3'-(iso-Butyl)-2',4'-dihydroxyacetophenone | 118604-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-(iso-Butyl)-2',4'-dihydroxyacetophenone
• 英文别名: 1-[2,4-dihydroxy-3-(2-methylpropyl)phenyl]ethanone
• CAS: 118604-46-9
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: HSAFBDJQKZPBCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-(iso-Butyl)-2',4'-dihydroxyacetophenone 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 生成 4-[[4-Acetyl-3-hydroxy-2-(2-methylpropyl)phenoxy]methyl]-3-methoxybenzoic acid
  参考文献：
  名称：

  Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes

  摘要：

  Considerations of the possible similarities between leukotriene D4 and its prototypical antagonist, FPL 55712, led to the development of a new series of leukotriene antagonists incorporating a hydroxyacetophenone group (e.g., the toluic acids 16 and 18). Although considerable attention has focused on FPL 55712-derived analogues, only limited investigations into alternatives for the standard 4-acetyl-3-hydroxy-2-propylphenoxy moiety have been reported. Therefore, an extensive study of modifications to the hydroxyacetophenone portion of toluic acid 18 was undertaken. Although no viable alternative to the 3-hydroxy moiety was discovered, replacements for the 2-propyl group (34, 37) and the 4-acetyl functionality (56, 59) yielded potent antagonists. A number of compounds exhibited longer duration of action in vivo than FPL 55712.

  DOI：

  10.1021/jm00124a014
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 49.0h， 生成 3'-(iso-Butyl)-2',4'-dihydroxyacetophenone
  参考文献：
  名称：

  Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes

  摘要：

  Considerations of the possible similarities between leukotriene D4 and its prototypical antagonist, FPL 55712, led to the development of a new series of leukotriene antagonists incorporating a hydroxyacetophenone group (e.g., the toluic acids 16 and 18). Although considerable attention has focused on FPL 55712-derived analogues, only limited investigations into alternatives for the standard 4-acetyl-3-hydroxy-2-propylphenoxy moiety have been reported. Therefore, an extensive study of modifications to the hydroxyacetophenone portion of toluic acid 18 was undertaken. Although no viable alternative to the 3-hydroxy moiety was discovered, replacements for the 2-propyl group (34, 37) and the 4-acetyl functionality (56, 59) yielded potent antagonists. A number of compounds exhibited longer duration of action in vivo than FPL 55712.

  DOI：

  10.1021/jm00124a014

文献信息

• Process for leukotriene antagonists
  申请人：Eli Lilly and Company

  公开号：US04777299A1

  公开（公告）日：1988-10-11

  1,3-Dialkylbenzenes are acylated and deprotected in a mixture of acetic or propionic acid and hydrobromic acid. The dihydroxyphenones thus produced are intermediates in the synthesis of leukotriene antagonists.

  1,3-二烷基苯被酰化并在乙酸或丙酸和氢溴酸的混合物中去保护。因此产生的二羟基苯酮是白三烯拮抗剂合成中的中间体。
• Process for intermediates to leukotriene antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0295882B1

  公开（公告）日：1991-08-21
• US4777299A
  申请人：——

  公开号：US4777299A

  公开（公告）日：1988-10-11
• Hydroxyacetophenone-derived antagonists of the peptidoleukotrienes
  作者：Frederick J. Brown、Peter R. Bernstein、Laura A. Cronk、David L. Dosset、Kevin C. Hebbel、Thomas P. Maduskuie、Howard S. Shapiro、Edward P. Vacek、Ying K. Yee

  DOI：10.1021/jm00124a014

  日期：1989.4

  Considerations of the possible similarities between leukotriene D4 and its prototypical antagonist, FPL 55712, led to the development of a new series of leukotriene antagonists incorporating a hydroxyacetophenone group (e.g., the toluic acids 16 and 18). Although considerable attention has focused on FPL 55712-derived analogues, only limited investigations into alternatives for the standard 4-acetyl-3-hydroxy-2-propylphenoxy moiety have been reported. Therefore, an extensive study of modifications to the hydroxyacetophenone portion of toluic acid 18 was undertaken. Although no viable alternative to the 3-hydroxy moiety was discovered, replacements for the 2-propyl group (34, 37) and the 4-acetyl functionality (56, 59) yielded potent antagonists. A number of compounds exhibited longer duration of action in vivo than FPL 55712.