3-[(4-hydroxyphenyl)methyl]-5-(trifluoromethyl)-2-pyranone | 102681-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-[(4-hydroxyphenyl)methyl]-5-(trifluoromethyl)-2-pyranone
• 英文别名: 3-(4-Hydroxy-benzyl)-5-trifluoromethyl-pyran-2-one；3-[(4-hydroxyphenyl)methyl]-5-(trifluoromethyl)pyran-2-one
• CAS: 102681-98-1
• 化学式: C₁₃H₉F₃O₃
• 分子量: 270.208
• InChiKey: CJBGMTDYYJWIDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-(三氟甲基)吡喃-2-酮 在 硫酸 、 氢溴酸 、 magnesium 、 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 11.0h， 生成 3-[(4-hydroxyphenyl)methyl]-5-(trifluoromethyl)-2-pyranone
  参考文献：
  名称：

  5-(Halomethyl)-2-pyranones as irreversible inhibitors of .alpha.-chymotrypsin

  摘要：

  A series of 5-(halomethyl)-2-pyranones were prepared and assayed as potential mechanism-based inhibitors of chymotrypsin, in order to test whether substitution of a suitable electron-withdrawing group at position 5 in a 2-pyranone can activate the ring for catalytic hydrolysis, as well as form a mechanism-based inhibitor. 3-Benzyl-5-(chloromethyl)-2-pyranone (3) and 3-(1-naphthylmethyl)-5-(chloromethyl)-2-pyranone (4) rapidly and irreversibly inactivate chymotrypsin with high efficiency (I/E = 2.0 for 3 and 1.38 for 4). However, evidence for their formation of an acyl enzyme is lacking, and thus they may simply be active-site alkylating agents. 6-Methyl substitution on 4, or replacement of the chloromethyl of 3 with CF3, prevents inactivation. Since 6-bromo substitution is capable of ring activation, but 5-bromo substitution (3-benzyl-5-bromo-2-pyranone (11)) is not, the 5-position of the pyrone does not appear to affect catalytic hydrolysis.

  DOI：

  10.1021/jm00158a027

文献信息

• BOULANGER W. A.; KATZENELLENBOGEN J. A., J. MED. CHEM., 29,(1986) N 8, 1483-1487
  作者：BOULANGER W. A.、 KATZENELLENBOGEN J. A.

  DOI：——

  日期：——
• 5-(Halomethyl)-2-pyranones as irreversible inhibitors of .alpha.-chymotrypsin
  作者：William A. Boulanger、John A. Katzenellenbogen

  DOI：10.1021/jm00158a027

  日期：1986.8

  A series of 5-(halomethyl)-2-pyranones were prepared and assayed as potential mechanism-based inhibitors of chymotrypsin, in order to test whether substitution of a suitable electron-withdrawing group at position 5 in a 2-pyranone can activate the ring for catalytic hydrolysis, as well as form a mechanism-based inhibitor. 3-Benzyl-5-(chloromethyl)-2-pyranone (3) and 3-(1-naphthylmethyl)-5-(chloromethyl)-2-pyranone (4) rapidly and irreversibly inactivate chymotrypsin with high efficiency (I/E = 2.0 for 3 and 1.38 for 4). However, evidence for their formation of an acyl enzyme is lacking, and thus they may simply be active-site alkylating agents. 6-Methyl substitution on 4, or replacement of the chloromethyl of 3 with CF3, prevents inactivation. Since 6-bromo substitution is capable of ring activation, but 5-bromo substitution (3-benzyl-5-bromo-2-pyranone (11)) is not, the 5-position of the pyrone does not appear to affect catalytic hydrolysis.