1-(2-Allyloxy-4-bromo-phenoxy)-3-isopropylamino-propan-2-ol | 71186-73-7

• 英文名称: 1-(2-Allyloxy-4-bromo-phenoxy)-3-isopropylamino-propan-2-ol
• CAS: 71186-73-7
• 化学式: C₁₅H₂₂BrNO₃
• 分子量: 344.249
• InChiKey: OYPMPRGUCFNFJW-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  1-(2-Allyloxy-4-bromo-phenoxy)-3-isopropylamino-propan-2-ol 在 吡啶盐酸盐 作用下， 生成 5-Bromo-2-(2-hydroxy-3-isopropylamino-propoxy)-phenol
  参考文献：
  名称：

  Metabolism of .beta.-adrenergic antagonists. Evidence for an arene oxide-NIH shift pathway in the aromatic hydroxylation of oxprenolol

  摘要：

  The metabolic hydroxylation of 4'-deuteriooxprenolol [1-(isopropylamino)-3-[2'-(allyloxy)-4'-deuteriophenoxy]-2-propanol] prepared from the 4'-bromo compound was examined in the rat (in vivo). GC-MS analysis of the 4'-and 5'-hydroxyoxprenolol obtained showed 65% retention of deuterium in each of the metabolites. The results indicate that an arene oxide-NIH shift pathway is operative in these hydroxylation processes. The equal magnitude of deuterium retention is supportive of a 4',5'-arene oxide as a major contributor to their formation.

  DOI：

  10.1021/jm00195a015
• 作为产物：
  描述：

  2-(2-Allyloxy-4-bromo-phenoxymethyl)-oxirane 、 异丙胺 生成 1-(2-Allyloxy-4-bromo-phenoxy)-3-isopropylamino-propan-2-ol
  参考文献：
  名称：

  Metabolism of .beta.-adrenergic antagonists. Evidence for an arene oxide-NIH shift pathway in the aromatic hydroxylation of oxprenolol

  摘要：

  The metabolic hydroxylation of 4'-deuteriooxprenolol [1-(isopropylamino)-3-[2'-(allyloxy)-4'-deuteriophenoxy]-2-propanol] prepared from the 4'-bromo compound was examined in the rat (in vivo). GC-MS analysis of the 4'-and 5'-hydroxyoxprenolol obtained showed 65% retention of deuterium in each of the metabolites. The results indicate that an arene oxide-NIH shift pathway is operative in these hydroxylation processes. The equal magnitude of deuterium retention is supportive of a 4',5'-arene oxide as a major contributor to their formation.

  DOI：

  10.1021/jm00195a015