5-fluoro-2,4-diphenylthiazole | 951000-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-fluoro-2,4-diphenylthiazole
• CAS: 951000-48-9
• 化学式: C₁₅H₁₀FNS
• 分子量: 255.316
• InChiKey: OKSFKYUJIYTRNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,4-diphenylthiazole 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 5-fluoro-2,4-diphenylthiazole
  参考文献：
  名称：

  五元杂芳基溴化物的钯催化氟化深度评估

  摘要：

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

  DOI：

  10.1021/acs.organomet.5b00631

文献信息

• Nuclear fluorination of 2,4-diarylthiazoles with Accufluor®
  作者：Timmeda F. Campbell、Chad E. Stephens

  DOI：10.1016/j.jfluchem.2006.08.007

  日期：2006.12

  A series of 2,4-diphenylthiazole derivatives were synthesized and directly fluorinated at the 5-position by reaction with the N-F fluorinating reagent Accufluor (R). Although fluorination occurred selectively at the thiazole ring, it was always incomplete and thus yields for the novel fluorinated products were low to moderate (19-43%) following purification to remove starting material. Nonetheless, the target compounds were obtained in a convenient and straightforward manner. Selectfluor (R) was not as effective as Accufluor (R) as it gave a trace amount of the 5-chlorothiazole that was difficult to remove by chromatography. (c) 2006 Elsevier B.V. All rights reserved.