methyl 2-(4-methoxycarbonylphenyl)-5-methylbenzoate | 1382034-03-8

• 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: methyl 2-(4-methoxycarbonylphenyl)-5-methylbenzoate
• CAS: 1382034-03-8
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: FZQUYCYNHQKSDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-methoxycarbonylphenyl)-5-methylbenzoate 在 N-乙酰-L-丙氨酸 、 palladium diacetate 、 silver carbonate 、 对苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 2'-(3-methoxy-3-oxoprop-1-en-1-yl)-4'-(methoxycarbonyl)-4-methyl-[1,1'-biphenyl]-2-carboxylicacid
  参考文献：
  名称：

  Remote and Selective C(sp²)–H Olefination for Sequential Regioselective Linkage of Phenanthrenes

  摘要：

  Biphenylcarboxylic acid with two competing C(sp(2))-H sites was designed for site selective C(sp(2))-H functionalization by developing carboxylic acids assisted remote and selective olefination via 7-membered palladacycle. Mechanism investigation and DFT calculations reveal a kinetics-determined process, which could be utilized to explore a variety of remote site selectivity. The practicability of this method was highlighted by the precise construction of phenathrene under sequential site selectivity.

  DOI：

  10.1021/acs.orglett.0c01208
• 作为产物：
  描述：

  4-甲氧羰基苯硼酸 、 2-溴-5-甲基苯甲酸甲酯 在 四(三苯基膦)钯 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到methyl 2-(4-methoxycarbonylphenyl)-5-methylbenzoate
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Glutamate Carboxypeptidase II (GCPII) Inhibitors Based on Thioalkylbenzoic Acid Scaffolds

  摘要：

  A series of thiol-based glutamate carboxypeptidase II (GCPII) inhibitors have been synthesized with either a 3-(mercaptomethyl)benzoic acid or 2-(2-mercaptoethyl)benzoic acid scaffold. Potent inhibitors were identified from each of the two scaffolds with IC50 values in the single-digit nanomolar range, including 2-(3-carboxybenzyloxy)-5-(mercaptomethyl)benzoic acid 27c and 3-(2-mercaptoethyl)-biphenyl-2,3'-dicarboxylic acid 35c. Compound 35c was found to be metabolically stable and selective over a number of targets related to glutamate-mediated neurotransmission. Furthermore, compound 35c was found to be orally available in rats and exhibited efficacy in an animal model of neuropathic pain following oral administration.

  DOI：

  10.1021/jm300488m