benzyl 2,5-dihydro-4-((E)-2-(methoxycarbonyl)ethenyl)-3-phenyl-2H-isoxazole-2-carboxylate | 1287769-33-8

• 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: benzyl 2,5-dihydro-4-((E)-2-(methoxycarbonyl)ethenyl)-3-phenyl-2H-isoxazole-2-carboxylate
• 英文别名: benzyl 4-[(E)-3-methoxy-3-oxoprop-1-enyl]-3-phenyl-5H-1,2-oxazole-2-carboxylate
• CAS: 1287769-33-8
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: UWNVJMLJAUIANK-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [3-(氨基氧基)-1-丙炔-1-基]苯 在 bis-triphenylphosphine-palladium(II) chloride 、 碳酸氢钠 、 三乙胺 、 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 benzyl 2,5-dihydro-4-((E)-2-(methoxycarbonyl)ethenyl)-3-phenyl-2H-isoxazole-2-carboxylate
  参考文献：
  名称：

  Iodocyclization of Hydroxylamine Derivatives Based on the Control of Oxidative Aromatization Leading to 2,5-Dihydroisoxazoles and Isoxazoles

  摘要：

  An efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2,5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2,5-dihydro-derivative.

  DOI：

  10.1021/jo200407b

文献信息

• Iodocyclization of Hydroxylamine Derivatives Based on the Control of Oxidative Aromatization Leading to 2,5-Dihydroisoxazoles and Isoxazoles
  作者：Takashi Okitsu、Kana Sato、Taterao M. Potewar、Akimori Wada

  DOI：10.1021/jo200407b

  日期：2011.5.6

  An efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2,5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2,5-dihydro-derivative.