acetonyl 2-(4-phenylthiazolyl) sulfide | 22997-33-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: acetonyl 2-(4-phenylthiazolyl) sulfide
• 英文别名: 2-Acetonylmercapto-4-phenyl-thiazol；4-Phenyl-2-(2-oxo-propylmercapto)-thiazol；1-(4-phenyl-thiazol-2-ylsulfanyl)-propan-2-one；1-[(4-Phenyl-1,3-thiazol-2-yl)sulfanyl]propan-2-one
• CAS: 22997-33-7
• 化学式: C₁₂H₁₁NOS₂
• 分子量: 249.357
• InChiKey: OYFWJMUZDQICAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetonyl 2-(4-phenylthiazolyl) sulfide 在 triethylamine pentahydrogen fluoride salt 作用下， 以 乙二醇二甲醚 、 正己烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 2-acetonylthio-5,5-difluoro-2-hydroxy-4-phenyl-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 、 一氯丙酮 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到acetonyl 2-(4-phenylthiazolyl) sulfide
  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

• Thiazolo[2,3-b]thiazolium cation. A new aromatic system
  作者：Charles K. Bradsher、William Jonas Jones

  DOI：10.1021/jo01282a005

  日期：1967.7
• 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.