4'-(acetyloxy)-2'-hydroxy-3'-methylacetophenone | 144224-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-(acetyloxy)-2'-hydroxy-3'-methylacetophenone
• 英文别名: (4-Acetyl-3-hydroxy-2-methylphenyl) acetate
• CAS: 144224-86-2
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: BAGBAICTOVSXFH-UHFFFAOYSA-N

物化性质

• 熔点：
  71–73°C
• 沸点：
  336.5±42.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-(acetyloxy)-2'-hydroxy-3'-methylacetophenone 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 7-hydroxy-8-methyl-2-morpholinyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of antiplatelet 2-aminochromones

  摘要：

  The synthesis and biological evaluation of a series of antiplatelet 2-morpholinylchromones has been described. Modification of the C-7 phenylmethoxy group of 8-methyl-7-(phenylmethoxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one (2) has led to the discovery of a series of 7-[(amino-ethyl)oxy]-8-methyl derivatives which are potent inhibitors of ADP-induced platelet aggregation. Several members of this class proved active in preventing platelet-dependent thrombus formation in the dog, including 8-methyl-7-[2-(4-methyl-1-piperazinyl)ethoxy]-2-(4-morpholinyl)-4H-1-benzopyran-4-one (39) which was devoid of hemodynamic effects at the effective antithrombotic dose.

  DOI：

  10.1021/jm00066a012
• 作为产物：
  描述：

  3,5-二羟基-4-乙酰甲苯 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到4'-(acetyloxy)-2'-hydroxy-3'-methylacetophenone
  参考文献：
  名称：

  Synthesis and biological evaluation of antiplatelet 2-aminochromones

  摘要：

  The synthesis and biological evaluation of a series of antiplatelet 2-morpholinylchromones has been described. Modification of the C-7 phenylmethoxy group of 8-methyl-7-(phenylmethoxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one (2) has led to the discovery of a series of 7-[(amino-ethyl)oxy]-8-methyl derivatives which are potent inhibitors of ADP-induced platelet aggregation. Several members of this class proved active in preventing platelet-dependent thrombus formation in the dog, including 8-methyl-7-[2-(4-methyl-1-piperazinyl)ethoxy]-2-(4-morpholinyl)-4H-1-benzopyran-4-one (39) which was devoid of hemodynamic effects at the effective antithrombotic dose.

  DOI：

  10.1021/jm00066a012

文献信息

• A novel synthesis of 2-aminochromones via phosgeniminium salts
  作者：Joel Morris、Donn G. Wishka、Yue Fang

  DOI：10.1021/jo00050a025

  日期：1992.11

  A novel method for the synthesis of antiplatelet 2-aminochromones making use of the reaction of 2'-hydroxyacetophenone-BF2 Complexes with phosgeniminium chlorides has been developed. Aqueous hydrolysis of the intermediate beta-chlorovinylogous amide-BF2 complex affords the 2-aminochromone in good yield, without the need for chromatographic purification.