4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate | 145103-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate
• CAS: 145103-58-8
• 化学式: C₁₃H₁₄BrNO₇S
• 分子量: 408.227
• InChiKey: CQOAWXKLLJSEJG-GHMZBOCLSA-N

反应信息

• 作为反应物：
  描述：

  4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到4-(4-bromo-2-chlorophenyl)-5-hydroxy-3-methoxycarbonyl-5,6-dihydro-4H-1,2-oxazine
  参考文献：
  名称：

  TiCl4 Promoted Ring Expansion Reactions of 5-Hydroxymethyl-2-isoxazoline-2-oxide Methanesulfonates

  摘要：

  5-Hydroxymethyl-2-isoxazoline-2-oxide methanesulfonates(1) possessing a substituted phenyl ring were treated with TiCl4 to afford either benzofuro[3,2-d]-1,2-oxazines(3) or 4-o-chlorophenyl-5,6-dihydro-4H-1,2-oxazines(4), depending on the nature of the substituents on the phenyl ring of 1. The reaction mechanism of the formation of 3 and 4 is proposed, including 3H-indole-1-oxide zwitterion(B) as a key intermediate.

  DOI：

  10.3987/com-93-6469
• 作为产物：
  描述：

  3,5-bis(methoxycarbonyl)-4-p-bromophenyl-2-isoxazoline-2-oxide 在 Bn₄NCl 吡啶 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 4-p-bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate
  参考文献：
  名称：

  Synthetic Reactions of Isoxazoline-2-oxides. Part VIII. Formation of 4-p-Bromophenyl-5-hydroxy-3-methoxycarbonyl-5,6-dihydro-4H-1,2-oxazine by Means of New Ring Transformation of an Isoxazoline-2-oxide.

  摘要：

  4-p-Bromophenyl-5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline-2-oxide methanesulfonate (1c) reacted with excess titanium tetrabromide in dichloromethane to yield a novel ring transformation product, 4-p-bromophenyl-5-hydroxy-3-methoxycarbonyl-5, 6-dihydro-4H-1, 2-oxazine (2). The structural determination of 2 by single-crystal X-ray analysis is reported.

  DOI：

  10.1248/cpb.40.1921