N-(3-(4-fluorophenylamino)-1,1-bis(methylthio)-3-oxoprop-1-en-2-yl)benzamide | 1236209-14-5

• 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: N-(3-(4-fluorophenylamino)-1,1-bis(methylthio)-3-oxoprop-1-en-2-yl)benzamide
• 英文别名: N-[3-(4-fluoroanilino)-1,1-bis(methylsulfanyl)-3-oxoprop-1-en-2-yl]benzamide
• CAS: 1236209-14-5
• 化学式: C₁₈H₁₇FN₂O₂S₂
• 分子量: 376.476
• InChiKey: PWRDLFIAWZQKOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-(4-fluorophenylamino)-1,1-bis(methylthio)-3-oxoprop-1-en-2-yl)benzamide 在 silver carbonate 作用下， 以 乙腈 为溶剂， 以74%的产率得到N-(4-fluorophenyl)-5-(methylthio)-2-phenyloxazole-4-carboxamide
  参考文献：
  名称：

  4-Bis(methylthio)methylene-2-phenyloxazol-5-one: Versatile Template for Synthesis of 2-Phenyl-4,5-functionalized Oxazoles

  摘要：

  4-Bis(methylthio)methylene-2-phenyloxazol-5-one has been shown to be a versatile template for the synthesis of various 2-phenyl-3,4-substituted oxazoles via nucleophilic ring-opening of oxazolone with various oxygen, nitrogen, and carbon nucleophiles and subsequent 5-endo cyclization of the resulting acyclic adducts in the presence of silver carbonate.

  DOI：

  10.1021/jo100941f
• 作为产物：
  描述：

  4-(Bis-methylmercaptomethylen)-2-phenyl-2-oxazolin-5-on 、 4-氟苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以78%的产率得到N-(3-(4-fluorophenylamino)-1,1-bis(methylthio)-3-oxoprop-1-en-2-yl)benzamide
  参考文献：
  名称：

  4-Bis(methylthio)methylene-2-phenyloxazol-5-one: Versatile Template for Synthesis of 2-Phenyl-4,5-functionalized Oxazoles

  摘要：

  4-Bis(methylthio)methylene-2-phenyloxazol-5-one has been shown to be a versatile template for the synthesis of various 2-phenyl-3,4-substituted oxazoles via nucleophilic ring-opening of oxazolone with various oxygen, nitrogen, and carbon nucleophiles and subsequent 5-endo cyclization of the resulting acyclic adducts in the presence of silver carbonate.

  DOI：

  10.1021/jo100941f

文献信息

• 4-Bis(methylthio)methylene-2-phenyloxazol-5-one: Versatile Template for Synthesis of 2-Phenyl-4,5-functionalized Oxazoles
  作者：Nimesh C. Misra、H. Ila

  DOI：10.1021/jo100941f

  日期：2010.8.6

  4-Bis(methylthio)methylene-2-phenyloxazol-5-one has been shown to be a versatile template for the synthesis of various 2-phenyl-3,4-substituted oxazoles via nucleophilic ring-opening of oxazolone with various oxygen, nitrogen, and carbon nucleophiles and subsequent 5-endo cyclization of the resulting acyclic adducts in the presence of silver carbonate.
• 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.