ethyl 5-(1-methyl-1H-pyrrol-2-yl)-2-phenylthiazole-4-carboxylate | 1446782-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-(1-methyl-1H-pyrrol-2-yl)-2-phenylthiazole-4-carboxylate
• 英文别名: Ethyl 5-(1-methylpyrrol-2-yl)-2-phenyl-1,3-thiazole-4-carboxylate；ethyl 5-(1-methylpyrrol-2-yl)-2-phenyl-1,3-thiazole-4-carboxylate
• CAS: 1446782-19-9
• 化学式: C₁₇H₁₆N₂O₂S
• 分子量: 312.392
• InChiKey: CCSABYZCYZBODM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-[(1-methyl-1H-pyrrol-2-yl)(methylthio)methylene]-2-phenyloxazol-5(4H)-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 ethyl 5-(1-methyl-1H-pyrrol-2-yl)-2-phenylthiazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson’s Reagent-Mediated Chemoselective Thionation–Cyclization of Functionalized Enamides

  摘要：

  An efficient route to 2-phenyl/(2-thienyl)-5-(het)aryl/(methylthio)-4-functionalized thiazoles via one-step chemoselective thionation-cyclization of highly functionalized enamides mediated by Lawesson's reagent is reported. These enamide precursors are obtained by nucleophilic ring-opening of 2-phenyl/(2-thienyl)-4-[bis(methylthio)/(methylthio)(het)arylmethylene]-5-oxazolones with alkoxides and a variety of primary aromatic/aliphatic amines or amino acid esters, leading to the introduction of an ester, an N-substituted carboxamide, or a peptide functionality in the 4-position of the product thiazoles.

  DOI：

  10.1021/jo401208u

文献信息

• Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson’s Reagent-Mediated Chemoselective Thionation–Cyclization of Functionalized Enamides
  作者：S. Vijay Kumar、G. Parameshwarappa、H. Ila

  DOI：10.1021/jo401208u

  日期：2013.7.19

  An efficient route to 2-phenyl/(2-thienyl)-5-(het)aryl/(methylthio)-4-functionalized thiazoles via one-step chemoselective thionation-cyclization of highly functionalized enamides mediated by Lawesson's reagent is reported. These enamide precursors are obtained by nucleophilic ring-opening of 2-phenyl/(2-thienyl)-4-[bis(methylthio)/(methylthio)(het)arylmethylene]-5-oxazolones with alkoxides and a variety of primary aromatic/aliphatic amines or amino acid esters, leading to the introduction of an ester, an N-substituted carboxamide, or a peptide functionality in the 4-position of the product thiazoles.