2-cyclohexyl glutaconic acid | 250721-73-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-cyclohexyl glutaconic acid
• 英文别名: 2-Cyclohexylpent-2-enedioic acid
• CAS: 250721-73-4
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: ZZSQEERKSITJPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl glutaconic acid 在 乙酰氯 作用下， 反应 72.0h， 以22%的产率得到6-Chloro-3-cyclohexyl-pyran-2-one
  参考文献：
  名称：

  3-Alkyl-6-Chloro-2-pyrones:  Selective Inhibitors of Pancreatic Cholesterol Esterase

  摘要：

  A series of 3-alkyl-6-chloro-2-pyrones with cyclohexane rings tethered to the S-position was synthesized. The tether ranged from 0 to 4 methylene units. Inhibition of pancreatic-cholesterol esterase by this series of pyrones was markedly dependent upon the length of the tether. Dissociation constants as low as 25 nM were observed for 6-chloro-3-(1-ethyl-2-cyclohexyl)-2-pyranone. This class of cholesterol esterase inhibitors functioned as simple competitive inhibitors of substrate binding rather than as suicide substrates or active site inactivators. Trypsin and chymotrypsin were not strongly inhibited by this class of pyrones. Selectivities for cholesterol esterase were greater than 10(3). This is in contrast to 3-aryl-6-chloro-2-pyrones which are nonselective, irreversible inactivators of serine hydrolases, Thus, replacement of the 3-aryl group by an appropriately tethered 3-alkyl ring can produce highly selective inhibitors of cholesterol esterase. A second series of halogen-containing esters was prepared in which cholesterol was esterified with alpha-haloacyl halides. These haloesters were simple substrates of cholesterol esterase with no evidence of irreversible inactivation.

  DOI：

  10.1021/jm990309x
• 作为产物：
  描述：

  (E)-4-Carboxy-4-cyclohexyl-pent-2-enedioic acid 在 盐酸 作用下， 反应 1.0h， 以87%的产率得到2-cyclohexyl glutaconic acid
  参考文献：
  名称：

  3-Alkyl-6-Chloro-2-pyrones:  Selective Inhibitors of Pancreatic Cholesterol Esterase

  摘要：

  A series of 3-alkyl-6-chloro-2-pyrones with cyclohexane rings tethered to the S-position was synthesized. The tether ranged from 0 to 4 methylene units. Inhibition of pancreatic-cholesterol esterase by this series of pyrones was markedly dependent upon the length of the tether. Dissociation constants as low as 25 nM were observed for 6-chloro-3-(1-ethyl-2-cyclohexyl)-2-pyranone. This class of cholesterol esterase inhibitors functioned as simple competitive inhibitors of substrate binding rather than as suicide substrates or active site inactivators. Trypsin and chymotrypsin were not strongly inhibited by this class of pyrones. Selectivities for cholesterol esterase were greater than 10(3). This is in contrast to 3-aryl-6-chloro-2-pyrones which are nonselective, irreversible inactivators of serine hydrolases, Thus, replacement of the 3-aryl group by an appropriately tethered 3-alkyl ring can produce highly selective inhibitors of cholesterol esterase. A second series of halogen-containing esters was prepared in which cholesterol was esterified with alpha-haloacyl halides. These haloesters were simple substrates of cholesterol esterase with no evidence of irreversible inactivation.

  DOI：

  10.1021/jm990309x