α-fluoro-α-[2-(4-phenylthiazolyl)thio]acetonitrile | 493046-83-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: α-fluoro-α-[2-(4-phenylthiazolyl)thio]acetonitrile
• 英文别名: Acetonitrile, fluoro[(4-phenyl-2-thiazolyl)thio]-；2-fluoro-2-[(4-phenyl-1,3-thiazol-2-yl)sulfanyl]acetonitrile
• CAS: 493046-83-6
• 化学式: C₁₁H₇FN₂S₂
• 分子量: 250.32
• InChiKey: VEVHMEJYDSKMFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-cyanomethylmercapto-4-phenylthiazole 在 四乙基氟化铵水合物 作用下， 以 乙二醇二甲醚 为溶剂， 以60%的产率得到α-fluoro-α-[2-(4-phenylthiazolyl)thio]acetonitrile
  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.