(3-methyl-5-styryl-isoxazol-4-ylamino)-acetic acid | 1443511-56-5

• 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: (3-methyl-5-styryl-isoxazol-4-ylamino)-acetic acid
• CAS: 1443511-56-5
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: GZQHFHQSEAPTIR-BQYQJAHWSA-N

物化性质

• 沸点：
  514.8±50.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.36
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-甲基靛红 、 (3-methyl-5-styryl-isoxazol-4-ylamino)-acetic acid 、 1,4-萘醌 在 ammonium cerium (IV) nitrate 、 氧气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以90%的产率得到(E)-5'-methyl-2-(3-methyl-5-styrylisoxazol-4-yl)-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione
  参考文献：
  名称：

  A facile synthesis, anti-inflammatory and analgesic activity of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3′-indoline]-2′,4,9-triones

  摘要：

  A new series of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-triones (14) were synthesized by reaction of 4-amino-3-methyl-5-styrylisoxazole 10 with chloroacetic acid followed by a three component reaction with substituted isatins 12 and 1,4-naphthoquinone 13 using Ceric ammonium nitrate (CAN) catalyst under aerial oxidation condition. Structures of these compounds were established on the basis of IR, H-1 NMR, C-13 NMR and mass spectral data. The title compounds 14a-j were evaluated for their anti-inflammatory and analgesic activity. Compounds 14d, 14e and 14f exhibited potent anti-inflammatory and analgesic activity as that of standard drugs. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.053
• 作为产物：
  描述：

  4-amino-3-methyl-5-styrylisoxazole 、 氯乙酸 以 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到(3-methyl-5-styryl-isoxazol-4-ylamino)-acetic acid
  参考文献：
  名称：

  A facile synthesis, anti-inflammatory and analgesic activity of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3′-indoline]-2′,4,9-triones

  摘要：

  A new series of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-triones (14) were synthesized by reaction of 4-amino-3-methyl-5-styrylisoxazole 10 with chloroacetic acid followed by a three component reaction with substituted isatins 12 and 1,4-naphthoquinone 13 using Ceric ammonium nitrate (CAN) catalyst under aerial oxidation condition. Structures of these compounds were established on the basis of IR, H-1 NMR, C-13 NMR and mass spectral data. The title compounds 14a-j were evaluated for their anti-inflammatory and analgesic activity. Compounds 14d, 14e and 14f exhibited potent anti-inflammatory and analgesic activity as that of standard drugs. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.053