3-(4-methoxybenzylidene)benzofuran-2(3H)-one | 59020-03-0

• 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: 3-(4-methoxybenzylidene)benzofuran-2(3H)-one
• 英文别名: (Z)-3-(4-methoxybenzylidene)benzofuran-2(3H)-one；3-(4-methoxy-benzylidene)-3H-benzofuran-2-one；3-(4-Methoxy-benzyliden)-3H-benzofuran-2-on；(3Z)-3-[(4-methoxyphenyl)methylidene]-1-benzofuran-2-one
• CAS: 59020-03-0
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: RKEZZKHXWBKFKY-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：

  3-(4-methoxybenzylidene)benzofuran-2(3H)-one 在 盐酸 、 三乙胺 作用下， 以 苯 为溶剂， 反应 27.0h， 生成 (4'SR;5'RS) ethyl 4-(4-methoxyphenyl)-5-(orthohydroxyphenyl)-3-phenyl-4,5-dihydroisoxazoline-5-carboxylate
  参考文献：
  名称：

  Spiroheterocycles from the Reaction of Arylnitrile Oxides with Some (Z)-3-Arylidene-2(3H)-benzofuranones. New Access to Orthohydroxyphenylisoxazoline Esters

  摘要：

  DOI：

  10.3987/com-06-10918
• 作为产物：
  描述：

  2-(2-hydroxy-phenyl)-3-(4-methoxy-phenyl)-acrylic acid 生成 3-(4-methoxybenzylidene)benzofuran-2(3H)-one
  参考文献：
  名称：

  Czaplicki; v. Kostanecki; Lampe, Chemische Berichte, 1909, vol. 42, p. 834

  摘要：

  DOI：

文献信息

• Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity
  作者：Rajkumar Lalji Sahani、Manoj D. Patil、Sachin Bhausaheb Wagh、Rai-Shung Liu

  DOI：10.1002/anie.201806883

  日期：2018.11.5

  The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile‐directed chemoselectivity through cooperative catalysis. For 1‐alkyn‐4‐ols and 2‐ethynylphenols, their gold‐catalyzed nitrone oxidations afforded N‐containing dihydrofuran‐3(2H)‐ones with syn selectivity. The mechanism involves the Mannich reactions of gold

  描述了由炔烃，硝酮和亲核试剂催化形成烯醇金的过程，它们的曼尼希反应通过协同催化导致亲核试剂导向的化学选择性。1-炔-4-醇及2- ethynylphenols，得到含有N-二氢呋喃-3-（2-他们的黄金-催化的硝酮氧化ħ） -酮与顺式 选择性。该机制涉及通过O-H-N氢键基序的金烯酸酯与亚胺的曼尼希反应。对于芳氧基乙炔来说，它们的金烯醇盐会与硝酮选择性反应，生成受C-H-O氢键控制的3-亚烷基苯并呋喃-2-酮。
• Synthesis of New Spirocyclopropane and Oxadiazole Products
  作者：Amel Haouas、Naoufel Ben Hamadi[]、Moncef Msaddek

  DOI：10.1002/jhet.2249

  日期：2015.11

  In explorations of synthesis and chemistry of spiroheterocycles, we found that the reaction of 2‐diazopropane with arylidene‐benzofuran‐2(3H)‐one and arylidene‐benzofuran‐3(2H)‐one derivatives generated the spirocyclopropane products. In addition to the expected cycloadducts, an unexpected oxadiazole was formed in some cases. The structures of the obtained adducts have been assigned by means of spectroscopic

  在螺环杂环化合物的合成和化学研究中，我们发现2-重氮丙烷与亚芳基-苯并呋喃-2（3 H）-one和亚芳基-苯并呋喃-3（2 H）-one衍生物的反应生成了螺环丙烷产物。除预期的环加合物外，在某些情况下还会生成意外的恶二唑。所获得的加合物的结构已经通过光谱方法进行了分配。
• Enantioselective construction of spiro-tetrahydroquinoline scaffolds through asymmetric catalytic cascade reactions
  作者：Jia-Lu Zhang、Rui Ma、Huan-Huan Zhao、Peng-Fei Xu

  DOI：10.1039/d2cc00502f

  日期：——

  asymmetric catalytic cascade reactions catalyzed by quinine-derived chiral bifunctional squaramide organocatalysts. In this approach, differently substituted spiro-tetrahydroquinoline derivatives were smoothly obtained with high yields, and excellent diastereoselectivities and enantioselectivities (up to 99% yield, up to >20 : 1 dr, up to >99% ee, 40 examples) under mild reaction conditions.

  通过由奎宁衍生的手性双功能方酰胺有机催化剂催化的不对称催化级联反应，成功地开发了一种有效而简洁的策略，用于将螺四氢喹啉与螺苯并呋喃酮合并成一个新的骨架。在这种方法中，不同取代的螺四氢喹啉衍生物以高产率顺利获得，在温和反应下具有优异的非对映选择性和对映选择性（高达 99% 产率，高达 >20 : 1 dr，高达 >99% ee，40 个实例）状况。
• Design of novel dispirooxindolopyrrolidine and dispirooxindolopyrrolothiazole derivatives as potential antitubercular agents
  作者：Chourouk Mhiri、Sarra Boudriga、Moheddine Askri、Michael Knorr、Dharmarajan Sriram、Perumal Yogeeswari、Frédéric Nana、Christopher Golz、Carsten Strohmann

  DOI：10.1016/j.bmcl.2015.07.069

  日期：2015.10

  With the aim to develop new potent antitubercular agents, a series of novel dispirooxindolopyrrolidines and dispirooxindolopyrrolothiazoles have been synthesized via a three-component 1,3-dipolar cycloaddition of (Z)-3-arylidenebenzofuran-2-ones, substituted isatin derivatives and alpha-aminoacids. The stereochemistry of the spiroadducts has been confirmed by an X-ray diffraction analysis. All the target heterocycles were evaluated for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strain and the most active compounds were subjected to cytotoxicity studies against (RAW 264.7) cell lines. Among them, twelve compounds showed potent anti-tubercular activity with MIC ranging from 1.56 to 6.25 mu g/mL. In particular dispirooxindolopyrrolothiazole derivatives 5c and 5f were found to be the most active (MIC of 1.56 mu g/mL) with a good safety profile (27.53% and 20.74% at 50 mu M, respectively). This is the first report demonstrating the benzofuranone oxindole hybrids as potential antimycobacterial agents. (C) 2015 Elsevier Ltd. All rights reserved.
• Msaddek, Moncef; Rammah, Mohamed; Ciamala, Kabula, Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 12, p. 825 - 832
  作者：Msaddek, Moncef、Rammah, Mohamed、Ciamala, Kabula、Vebrel, Joel、Laude, Bernard

  DOI：——

  日期：——