4-hydroxy-3-methyl-6-phenacetyl-2-pyrone | 24607-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-3-methyl-6-phenacetyl-2-pyrone
• 英文别名: 4-Hydroxy-3-methyl-6-phenacylpyran-2-one
• CAS: 24607-33-8
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: KOTFPNOCGYLHOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-hydroxy-3-methyl-6-phenacetyl-2-pyrone 在 lithium hydride 作用下， 生成 2,4,6-三羟基-3-甲基-二苯甲酮
  参考文献：
  名称：

  4-羟基-6-苯甲酰基-2-吡喃酮及相关化合物的芳构化反应

  摘要：

  用各种酸性和碱性试剂处理标题化合物导致内酯环裂解形成不稳定的中间体，该中间体以几种方式再循环。用强酸，该化合物被转化为γ-吡喃酮，亲核性碱被转化为间苯二酚，非亲核性碱转化为苯甲酰基间苯三酚。在前两个反应中，相应的3,5,7-三酮酸或酯是中间体。使用大量过量的螯合金属离子（Ca ++）导致可分离量的酯积累。提出了一种烯酮衍生物作为形成苯甲酰基间苯三酚的中间体。已经探索了标题吡喃酮的四种衍生物的反应。

  DOI：

  10.1016/s0040-4020(01)98735-6
• 作为产物：
  描述：

  苯甲酸甲酯 、 3,6-二甲基-4-羟基-2-吡喃酮 在 lithium diisopropyl amide 作用下， 生成 4-hydroxy-3-methyl-6-phenacetyl-2-pyrone
  参考文献：
  名称：

  Inhibition of human leukocyte elastase, porcine pancreatic elastase, and chymotrypsin by elasnin and other 4-hydroxy-2-pyrones

  摘要：

  Elasnin and 15 related 4-hydroxy-2-pyrones have been assayed for in vitro inhibition of human leukocyte elastase, porcine pancreatic elastase, and bovine chymotrypsin. Inhibition constants for HL elastase range from 0.1 to 10 mM. The principal determinant of potency against the elastases is probably the substituent at position 3, which may account for the observed strong homology between the elastases in their inhibition by these compounds. Acetylation of the 4-hydroxy group has no effect on inhibition. The inhibition is noncovalent; there is no evidence of enzyme acylation by these pyrones.

  DOI：

  10.1021/jm00150a013

文献信息

• Inhibition of human leukocyte elastase, porcine pancreatic elastase, and chymotrypsin by elasnin and other 4-hydroxy-2-pyrones
  作者：Robin W. Spencer、Leslie J. Copp、Jurg R. Pfister

  DOI：10.1021/jm00150a013

  日期：1985.12

  Elasnin and 15 related 4-hydroxy-2-pyrones have been assayed for in vitro inhibition of human leukocyte elastase, porcine pancreatic elastase, and bovine chymotrypsin. Inhibition constants for HL elastase range from 0.1 to 10 mM. The principal determinant of potency against the elastases is probably the substituent at position 3, which may account for the observed strong homology between the elastases in their inhibition by these compounds. Acetylation of the 4-hydroxy group has no effect on inhibition. The inhibition is noncovalent; there is no evidence of enzyme acylation by these pyrones.
• Aromatization reactions of 4-hydroxy-6-phenacyl-2-pyrone and related compounds
  作者：T.M. Harris、M.P. Wachter

  DOI：10.1016/s0040-4020(01)98735-6

  日期：1970.1

  Treatment of the title compound with various acidic and basic reagents brought about cleavage of the lactone ring to form unstable intermediates which recyclized in several manners. With strong acids the compound was transformed to γ-pyrones, with nucleophilic bases to resorcinols, and with non-nucleophilic bases to benzoylphloroglucinol. In the first two reactions the corresponding 3,5,7-triketo acid

  用各种酸性和碱性试剂处理标题化合物导致内酯环裂解形成不稳定的中间体，该中间体以几种方式再循环。用强酸，该化合物被转化为γ-吡喃酮，亲核性碱被转化为间苯二酚，非亲核性碱转化为苯甲酰基间苯三酚。在前两个反应中，相应的3,5,7-三酮酸或酯是中间体。使用大量过量的螯合金属离子（Ca ++）导致可分离量的酯积累。提出了一种烯酮衍生物作为形成苯甲酰基间苯三酚的中间体。已经探索了标题吡喃酮的四种衍生物的反应。