3-Methyl-5-styrylisoxazol | 51101-01-0

• 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: 3-Methyl-5-styrylisoxazol
• 英文别名: 3-methyl-5-styryl-isoxazole；3-Methyl-5-styrylisoxazole；3-methyl-5-(2-phenylethenyl)-1,2-oxazole
• CAS: 51101-01-0
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: HPEIOZLJNFUVJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二甲基异唑 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 3-Methyl-5-styrylisoxazol
  参考文献：
  名称：

  Styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles. Novel 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A series of styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles were prepared and found to be dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia cells. Compounds from this series also were found to inhibit the in vivo production of LTB4 when dosed orally in rats. Among these compounds, di-tert-butylphenols 19 and 33 exhibit oral activity in various models of inflammation and, most importantly, are devoid of ulcerogenic potential.

  DOI：

  10.1021/jm00106a006

文献信息

• The Synthesis of 3-Methyl-5-(2-aminoalkyl)isoxazoles
  作者：Choji Kashima、Yoshihiko Tsuda

  DOI：10.1246/bcsj.46.3533

  日期：1973.11

  bases gave 3-methyl-5-(2-aminoalkyl)isoxazole derivatives in the presence of sodium amide in liquid ammonia. The N-alkylation on the anilino group of 3-methyl-5-(2-anilino-2-phenylethyl)isoxazole resulted in deamination, thus giving 3-methyl-5-styrylisoxazole. The reaction of 3,5-dimethylisoxazole with benzonitrile gave 3-methyl-5-(2-aminostyryl)isoxazole, which was then reduced to 3-methyl-5-(2-amino

  3,5-二甲基异恶唑与Scruff碱的反应在氨钠存在下在液氨中得到3-甲基-5-(2-氨基烷基)异恶唑衍生物。3-甲基-5-(2-苯胺基-2-苯基乙基)异恶唑的苯胺基上的N-烷基化导致脱氨基，从而得到3-甲基-5-苯乙烯基异恶唑。3,5-二甲基异恶唑与苄腈反应生成3-甲基-5-(2-氨基苯乙烯基)异恶唑，然后将其还原为3-甲基-5-(2-氨基-2-苯基乙基)异恶唑。
• Search for α-adrenoblockers among β(γ)-dialkylaminoalkyl derivatives of hydroxystyrylisoxazoles
  作者：S. D. Sokolov、B. A. Medvedev、S. M. Vinogradova、O. G. Azarevich、M. V. Berg、M. D. Mashkovskii

  DOI：10.1007/bf00778974

  日期：1991.12
• Styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles. Novel 5-lipoxygenase and cyclooxygenase inhibitors
  作者：Daniel L. Flynn、Thomas R. Belliotti、Amal M. Boctor、David T. Connor、Catherine R. Kostlan、Donald E. Nies、Daniel F. Ortwine、Denis J. Schrier、Jagadish C. Sircar

  DOI：10.1021/jm00106a006

  日期：1991.2

  A series of styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles were prepared and found to be dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia cells. Compounds from this series also were found to inhibit the in vivo production of LTB4 when dosed orally in rats. Among these compounds, di-tert-butylphenols 19 and 33 exhibit oral activity in various models of inflammation and, most importantly, are devoid of ulcerogenic potential.