2-(5-Methylfuran-2-yl)-2-(5-methyl-4-phenylthiazol-2-yl)propane

• 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-(5-Methylfuran-2-yl)-2-(5-methyl-4-phenylthiazol-2-yl)propane
• 英文别名: 5-Methyl-2-[2-(5-methylfuran-2-yl)propan-2-yl]-4-phenyl-1,3-thiazole
• 化学式: C₁₈H₁₉NOS
• 分子量: 297.421
• InChiKey: NXLNVWVNSWSSFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基呋喃 、 2-(Benzotriazol-1-yl)-2-(5-methyl-4-phenylthiazol-2-yl)propane 在 zinc dibromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以59%的产率得到2-(5-Methylfuran-2-yl)-2-(5-methyl-4-phenylthiazol-2-yl)propane
  参考文献：
  名称：

  1-(Cyanomethyl)benzotriazole as a Convenient Precursor for the Synthesis of 2-Substituted Thiazoles

  摘要：

  Treatment of 1-(cyanomethyl)benzotriazole with hydrogen peroxide followed by a Lawesson reagent afforded by a Lawesson reagent afforded (benzotriazol-1-yl)thioacetamide which condensed with alpha-halo carbonyl compounds (Hantzsch thiazole synthesis) to give the corresponding 2-(benzotriazol-1-ylmethyl)thiazoles. Lithiation of 2-(benzotriazol-1-ylmethyl)-4-phenylthiazole with butyllithium occurred exclusively at the methylene group, and subsequent quenching of the resulting anion with alkyl halides produced the corresponding alkylated products in good yields. Treatment of these intermediates with Grignard reagents in toluene or with electron-rich heterocycles in the presence of zinc bromide resulted in the displacement of benzotriazole to afford the corresponding thiazoles with elaborated 2-substituents.

  DOI：

  10.1021/jo00122a053