methyl 4-chloro-5-(2-(1-imidazolyl)-ethoxy)-thiophene-2-carboxylate | 91505-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 4-chloro-5-(2-(1-imidazolyl)-ethoxy)-thiophene-2-carboxylate
• 英文别名: 4-Chloro-5-[2-(1-imidazolyl)-1-ethoxy]-thiophene-2-carboxylic acid methyl ester；methyl 4-chloro-5-(2-imidazol-1-ylethoxy)thiophene-2-carboxylate
• CAS: 91505-17-8
• 化学式: C₁₁H₁₁ClN₂O₃S
• 分子量: 286.739
• InChiKey: ROMGTBCMOLKESS-UHFFFAOYSA-N

物化性质

• 沸点：
  494.4±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-chloro-5-(2-(1-imidazolyl)-ethoxy)-thiophene-2-carboxylate 生成 5-(2-(1-咪唑基)乙氧基)-4-氯噻吩-2-羧酸
  参考文献：
  名称：

  BINDER, D.;NOE, C.

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯-2-酰氯噻吩 在 吡啶 、 咪唑 、 盐酸 、 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 17.42h， 生成 methyl 4-chloro-5-(2-(1-imidazolyl)-ethoxy)-thiophene-2-carboxylate
  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

• Derivatives of thiophene-2-carboxylic acid and their pharmaceutically
  申请人：Laevosan-Gesellschaft m.b.H. & Co. KG

  公开号：US04590203A1

  公开（公告）日：1986-05-20

  The disclosure is directed to new derivatives of thiophene-2-carboxylic acid and the pharmaceutically acceptable acid or base addition salts thereof as well as to the process for the preparation thereof. The compounds of the invention have the structural formula ##STR1## in which R in position 3 or 4 of the thiophene nucleus is hydrogen, methyl, chlorine or bromine and R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl. The compounds have a remarkably strong inhibitory effect on the thromboxane synthetase and are useful for the treatment of conditions such as inflammation, hypertension, thrombus, apoplexy, asthma, angina pectoris, ischemic heart diseases, ischemic conditions, migraine and vascular complications in connection with diabetes.

  本公开涉及噻吩-2-羧酸的新衍生物及其药学上可接受的酸或碱盐的制备方法。本发明的化合物具有结构式##STR1##其中，噻吩核的3或4号位的R为氢、甲基、氯或溴，R.sub.1为氢或C.sub.1-C.sub.4烷基。这些化合物具有显著的凝血酶合成酶抑制作用，并可用于治疗炎症、高血压、血栓、中风、哮喘、心绞痛、缺血性心脏病、缺血性病症、偏头痛和与糖尿病相关的血管并发症等疾病。
• BINDER, D.;NOE, C.
  作者：BINDER, D.、NOE, C.

  DOI：——

  日期：——
• US4590203A
  申请人：——

  公开号：US4590203A

  公开（公告）日：1986-05-20
• 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.