4-acetoxy-3,5-dibutyl-6-(2-hydroxypropyl)-2-pyrone | 98420-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-acetoxy-3,5-dibutyl-6-(2-hydroxypropyl)-2-pyrone
• 英文别名: [3,5-Dibutyl-2-(2-hydroxypropyl)-6-oxopyran-4-yl] acetate
• CAS: 98420-36-1
• 化学式: C₁₈H₂₈O₅
• 分子量: 324.417
• InChiKey: OCFGJTQPYXEAAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetoxy-3,5-dibutyl-6-(2-hydroxypropyl)-2-pyrone 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以75.5%的产率得到4-acetoxy-3,5-dibutyl-6-(2-oxopropyl)-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
• 作为产物：
  描述：

  ethyl 2-butyl-3-oxooctanoate 在 palladium on activated charcoal 吡啶 、 正丁基锂 、 4 A molecular sieve 、 2,2'-Dimethyl-5,5'-di-tert-butyl-4,4'-dihydroxy-diphenyl-sulfid, Lanotox 、 氢气 、 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 41.0h， 生成 4-acetoxy-3,5-dibutyl-6-(2-hydroxypropyl)-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