3-(chloromethyl)-5-(trifluoromethyl)-2-propanone | 102587-07-5

• 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-(chloromethyl)-5-(trifluoromethyl)-2-propanone
• 英文别名: 3-(Chloromethyl)-5-(trifluoromethyl)pyran-2-one
• CAS: 102587-07-5
• 化学式: C₇H₄ClF₃O₂
• 分子量: 212.556
• InChiKey: ZMBRZQCIEXRNAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(chloromethyl)-5-(trifluoromethyl)-2-propanone 在 magnesium 、 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 3-苄基-5-(三氟甲基)-2-吡喃酮
  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
• 作为产物：
  描述：

  二氯甲基醚 、 5-(三氟甲基)吡喃-2-酮 在 硫酸 作用下， 反应 7.0h， 以50.1%的产率得到3-(chloromethyl)-5-(trifluoromethyl)-2-propanone
  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：——