N5-(phenylmethyl)-3-[(phenylthio)methyl]-N4-propan-2-ylisoxazole-4,5-dicarboxamide | 958987-74-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N5-(phenylmethyl)-3-[(phenylthio)methyl]-N4-propan-2-ylisoxazole-4,5-dicarboxamide
• 英文别名: 5-N-benzyl-3-(phenylsulfanylmethyl)-4-N-propan-2-yl-1,2-oxazole-4,5-dicarboxamide
• CAS: 958987-74-1
• 化学式: C₂₂H₂₃N₃O₃S
• 分子量: 409.509
• InChiKey: QSWFVCDBEFNMMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 5-(benzylcarbamoyl)-3-(phenylthiomethyl)isoxazole-4-carboxylate 、 异丙胺 以 甲醇 为溶剂， 反应 12.0h， 生成 N5-(phenylmethyl)-3-[(phenylthio)methyl]-N4-propan-2-ylisoxazole-4,5-dicarboxamide
  参考文献：
  名称：

  3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity

  摘要：

  A collection of 91 3-(arylthiomethyl)isoxazole-4,5-dicarboxamides was prepared starting from dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate. The thioether moieties in these compounds were subsequently oxidized to give the corresponding 3-(arylsulfonylmethyl)isoxazole-4,5-dicarboxamides. By carefully controlling stoichiometry and reaction conditions, the C4 and C5 carbomethoxy groups could be differentially derivatized to carboxamides. A total of 182 trisubstituted isoxazoles are reported and deposited in the National Institutes of Health Molecular Repository; an 80 compound subset was evaluated for insecticidal activity.

  DOI：

  10.1021/jf901512t

文献信息

• 3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: Chemoselective Nucleophilic Chemistry and Insecticidal Activity
  作者：Gui J. Yu、Satori Iwamoto、Lori I. Robins、James C. Fettinger、Thomas C. Sparks、Beth A. Lorsbach、Mark J. Kurth

  DOI：10.1021/jf901512t

  日期：2009.8.26

  A collection of 91 3-(arylthiomethyl)isoxazole-4,5-dicarboxamides was prepared starting from dimethyl 3-(chloromethyl)isoxazole-4,5-dicarboxylate. The thioether moieties in these compounds were subsequently oxidized to give the corresponding 3-(arylsulfonylmethyl)isoxazole-4,5-dicarboxamides. By carefully controlling stoichiometry and reaction conditions, the C4 and C5 carbomethoxy groups could be differentially derivatized to carboxamides. A total of 182 trisubstituted isoxazoles are reported and deposited in the National Institutes of Health Molecular Repository; an 80 compound subset was evaluated for insecticidal activity.