methyl 3,5-diphenyl-5-(p-tolyl)-4,5-dihydroisoxazole-4-carboxylate | 1415035-32-3

• 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: methyl 3,5-diphenyl-5-(p-tolyl)-4,5-dihydroisoxazole-4-carboxylate
• 英文别名: methyl 5-(4-methylphenyl)-3,5-diphenyl-4H-1,2-oxazole-4-carboxylate
• CAS: 1415035-32-3
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: AGSAJXDLAHTMKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 一氧化碳 、 4-iodo-3,5-diphenyl-5-(p-tolyl)-2-tosyl-2,5-dihydroisoxazole 在 palladium diacetate 、 二异丙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、2.03 MPa 条件下， 反应 12.0h， 以51%的产率得到methyl 3,5-diphenyl-5-(p-tolyl)-4,5-dihydroisoxazole-4-carboxylate
  参考文献：
  名称：

  Tandem reaction of propargyl alcohols and N-tosyl hydroxylamine: switchable synthesis of 2,5-dihydroisoxazoles and 4-halo-2,5-dihydroisoxazoles

  摘要：

  2,5-Dihydroisoxazoles, 4-iodo-2,5-dihydroisoxazoles, and 4-bromo-2,5-dihydroisoxazoles were efficiently constructed from propargylic alcohols and N-tosyl hydroxylamine using ytterbium triflate, iodine and N-bromosuccinimide, respectively. N-sulfonylallenamide is postulated to be the key intermediate for these tandem transformations. Moreover, the resulting 4-iodo-2,5-dihydroisoxazoles could be elaborated by palladium-catalyzed carbonylation to generate 4-methoxycarbonyl-4,5-dihydroisoxazoles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.092

文献信息

• Tandem reaction of propargyl alcohols and N-tosyl hydroxylamine: switchable synthesis of 2,5-dihydroisoxazoles and 4-halo-2,5-dihydroisoxazoles
  作者：Yuanxun Zhu、Guangwei Yin、Lang Sun、Ping Lu、Yanguang Wang

  DOI：10.1016/j.tet.2012.09.092

  日期：2012.12

  2,5-Dihydroisoxazoles, 4-iodo-2,5-dihydroisoxazoles, and 4-bromo-2,5-dihydroisoxazoles were efficiently constructed from propargylic alcohols and N-tosyl hydroxylamine using ytterbium triflate, iodine and N-bromosuccinimide, respectively. N-sulfonylallenamide is postulated to be the key intermediate for these tandem transformations. Moreover, the resulting 4-iodo-2,5-dihydroisoxazoles could be elaborated by palladium-catalyzed carbonylation to generate 4-methoxycarbonyl-4,5-dihydroisoxazoles. (C) 2012 Elsevier Ltd. All rights reserved.