5-p-Tolyl-thiophene-3-carboxylic acid methyl ester | 130655-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-p-Tolyl-thiophene-3-carboxylic acid methyl ester
• 英文别名: methyl 5-(4-methylphenyl)thiophene-3-carboxylate
• CAS: 130655-92-4
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: MZOFEPQRUDFSKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  357.1±30.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-p-Tolyl-thiophene-3-carboxylic acid methyl ester 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 2.5h， 生成 2-(5-p-Tolyl-thiophen-3-ylmethyl)-malonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009
• 作为产物：
  描述：

  3-噻吩甲酸甲酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 sodium carbonate 、 三(邻甲基苯基)磷 、 4,4'-二叔丁基-2,2'-二吡啶 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成 5-p-Tolyl-thiophene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates

  摘要：

  A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.

  DOI：

  10.1021/ol301570t

文献信息

• 取代噻吩类化合物、其制备方法及其用途
  申请人：中国科学院上海药物研究所

  公开号：CN112142711B

  公开（公告）日：2022-03-29

  本发明涉及一种通式I表示的噻吩类化合物及其药学上可用的盐、其制备方法、包含其的药物组合物及其用途。所述噻吩类化合物及其药学上可用的盐作为一种新型雌激素相关受体α(ERRα)反向激动剂。这些化合物能用来治疗与ERR和ERRα相关的疾病，如癌症、骨质疏松、糖尿病、抗衰老、减肥等。经过进一步的优化和筛选后，有望研发成为新型的预防及治疗肿瘤或其他ERRα相关疾病的药物。