(2-(4-chlorophenyl)oxazol-5-yl)(4-fluorophenyl)methanone | 1492785-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-(4-chlorophenyl)oxazol-5-yl)(4-fluorophenyl)methanone
• CAS: 1492785-91-7
• 化学式: C₁₆H₉ClFNO₂
• 分子量: 301.704
• InChiKey: JHBIMLBGIWEJQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2-(4-chlorophenyl)oxazol-5-yl)(4-fluorophenyl)methanone 、 3-溴环己烯 在 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 、 copper(I) cyanide di(lithium chloride) 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 以74%的产率得到(2-(4-chlorophenyl)-4-(cyclohex-2-en-1-yl)oxazol-5-yl)(4-fluorophenyl)methanone
  参考文献：
  名称：

  Regioselective Functionalization of the Oxazole Scaffold Using TMP-Bases of Mg and Zn

  摘要：

  A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl center dot LiCl or TMPZnCl center dot LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.

  DOI：

  10.1021/ol403019c
• 作为产物：
  描述：

  对氯碘苯 在 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 (2-(4-chlorophenyl)oxazol-5-yl)(4-fluorophenyl)methanone
  参考文献：
  名称：

  Regioselective Functionalization of the Oxazole Scaffold Using TMP-Bases of Mg and Zn

  摘要：

  A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl center dot LiCl or TMPZnCl center dot LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.

  DOI：

  10.1021/ol403019c