(E)-3-(4-Azido-2-phenyl-thiazol-5-yl)-acrylic acid ethyl ester | 193959-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-3-(4-Azido-2-phenyl-thiazol-5-yl)-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-(4-azido-2-phenyl-1,3-thiazol-5-yl)prop-2-enoate
• CAS: 193959-10-3
• 化学式: C₁₄H₁₂N₄O₂S
• 分子量: 300.341
• InChiKey: QFEMLMFVVNVYEP-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-azido-5-formyl-2-phenylthiazole 在 氢氧化钾 、 sodium azide 、 sodium nitrite 作用下， 以 四氢呋喃 、 三氟乙酸 为溶剂， 反应 6.5h， 生成 (E)-3-(4-Azido-2-phenyl-thiazol-5-yl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Neighbouring group effects on rates of thermolysis of 4-azidothiazoles

  摘要：

  Rate measurements for thermolysis of 4-azidothiazoles in p-xylene solution have identified neighbouring group effects from nitro (19-fold rate increase), phenyliminomethyl (16), formyl (4.5) and acetyl (2.2) substituents in the 5-position. These effects are very similar in magnitude to those measured for 3-azidothiophenes, whereas in azidobenzenes the rate increases are much larger, 5-Substituents in 4-azidothiazole which are capable of conjugative donation (phenyl, ethyl propenoate) also increased the reaction rate. The reactions involving neighbouring group participation led to cyclized products from the 4-azidothiazoles though not all of these products were stable under the thermolysis conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00638-8