1-<2,3-Epoxy-propyloxy>-2-methoxy-4-<3-oxo-butyl>-benzol | 29121-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-<2,3-Epoxy-propyloxy>-2-methoxy-4-<3-oxo-butyl>-benzol
• 英文别名: 4-[3-Methoxy-4-(oxiran-2-ylmethoxy)phenyl]butan-2-one
• CAS: 29121-64-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: IRTSEHUYUWANNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<2,3-Epoxy-propyloxy>-2-methoxy-4-<3-oxo-butyl>-benzol 、 异丙胺 以 乙醇 为溶剂， 以30%的产率得到1-{[4-(3-oxobutyl)-2-methoxy]phenoxy}-3-(isopropylamino)propan-2-ol
  参考文献：
  名称：

  A new aspect of view in synthesizing new type β-adrenoceptor blockers with ancillary antioxidant activities

  摘要：

  A series of vanilloid-type beta -adrenoceptor blockers derived from antioxidant traditional Chinese herbal medicines were synthesized and tested for their antioxidant and adrenoceptor antagonistic activities. They all possessed significant beta -adrenoceptor blocking activities under in vitro experiments and radioligand binding assays. In addition, some compounds were further examined in in vivo tests and produced antagonist effects matching that of propranolol and labetalol by measurements of antagonism coward (-) isoproterenol-induced tachycardia and (-)phenylephrine-induced presser responses in anesthetized rats. Furthermore. all of the compounds had antioxidant effects inherited from their original structures. In conclusion. compound 11 had the most potent beta -adrenoceptors blocking activity. 12 and 13 possessed high cardioselectivity, whereas 14, 15 and 16 possessed additional alpha -adrenoceptor blocking activity and 15 is the most effective antioxidant of all. The antioxidant activity may be due to their alpha and beta unsaturated side chain at position 1 and ortho-substituted methoxy moiety on 4-phenoxyethylamine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00067-0
• 作为产物：
  描述：

  姜酮 、 环氧氯丙烷 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-<2,3-Epoxy-propyloxy>-2-methoxy-4-<3-oxo-butyl>-benzol
  参考文献：
  名称：

  A new aspect of view in synthesizing new type β-adrenoceptor blockers with ancillary antioxidant activities

  摘要：

  A series of vanilloid-type beta -adrenoceptor blockers derived from antioxidant traditional Chinese herbal medicines were synthesized and tested for their antioxidant and adrenoceptor antagonistic activities. They all possessed significant beta -adrenoceptor blocking activities under in vitro experiments and radioligand binding assays. In addition, some compounds were further examined in in vivo tests and produced antagonist effects matching that of propranolol and labetalol by measurements of antagonism coward (-) isoproterenol-induced tachycardia and (-)phenylephrine-induced presser responses in anesthetized rats. Furthermore. all of the compounds had antioxidant effects inherited from their original structures. In conclusion. compound 11 had the most potent beta -adrenoceptors blocking activity. 12 and 13 possessed high cardioselectivity, whereas 14, 15 and 16 possessed additional alpha -adrenoceptor blocking activity and 15 is the most effective antioxidant of all. The antioxidant activity may be due to their alpha and beta unsaturated side chain at position 1 and ortho-substituted methoxy moiety on 4-phenoxyethylamine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00067-0

文献信息

• Ferrari; Ferrini; Casagrande, Bollettino Chimico Farmaceutico, 1968, vol. 107, # 4, p. 234 - 248
  作者：Ferrari、Ferrini、Casagrande

  DOI：——

  日期：——
• A new aspect of view in synthesizing new type β-adrenoceptor blockers with ancillary antioxidant activities
  作者：Yeun-Chih Huang、Bin-Nan Wu、Jwu-Lai Yeh、Sheue-Jiun Chen、Jyh-Chong Liang、Yi-Ching Lo、Ing-Jun Chen

  DOI：10.1016/s0968-0896(01)00067-0

  日期：2001.7

  A series of vanilloid-type beta -adrenoceptor blockers derived from antioxidant traditional Chinese herbal medicines were synthesized and tested for their antioxidant and adrenoceptor antagonistic activities. They all possessed significant beta -adrenoceptor blocking activities under in vitro experiments and radioligand binding assays. In addition, some compounds were further examined in in vivo tests and produced antagonist effects matching that of propranolol and labetalol by measurements of antagonism coward (-) isoproterenol-induced tachycardia and (-)phenylephrine-induced presser responses in anesthetized rats. Furthermore. all of the compounds had antioxidant effects inherited from their original structures. In conclusion. compound 11 had the most potent beta -adrenoceptors blocking activity. 12 and 13 possessed high cardioselectivity, whereas 14, 15 and 16 possessed additional alpha -adrenoceptor blocking activity and 15 is the most effective antioxidant of all. The antioxidant activity may be due to their alpha and beta unsaturated side chain at position 1 and ortho-substituted methoxy moiety on 4-phenoxyethylamine. (C) 2001 Elsevier Science Ltd. All rights reserved.