2-Phenyl-oxazol-4,5-dicarbonsaeure | 15926-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Phenyl-oxazol-4,5-dicarbonsaeure
• 英文别名: 2-Phenyl-1,3-oxazole-4,5-dicarboxylic acid
• CAS: 15926-44-0
• 化学式: C₁₁H₇NO₅
• 分子量: 233.18
• InChiKey: YRGAADYUKSMBJS-UHFFFAOYSA-N

物化性质

• 熔点：
  215 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  506.0±60.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dimethyl 2-phenyloxazole-4,5-dicarboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以93%的产率得到2-Phenyl-oxazol-4,5-dicarbonsaeure
  参考文献：
  名称：

  A Rational Approach to the Design of Selective Substrates and Potent Nontransportable Inhibitors of the Excitatory Amino Acid Transporter EAAC1 (EAAT3). New Glutamate and Aspartate Analogues as Potential Neuroprotective Agents

  摘要：

  Two three-dimensional receptor interaction models for EAAT substrates and nontransportable inhibitors have been developed, and new glutamate (Glu) and aspartate (Asp) analogues have been synthesized. The analogues la and 3 represent novel lead compounds for the development of EAAT substrates and nontransportable inhibitors, selective for EAATs over iGluRs, as possible neuroprotective agents useful to minimize the progression of chronic or acute neurodegenerative diseases, The role played by the protonatable amine function in the interaction with EAATs has been discussed.

  DOI：

  10.1021/jm015509z

文献信息

• Studies on Seven-membered Ring Compounds. XXIII. Reactions of Tropylium Ions Having Fused Heterocyclic System with Various Amines
  作者：Nobuo Soma、Jun-ichi Nakazawa、Taiichiro Watanabe、Yoshio Sato、Genshun Sunagawa

  DOI：10.1248/cpb.15.627

  日期：——

  Reactions of tropylium ions having a fused heterocyclic system with various amines were examined. Reaction of 2-phenyloxazolotropylium monomethylsulfate (I) and 2-phenylthiazotropylium chloride (XXIV) with dimethylamine produced 2-phenyl-6-dimethylamino-6H-cycloheptoxazole (II) and 6-dimethylamino-2-phenyl-6H-cycloheptathiazole (XXV), respectively. Regarding the reaction with p-toluidine, both I and 1-p-tolyl-2-phenylimidazolotropylium chloride (XXVI) gave 1-p-tolyl-2-phenyl-1, 6-dihydrocycloheptimidazole (VI) and 1-p-tolyl-2-phenyl-6-p-tolylimino-1, 6-dihydrocycloheptimidazole (VII). Reaction of I with N-methylaniline produced 2-phenyl-6-p-methylaminophenyl-6H-cycloheptoxazole (XIX) and 2-phenyl-4-p-methylaminophenyl-4H-cycloheptoxazole (XX). From these results, it is concluded that the tropylium ions condensing a heterocycle has a priority for amination at C-6.

  研究了具有融合杂环体系的托品鎓离子与各种胺的反应。2- 苯并恶唑丙基鎓一甲基硫酸盐（I）和 2- 苯并噻唑丙基鎓氯化物（XXIV）与二甲胺反应，分别生成了 2-苯基-6-二甲氨基-6H-环庚恶唑（II）和 6-二甲氨基-2-苯基-6H-环庚硫唑（XXV）。至于与对甲苯胺的反应，I 和 1-对甲苯基-2-苯基咪唑基氯化铵（XXVI）都得到了 1-对甲苯基-2-苯基-1，6-二氢环庚基咪唑（VI）和 1-对甲苯基-2-苯基-6-对甲苯基咪唑基-1，6-二氢环庚基咪唑（VII）。I 与 N-甲基苯胺反应生成了 2-苯基-6-对甲氨基苯基-6H-环庚恶唑（XIX）和 2-苯基-4-对甲氨基苯基-4H-环庚恶唑（XX）。从这些结果中可以得出结论，托品鎓离子缩合杂环时优先在 C-6 处进行胺化。