1-(3-Butan-2-yl-2,4-dihydroxyphenyl)ethanone | 79557-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-Butan-2-yl-2,4-dihydroxyphenyl)ethanone
• CAS: 79557-74-7
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: NKTFJDJAKQGLMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  1-(3-Butan-2-yl-2,4-dihydroxyphenyl)ethanone 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-2-butan-2-yl-3-hydroxyphenoxy)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， 生成 1-(3-Butan-2-yl-2,4-dihydroxyphenyl)ethanone
  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

• Phenol derivatives, processes for their preparation and pharmaceutical compositions containing them
  申请人：GLAXO GROUP LIMITED

  公开号：EP0028063A1

  公开（公告）日：1981-05-06

  Compounds are disclosed which are phenoxyalkoxyphenyl derivatives of general formula (I) wherein Y represents the group -A, -ZA or OZ1A where A represents a carboxylic acid group, a 5-1H-tetrazolyf ring or a N-5-1 H-tetrazolylcarboxamide group; Z represents a Ci-4 alkylene, C2-4 alkenylene or C2-4 alkynylene chain optionally substituted by one or more C1-3 alkyl groups and Z1 represents a C1-4 alkylene chain optionally substituted by one or more C1-3 alkyl groups; X represents a C1-10 carbon chain which may be saturated or unsaturated in the case of chains containing at least 4 carbon atoms, and may be substituted by a hydroxy group or by one or more C1-3 alkyl groups, which chain may be interrupted by a benzene ring which may be linked through its 1- and 2-, 1- and 3-, or 1- and 4-positions; R1 represents a hydrogen atom or a C1-6 alkyl group; R2 represents the group -COR6 where R6 represents a hydrogen atom, an aryl group or a C1-6 alkyl group which may be substituted by an aryl group; R3 represents a C1-6 alkyl group or a C3-6 alkenyl group; and R4 and R5 which may be the same or different, each represents a hydrogen atom, a halogen atom or a hydroxy, Ci-3 alkoxy, C1-6 alkyl, C3-C6 alkenyl, C1-3 alkanoyl, nitro or carboxylic acid group with the proviso that R4 and R5 cannot both be nitro, alkanoyl or carboxylic acid groups, and physologically acceptable salts thereof. The compounds are potent antagonists of the action of slow reacting substance of anaphylaxis and are thus indicated for use in the treatment of obstructive airways diseases such as asthma and hay fever and in skin afflictions.

  所公开的化合物是通式(I)的苯氧基烷氧基苯基衍生物 其中 Y 代表基团-A、-ZA 或 OZ1A，其中 A 代表羧酸基团、5-1H-四氮唑环或 N-5-1 H-四氮唑甲酰胺基团； Z 代表任选被一个或多个 C1-3 烷基取代的 Ci-4亚烷基、C2-4 亚烯基或 C2-4 亚炔基链，Z1 代表任选被一个或多个 C1-3 烷基取代的 C1-4 亚烷基链； X 代表 C1-10 碳链，可以是饱和的 或不饱和（如果链中至少含有 4 个碳原子），并可被羟基取代 或一个或多个 C1-3 烷基基团取代，该链可 可被一个苯环打断，该苯环可通过以下方式连接 1-位和 2-位、1-位和 3-位或 1-位和 4-位相连； R1 代表氢原子或 C1-6 烷基； R2 代表基团-COR6，其中 R6 代表氢原子、芳基或可被芳基取代的 C1-6 烷基； R3 代表 C1-6 烷基或 C3-6 烯基；以及 R4和R5可以相同或不同，各自代表氢原子、卤素原子或羟基、Ci-3烷氧基、C1-6烷基、C3-C6烯基、C1-3烷酰基、硝基或羧酸基团，但R4和R5不能都是硝基、烷酰基或羧酸基团，以及它们的物理上可接受的盐。 这些化合物是过敏性休克慢反应物质的强效拮抗剂，因此可用于治疗阻塞性呼吸道疾病，如哮喘和花粉症，以及皮肤病。
• 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.