4-chloro-5-(2-(1-imidazolyl)-ethoxy)-thiophene-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-chloro-5-(2-(1-imidazolyl)-ethoxy)-thiophene-2-carboxylic acid
• 英文别名: 4-Chloro-5-(2-imidazol-1-ylethoxy)thiophene-2-carboxylic acid
• 化学式: C₁₀H₉ClN₂O₃S
• 分子量: 272.712
• InChiKey: CFFCMPFFYZXIKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氯-2-酰氯噻吩 在 吡啶 、 咪唑 、 盐酸 、 sodium hydroxide 、 氯化亚砜 、 磺酰氯 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.42h， 生成 4-chloro-5-(2-(1-imidazolyl)-ethoxy)-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Substituted Alkoxythiophenes: Thiophene Analogues of Dazoxiben

  摘要：

  The synthesis of the thiophene analogue of dazoxiben - one of the most selective TXA(2)-synthase inhibitors - and its derivatization to a chlorinated, more lipophilic product is described. The ethylenoxy moiety was introduced via nucleophilic aromatic substitution of halogenated thiophene carboxylic esters, the imidazol residue, by use of a t-butoxy group as a synthon after ether cleavage and halogenation. Also, at this step chlorination of the thiophene moiety was carried out. After ester hydrolysis the target compounds were obtained as hydrochlorides.

  DOI：

  10.1007/pl00010245

文献信息

• Thiophen-2-carbonsäurederivate und Verfahren zu deren Herstellung
  申请人：Laevosan-Gesellschaft m.b.H.

  公开号：EP0109381B1

  公开（公告）日：1986-07-30
• Synthesis of Substituted Alkoxythiophenes: Thiophene Analogues of Dazoxiben
  作者：Dieter Binder、Michael Pyerin、Friedrich Pusterer

  DOI：10.1007/pl00010245

  日期：1999.5

  The synthesis of the thiophene analogue of dazoxiben - one of the most selective TXA(2)-synthase inhibitors - and its derivatization to a chlorinated, more lipophilic product is described. The ethylenoxy moiety was introduced via nucleophilic aromatic substitution of halogenated thiophene carboxylic esters, the imidazol residue, by use of a t-butoxy group as a synthon after ether cleavage and halogenation. Also, at this step chlorination of the thiophene moiety was carried out. After ester hydrolysis the target compounds were obtained as hydrochlorides.