2,3-dibromo-4'-hydroxyacetophenone | 41877-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dibromo-4'-hydroxyacetophenone
• 英文别名: 4-hydroxy-3-bromophenacyl bromide；ω,3-Dibrom-4-hydroxyacetophenon；2-bromo-1-(3-bromo-4-hydroxy-phenyl)-ethanone；2-Brom-1-(3-brom-4-hydroxy-phenyl)-aethanon；2-Bromo-1-(3-bromo-4-hydroxyphenyl)ethanone
• CAS: 41877-18-3
• 化学式: C₈H₆Br₂O₂
• 分子量: 293.942
• InChiKey: BESUUECFZJZVDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dibromo-4'-hydroxyacetophenone 在 盐酸 、 sodium tetrahydroborate 、 乌洛托品 作用下， 以 水 为溶剂， 反应 10.5h， 生成 α-(aminomethyl)-(3-bromo-4-hydroxyphenyl)methanol
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008
• 作为产物：
  描述：

  2-溴-4'-羟基苯乙酮 在 phenyltrimethylammonium tribromide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 生成 2,3-dibromo-4'-hydroxyacetophenone
  参考文献：
  名称：

  Reactions of 3-Isopropenyl- and 3-Acetyltropolone with Quarternary Ammonium Tribromides

  摘要：

  在四氢呋喃中用季铵三溴化物处理 3-isopenyltropolone 可以得到 3-甲基-8H-环庚烷并[b]呋喃-8-酮。在甲醇-二氯甲烷中的反应得到 7-溴-3-甲基-8H-环庚烷并[b]呋喃-8-酮。3-acetyltropolone 与三溴化物在四氢呋喃中溴化生成 3-（溴乙酰基）tropolone，而在甲醇溶剂中反应生成 7-溴和 5,7- 二溴取代的 3-acetyltropolone。还进行了 4′-羟基苯乙酮的溴化反应。

  DOI：

  10.1246/bcsj.65.295

文献信息

• Rosenmund; Pfroepffer, Chemische Berichte, 1957, vol. 90, p. 1922,1926
  作者：Rosenmund、Pfroepffer

  DOI：——

  日期：——
• Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type
  作者：Gerard Leclerc、Jean Claude Bizec、Nicole Bieth、Jean Schwartz

  DOI：10.1021/jm00181a008

  日期：1980.7

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.
• Reactions of 3-Isopropenyl- and 3-Acetyltropolone with Quarternary Ammonium Tribromides
  作者：Yoichiro Matsunaga、Kimiaki Imafuku

  DOI：10.1246/bcsj.65.295

  日期：1992.1

  Treatments of 3-isopropenyltropolone with quarternary ammonium tribromides in tetrahydrofuran afforded 3-methyl-8H-cyclohepta[b]furan-8-one. The reactions in methanol–dichloromethane gave 7-bromo-3-methyl-8H-cyclohepta[b]furan-8-one. Bromination of 3-acetyltropolone with the tribromides in tetrahydrofuran produced 3-(bromoacetyl)tropolone, while the reaction in the methanolic solvent gave 7-bromo- and 5,7-dibromo-substituted 3-acetyltropolones. The brominations of 4′-hydroxyacetophenone were also carried out.

  在四氢呋喃中用季铵三溴化物处理 3-isopenyltropolone 可以得到 3-甲基-8H-环庚烷并[b]呋喃-8-酮。在甲醇-二氯甲烷中的反应得到 7-溴-3-甲基-8H-环庚烷并[b]呋喃-8-酮。3-acetyltropolone 与三溴化物在四氢呋喃中溴化生成 3-（溴乙酰基）tropolone，而在甲醇溶剂中反应生成 7-溴和 5,7- 二溴取代的 3-acetyltropolone。还进行了 4′-羟基苯乙酮的溴化反应。