2-heptyl-6,7-dihydro-8(8aH)-hydroxy-3-methyl-4H-pyrrole[2,1-b][1,3]oxazine-4-one | 868539-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-heptyl-6,7-dihydro-8(8aH)-hydroxy-3-methyl-4H-pyrrole[2,1-b][1,3]oxazine-4-one
• CAS: 868539-03-1
• 化学式: C₁₅H₂₅NO₃
• 分子量: 267.368
• InChiKey: IFCFXXJFWBVADR-UHFFFAOYSA-N

物化性质

• 沸点：
  432.8±45.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-heptyl-6,7-dihydro-8(8aH)-hydroxy-3-methyl-4H-pyrrole[2,1-b][1,3]oxazine-4-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 41.0h， 生成 2-Heptyl-3-methyl-6,7-dihydro-pyrrolo[2,1-b][1,3]oxazine-4,8-dione
  参考文献：
  名称：

  Novel Inhibitors of the Mitochondrial Respiratory Chain:  Oximes and Pyrrolines Isolated from Penicillium brevicompactum and Synthetic Analogues

  摘要：

  The capacity of inhibition of the mammalian mitochondrial respiratory chain of brevioxime 5a, a natural insecticide compound isolated from Penicillium brevicompactum culture broth, and another 15 analogue compounds, other oximes 5b and 5c; two diastereomeric pyrrolidines 1c' and 1c"; five pyrrolines 3c', 3c" (diastereomers between them), 3a, 3b, and 6; two oxazines 4c' and 4c" (also diastereomers between them); and four pyrrol derivatives 7-10, are analyzed in this paper. Compounds 3b, 3c', 3c", 4c', 4c", 5b, 5c, 6, and 10 were found to be inhibitors of the integrated electron transfer chain (NADH oxidase activity) in beef heart submitochondrial particles (SMP), establishing that all of them except compound 3b and 6 only affected to complex I of the mitochondrial respiratory chain. The most potent product was 5b, with an IC50 of 0.27 mu M, similar to the IC50 values of other known complex I inhibitors. The diastereomeric pairs 1 c'/1c", 3c'/3c", 4c'/4c", and 5c have not been previously described. Chemical characterization, on the basis of spectral data, is also shown.

  DOI：

  10.1021/jf058075f
• 作为产物：
  描述：

  1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione 在 Oxone 、 碳酸氢钠 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 2-heptyl-6,7-dihydro-8(8aH)-hydroxy-3-methyl-4H-pyrrole[2,1-b][1,3]oxazine-4-one
  参考文献：
  名称：

  Novel Inhibitors of the Mitochondrial Respiratory Chain:  Oximes and Pyrrolines Isolated from Penicillium brevicompactum and Synthetic Analogues

  摘要：

  The capacity of inhibition of the mammalian mitochondrial respiratory chain of brevioxime 5a, a natural insecticide compound isolated from Penicillium brevicompactum culture broth, and another 15 analogue compounds, other oximes 5b and 5c; two diastereomeric pyrrolidines 1c' and 1c"; five pyrrolines 3c', 3c" (diastereomers between them), 3a, 3b, and 6; two oxazines 4c' and 4c" (also diastereomers between them); and four pyrrol derivatives 7-10, are analyzed in this paper. Compounds 3b, 3c', 3c", 4c', 4c", 5b, 5c, 6, and 10 were found to be inhibitors of the integrated electron transfer chain (NADH oxidase activity) in beef heart submitochondrial particles (SMP), establishing that all of them except compound 3b and 6 only affected to complex I of the mitochondrial respiratory chain. The most potent product was 5b, with an IC50 of 0.27 mu M, similar to the IC50 values of other known complex I inhibitors. The diastereomeric pairs 1 c'/1c", 3c'/3c", 4c'/4c", and 5c have not been previously described. Chemical characterization, on the basis of spectral data, is also shown.

  DOI：

  10.1021/jf058075f