benzyl 2,5-dihydro-3-phenyl-4-(2-thienyl)-2H-isoxazole-2-carboxylate | 1287769-32-7

• 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: benzyl 2,5-dihydro-3-phenyl-4-(2-thienyl)-2H-isoxazole-2-carboxylate
• 英文别名: benzyl 3-phenyl-4-thiophen-2-yl-5H-1,2-oxazole-2-carboxylate
• CAS: 1287769-32-7
• 化学式: C₂₁H₁₇NO₃S
• 分子量: 363.437
• InChiKey: ZAPWBLXFSYEUIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [3-(氨基氧基)-1-丙炔-1-基]苯 在 碳酸氢钠 、 sodium carbonate 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 benzyl 2,5-dihydro-3-phenyl-4-(2-thienyl)-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.