dimethyl 2-(1-benzofuran-2-ylmethyl)malonate

• 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: dimethyl 2-(1-benzofuran-2-ylmethyl)malonate
• 英文别名: dimethyl 2-(2-benzofurylmethyl)propanedioate；Dimethyl 2-(1-benzofuran-2-ylmethyl)propanedioate
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: ZRZFCMBDNOHGGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-碘-2-(甲氧基甲氧基)苯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 platinum(II) chloride 作用下， 以 四氢呋喃 、 异丙醇 、 甲苯 为溶剂， 反应 1.0h， 生成 dimethyl 2-(1-benzofuran-2-ylmethyl)malonate
  参考文献：
  名称：

  通过 PtCl2 催化的炔烃分子内碳烷氧基化或碳胺化的杂环

  摘要：

  PtCl2 是炔烃分子内加氢烷氧基化、碳烷氧基化、加氢胺化和氨基化反应的方便催化剂，分别影响取代的苯并[b]呋喃、吲哚-和异色烯-1-酮衍生物的形成。此过程允许（取代的）烯丙基、甲氧基甲基 (MOM)、苄氧基甲基 (BOM) 和（三甲基甲硅烷基）乙氧基甲基 (SEM) 基团从氧转移到碳，并且与易于氧化插入低价的官能团相容以前用于类似目的的金属种类。尽管某些反应甚至可以在空气中进行，但在 CO 气氛下进行时反应速率会显着增加。 提出了一个机械原理，

  DOI：

  10.1021/ja055659p

文献信息

• Palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-, benzothiophene- and indole-based substrates by dimethyl malonate anion
  作者：Gaëlle Primault、Jean-Yves Legros、Jean-Claude Fiaud

  DOI：10.1016/s0022-328x(03)00728-9

  日期：2003.12

  The palladium-catalyzed benzylic-like nucleophilic substitution of acetates derived from benzofuran, benzothiophene and indole was investigated. The asymmetric substitution on racemic 1-(2-benzofuryl)ethyl acetate gave disappointing results, but the substitution product was obtained in 98% ee from (S)-1-(2-benzofuryl)ethyl acetate with overall retention of configuration.

  研究了钯催化的衍生自苯并呋喃，苯并噻吩和吲哚的乙酸酯的苄基样亲核取代。外消旋的1-（2-苯并呋喃基）乙酸乙酯的不对称取代反应令人失望，但取代产物是由（S）-1-（2-苯并呋喃基）乙酸乙酯以98％ee的形式得到的，且保留了构型。
• A new structural alternative in benzo[b]furans for antimicrobial activity
  作者：M. Wahab Khan、M. Jahangir Alam、M.A. Rashid、R. Chowdhury

  DOI：10.1016/j.bmc.2005.05.009

  日期：2005.8

  Two series of 2-substituted and three new diacetyl benzofurans were synthesized through palladium-catalyzed reactions, and their in vitro antimicrobial spectra were assessed. The compounds demonstrated mild to significant growth inhibition against antibiotic-susceptible standard and clinically isolated strains of Gram-positive and Gram-negative bacteria as well as human fungal pathogens. Ampicillin and kanamycin were used as references for antibacterial screening; nystatin and amphotericin B were used for antifungal screening. Varying substitution at the benzofuran moiety and subsequent antimicrobial screening identified the C-3-acetyl functionality as a new structural alternative for optimal antimicrobial property in the benzofuran class of Compounds. (c) 2005 Elsevier Ltd. All rights reserved.