ethyl 2-bromo-1,4-benzodioxan-2-carboxylate | 102575-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: ethyl 2-bromo-1,4-benzodioxan-2-carboxylate
• 英文别名: ethyl 3-bromo-2H-1,4-benzodioxine-3-carboxylate
• CAS: 102575-13-3
• 化学式: C₁₁H₁₁BrO₄
• 分子量: 287.11
• InChiKey: RCUARICSYVYMOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-1,4-benzodioxan-2-carboxylate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 355.5h， 生成 N,N-diethyl-2-(2-hydroxyphenoxy)acetamide
  参考文献：
  名称：

  Effect of methoxy substitution on the adrenergic activity of three structurally related .alpha.2-adrenoreceptor antagonists

  摘要：

  We have recently reported the synthesis and alpha 2-antagonist activity of the methoxy derivative 2 [2-(2-methoxy-1,4-benzodioxan-2-yl)-2-imidazoline] and described the enhanced potency of this compound over the parent 1,4-benzodioxan, idazoxan, in reversing the inhibition caused by alpha 2-adrenoreceptor agonists of the electrically induced twitch in the rat or mouse vas deferens. It was of interest to us to discover whether a similar substitution in the structurally related alpha 2-adrenoreceptor antagonists piperoxan, prosympal, and fenmetazole would similarly enhance potency. We subsequently discovered that this was not so and potency was decreased markedly. In particular, that of the methoxy derivative of piperoxan was ca. 220 times less than the parent structure.

  DOI：

  10.1021/jm00159a037
• 作为产物：
  描述：

  1,4-苯并二氧六环-2-甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 5.0h， 以100%的产率得到ethyl 2-bromo-1,4-benzodioxan-2-carboxylate
  参考文献：
  名称：

  Effect of methoxy substitution on the adrenergic activity of three structurally related .alpha.2-adrenoreceptor antagonists

  摘要：

  We have recently reported the synthesis and alpha 2-antagonist activity of the methoxy derivative 2 [2-(2-methoxy-1,4-benzodioxan-2-yl)-2-imidazoline] and described the enhanced potency of this compound over the parent 1,4-benzodioxan, idazoxan, in reversing the inhibition caused by alpha 2-adrenoreceptor agonists of the electrically induced twitch in the rat or mouse vas deferens. It was of interest to us to discover whether a similar substitution in the structurally related alpha 2-adrenoreceptor antagonists piperoxan, prosympal, and fenmetazole would similarly enhance potency. We subsequently discovered that this was not so and potency was decreased markedly. In particular, that of the methoxy derivative of piperoxan was ca. 220 times less than the parent structure.

  DOI：

  10.1021/jm00159a037

文献信息

• STILLINGS M. R.; ENGLAND C. D.; WELBOURN A. P.; SMITH C. F. C., J. MED. CHEM., 29,(1986) N 9, 1780-1783
  作者：STILLINGS M. R.、 ENGLAND C. D.、 WELBOURN A. P.、 SMITH C. F. C.

  DOI：——

  日期：——