilizes 2-arylidenebenzofuran-3(2H)-ones and 2-thioacetaldehyde, generated in situ from 1,4-dithiane-2,5-diol, as starting materials and proceeds in a cascade manner involving a thio-Michael-aldol reaction sequence. The absolute

  在本文中，我们报告了我们对带有苯并呋喃3（2 H）-一个支架的螺环四氢噻吩衍生物的对映选择性合成的研究。所开发的方法利用从1,4-二噻吩-2,5-二醇原位生成的2-芳基苯并呋喃-3（2 H）-one和2-硫代乙醛作为原料，并以涉及硫代-迈克尔的级联方式进行-醛醇缩合反应序列。通过单晶X射线分析确定获得的四氢噻吩的绝对构型。在晶体中发现异常高的Z'晶体堆积。
• Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate
  作者：Huanzhen Ni、Zhaoyuan Yu、Weijun Yao、Yu Lan、Nisar Ullah、Yixin Lu

  DOI：10.1039/c7sc02176c

  日期：——

  Catalyst-controlled regiodivergent [3 + 2] annulations of aurones and allenoates have been developed. When a dipeptide phosphine catalyst with an L-D- configuration was employed, α-selective [3 + 2] annulation products could be obtained with good regioselectivities and enantioselectivities. With the employment of L-L- dipeptide phosphines, γ-selective annulation products could be selectively obtained

  已经开发了催化剂控制的金氧和脲基甲酸酯的区域发散[3 + 2]环。当使用具有LD-构型的二肽膦催化剂时，可以获得具有良好区域选择性和对映选择性的α-选择性[3 + 2]环化产物。随着LL的雇用-二肽膦，可以以优异的对映选择性选择性地获得γ-选择性环化产物。通过简单地调节催化剂构型，可以容易地制备具有芳基或烷基取代基的宽范围的α-选择性或γ-选择性螺环苯并呋喃酮。DFT计算表明，二肽膦的构象会影响氢键相互作用或畸变能，从而导致过渡态中能量的微分，并解释了所观察到的区域选择性。
• Diversity-oriented synthesis of benzofuro[3,2-<i>b</i>]pyridine derivatives from aurone-derived α,β-unsaturated imines and activated terminal alkynes
  作者：Bin Cheng、Hui Li、Xuecheng Zhu、Xinping Zhang、Yixuan He、Haiyan Sun、Taimin Wang、Hongbin Zhai

  DOI：10.1039/d1cc02477a

  日期：——

  facile synthesis of 1,4-dihydrobenzofuro[3,2-b]pyridines in high yields. When the nucleophile of triethylamine was replaced with triphenylphosphine, another class of 1,4-dihydrobenzofuro[3,2-b]pyridines tethered with an additional acrylate motif were obtained instead. These two types of 1,4-dihydrobenzofuro[3,2-b]pyridines could be aromatized in the presence of DBU to afford benzofuro[3,2-b]pyridines

  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。
• Asymmetric Organocatalysis in the Synthesis of Pyrrolidine Derivatives­ Bearing a Benzofuran-3(2H)-one Scaffold
  作者：Łukasz Albrecht、Dorota Kowalczyk、Jakub Wojciechowski

  DOI：10.1055/s-0035-1562483

  日期：——

  The approach, based on the [3+2] cycloaddition between 2-arylidenebenzofuran-3(2H)-ones and imines derived from salicylaldehyde and diethyl aminomalonates, benefits from broad substrate scope, high chemical and stereochemical efficiency, and operational simplicity. Notably, simple and readily available quinine is employed as the catalyst of the reaction. Target products bearing two biologically relevant

  摘要 报道了一种新的对映体和非对映体选择性方法，该方法对带有苯并呋喃-3（2 H）-一个支架的吡咯烷衍生物。该方法基于2-亚芳基苯并呋喃-3（2 H）-与水杨醛和氨基丙二酸二乙酯衍生的亚胺之间的[3 + 2]环加成反应，该方法得益于广泛的底物范围，较高的化学和立体化学效率以及操作简便性。值得注意的是，采用简单易得的奎宁作为反应的催化剂。已经以优异的产率和高度立体选择性的方式获得了具有两个生物学上相关的杂环部分和三个相邻的立体异构中心（其中一个是四级的）的目标产物。 报道了一种新的对映体和非对映体选择性方法，该方法对带有苯并呋喃-3（2 H）-一个支架的吡咯烷衍生物。该方法基于2-亚芳基苯并呋喃-3（2 H）-与水杨醛和氨基丙二酸二乙酯衍生的亚胺之间的[3 + 2]环加成反应，该方法得益于广泛的底物范围，较高的化学和立体化学效率以及操作简便性。值得注意的是，采用简单易得的奎宁作为反应的催化剂