5-fluoro-4-phenyl-2-propargylthiothiazole | 493046-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-fluoro-4-phenyl-2-propargylthiothiazole
• 英文别名: 5-Fluoro-4-phenyl-2-prop-2-ynylsulfanyl-1,3-thiazole
• CAS: 493046-74-5
• 化学式: C₁₂H₈FNS₂
• 分子量: 249.333
• InChiKey: WZKNZFNSODLJHC-UHFFFAOYSA-N

物化性质

• 沸点：
  370.4±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-4-phenyl-2-propargylthiothiazole 在 triethylamine pentahydrogen fluoride salt 作用下， 以 乙二醇二甲醚 为溶剂， 以60%的产率得到4-phenyl-2-propargylthio-2,5,5-trifluoro-2,5-dihydrothiazole
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 64.¹ Anodic Mono- and Difluorination of Thiazolyl Sulfides

  摘要：

  The anodic fluorination of 2-thiazolyl methyl sulfide, 2-thiazolyl propargyl sulfide, and 2-thiazolyl acetonyl sulfide was successfully carried out to provide the corresponding 5-fluorothiazole and 2,5,5-trifluorothiazoline derivatives. The latter products were readily hydrolyzed to give isolable 5,5-difluoro-2-hydroxythiazoline derivatives. On the other hand, anodic fluorination of 2-thiazolyl cyanomethyl sulfide afforded 5-fluorothiazole and a-fluorinated thiazole derivatives. Thus, the product selectivity was found to be greatly changed by the electron-withdrawing ability of substituents at the side chain of the thiazole ring. This is the first report of a successful anodic fluorination of a thiazole ring.

  DOI：

  10.1021/jo020411t
• 作为产物：
  描述：

  2-巯基-4-苯基噻唑 在 triethylamine pentahydrogen fluoride salt 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 10.0h， 生成 5-fluoro-4-phenyl-2-propargylthiothiazole
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 64.¹ Anodic Mono- and Difluorination of Thiazolyl Sulfides

  摘要：

  The anodic fluorination of 2-thiazolyl methyl sulfide, 2-thiazolyl propargyl sulfide, and 2-thiazolyl acetonyl sulfide was successfully carried out to provide the corresponding 5-fluorothiazole and 2,5,5-trifluorothiazoline derivatives. The latter products were readily hydrolyzed to give isolable 5,5-difluoro-2-hydroxythiazoline derivatives. On the other hand, anodic fluorination of 2-thiazolyl cyanomethyl sulfide afforded 5-fluorothiazole and a-fluorinated thiazole derivatives. Thus, the product selectivity was found to be greatly changed by the electron-withdrawing ability of substituents at the side chain of the thiazole ring. This is the first report of a successful anodic fluorination of a thiazole ring.

  DOI：

  10.1021/jo020411t

文献信息

• Electrolytic Partial Fluorination of Organic Compounds. 64.¹ Anodic Mono- and Difluorination of Thiazolyl Sulfides
  作者：Sayed M. Riyadh、Toshio Fuchigami

  DOI：10.1021/jo020411t

  日期：2002.12.1

  The anodic fluorination of 2-thiazolyl methyl sulfide, 2-thiazolyl propargyl sulfide, and 2-thiazolyl acetonyl sulfide was successfully carried out to provide the corresponding 5-fluorothiazole and 2,5,5-trifluorothiazoline derivatives. The latter products were readily hydrolyzed to give isolable 5,5-difluoro-2-hydroxythiazoline derivatives. On the other hand, anodic fluorination of 2-thiazolyl cyanomethyl sulfide afforded 5-fluorothiazole and a-fluorinated thiazole derivatives. Thus, the product selectivity was found to be greatly changed by the electron-withdrawing ability of substituents at the side chain of the thiazole ring. This is the first report of a successful anodic fluorination of a thiazole ring.