(4R,5R)-4-(4-Bromo-phenyl)-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester | 145103-57-7

• 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: (4R,5R)-4-(4-Bromo-phenyl)-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester
• 英文别名: methyl (4R,5R)-4-(4-bromophenyl)-5-(hydroxymethyl)-2-oxido-4,5-dihydro-1,2-oxazol-2-ium-3-carboxylate
• CAS: 145103-57-7
• 化学式: C₁₂H₁₂BrNO₅
• 分子量: 330.135
• InChiKey: DQCGMLVKRMXNCA-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-(4-Bromo-phenyl)-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到(4aR,9aR)-7-Bromo-4a,9a-dihydro-1H-benzo[4,5]furo[2,3-c]pyran-3,4-dione 4-oxime
  参考文献：
  名称：

  Part XII of "Synthetic Reactions of Isoxazoline 2-Oxides." Formation of Benzofuro(2,3-c)tetrahydropyran-3,4-dione 4-Oximes from 4-Substituted 5-Hydroxymethyl-3-methoxycarbonyl-2-isoxazoline 2-Oxides.

  摘要：

  4-Substituted 5-hydroxymethyl-3-methoxycarbonyl-2-isoxazoline 2-oxides (1) reacted with an excess of titanium tetrachloride in dichloromethane to yield a new type of functionalized heterocycle, benzofuro[2, 3-c]tetrahydropyran-3, 4-dione 4-oximes (2). The structure of the 7-chloro derivative (2a) was determined by single crystal X-ray analysis and a mechanism is proposed for the formation of 2 from 1.

  DOI：

  10.1248/cpb.41.1848
• 作为产物：
  描述：

  3,5-bis(methoxycarbonyl)-4-p-bromophenyl-2-isoxazoline-2-oxide 在 Bn₄NCl sodium tetrahydroborate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以60%的产率得到(4R,5R)-4-(4-Bromo-phenyl)-5-hydroxymethyl-2-oxy-4,5-dihydro-isoxazole-3-carboxylic acid methyl ester
  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