5-Chloro-2-[2-(3-methoxyphenyl)ethenyl]-1,3-benzoxazole | 879424-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5-Chloro-2-[2-(3-methoxyphenyl)ethenyl]-1,3-benzoxazole
• 英文别名: 5-chloro-2-[2-(3-methoxyphenyl)ethenyl]-1,3-benzoxazole
• CAS: 879424-17-6
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: XWVDCEDYTXDLEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴-2-硝基苯酚 在 盐酸 、 tin(II) chloride dihdyrate 、 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 5-Chloro-2-[2-(3-methoxyphenyl)ethenyl]-1,3-benzoxazole
  参考文献：
  名称：

  Mass spectra of halogenostyrylbenzoxazoles

  摘要：

  Several series of styrylbenzoxazoles of general formula XC6H3(NCO)CH=CHC6H4Y [X= F, Cl or Br; Y = H, F, Cl, Br, CH3 or CH3O] have been investigated by positive ion electrospray and electron ionization mass spectrometry. These compounds, many of which are biologically active or have pharmaceutical potential, show in their electrospray spectra strong peaks for MH+ ions, which undergo relatively little fragmentation. The electron ionization spectra are extremely clean, being dominated by the loss of an atom or radical, Y*, from the ortho position of the pendant ring, by a rearrangement that may be interpreted as a proximity effect. The resultant [M-Y](+) ions are exceptionally stable and rarely undergo further fragmentation. The analytical value of this proximity effect, which is analogous to intramolecular aromatic substitution, in revealing the presence of a substituent in the pendant ring and determining its position, is emphasized. Elimination of a species (including H* or F*) derived from an ortho substituent in the pendant ring occurs even when apparently more favourable alternative fragmentation is possible by direct cleavage of the C-X bond (X = Cl or Br) in the benzoxazole ring. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijms.2012.08.016