3-ethynyl-4-hydroxybenzonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-ethynyl-4-hydroxybenzonitrile
• 化学式: C₉H₅NO
• 分子量: 143.145
• InChiKey: AKVFWVJULJRERP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethynyl-4-hydroxybenzonitrile 在 二(三苯基膦)环戊二烯基氯化钌(II) 作用下， 以 吡啶 为溶剂， 反应 1.0h， 以54%的产率得到1-苯并呋喃-5-甲腈
  参考文献：
  名称：

  通过催化Ru Vinylidenesnes环芳香异构和双同炔丙基醇的形成：苯并呋喃和异色酮的形成

  摘要：

  钌催化的芳香族均丙和双均丙炔醇的环异构化可有效提供苯并呋喃和异苯并二氢萘。这些（5-和6-过程被证明是化疗和区域选择性内切环化）从关键孺偏二中间体衍生的。胺/铵碱式酸对的存在对于催化循环至关重要。

  DOI：

  10.1021/ol902212h
• 作为产物：
  描述：

  2-溴-4-氰基苯基乙酸酯 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 3-ethynyl-4-hydroxybenzonitrile
  参考文献：
  名称：

  [EN] ANTIBACTERIAL AND ANTIFUNGAL PLEUROMUTILIN CONJUGATES
  [FR] CONJUGUÉS DE PLEUROMUTILINE ANTIBACTÉRIENS ET ANTIFONGIQUES

  摘要：

  提供了具有三唑基侧链的含有蓝藻蛋白酮骨架的化合物（1）的公式。这些化合物可用于治疗细菌感染和真菌感染。重要的是，可以有效治疗由多药耐药细菌引起的感染，如耐甲氧西林金黄色葡萄球菌（MRSA）引起的感染。

  公开号：

  WO2021219813A1

文献信息

• Palladium-Catalyzed Reaction of <i>o</i>-Ethynylphenols, <i>o</i>-((Trimethylsilyl)ethynyl)phenyl Acetates, and <i>o</i>-Alkynylphenols with Unsaturated Triflates or Halides:  A Route to 2-Substituted-, 2,3-Disubstituted-, and 2-Substituted-3-acylbenzo[<i>b</i>]furans
  作者：Antonio Arcadi、Sandro Cacchi、Mario Del Rosario、Giancarlo Fabrizi、Fabio Marinelli

  DOI：10.1021/jo961051a

  日期：1996.1.1

  The reaction of o-ethynylphenols 3 with a wide variety of unsaturated halides or triflates 6 in the presence of Pd(OAc)(2)(PPh(3))(2), CuI, and Et(3)N (procedure A) gives 2-vinyl- and 2-arylbenzo[b]furans 7, in good to high yield, through a palladium-catalyzed coupling followed by an in situ cyclization step. Small amounts of 2,3-disubstituted-benzo[b]furans 8 are usually isolated as side products. In some cases, however, compounds 8 are generated in significant yield or even as the main products. The formation of 8 can be prevented by employing alternative procedures (B and C) that use o-((trimethylsilyl)ethynyl)phenyl acetates 5 as starting building blocks. Procedure B is based on the palladium-catalyzed reaction of 5 with 6 in the presence of Pd(PPh(3))(4), Et(3)N, and n-Bu(4)NF, followed by the hydrolysis of the resultant coupling derivative 12 under basic conditions. Procedure C affords 7 through an in situ coupling/cyclization of 5 with 6 in the presence of Pd(PPh(3))(4) and KOBu(t). The utilization of o-alkynylphenols 9 as the starting alkynes in the palladium-catalyzed reaction with 6 leads to the formation of 2,3-disubstituted-benzo[b]furans 13 through an annulation process promoted by sigma-vinyl- and sigma-arylpalladium complexes generated in situ. The best results in this case are obtained by using KOAc and Pd(PPh(3))(4). In the presence of KOAc and Pd(PPh(3))(4), and under an atmosphere of carbon monoxide, the reaction of o-alkynylphenols with 6 provides 2-vinyl- and 2-aryl-3-acylbenzo[b]furans 14.