4-甲基-6-(1,2,2,4-四甲基-(1,2-二氢喹啉-6-基))-5,6-二氢吡喃-2-醇 | 652992-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 4-甲基-6-(1,2,2,4-四甲基-(1,2-二氢喹啉-6-基))-5,6-二氢吡喃-2-醇
• 英文名称: 4-methyl-6-(1,2,2,4-tetramethyl-(1,2-dihydroquinolin-6-yl))-5,6-dihydropyran-2-ol
• CAS: 652992-12-6
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: XVKGLOHQEDKUGW-UHFFFAOYSA-N

物化性质

• 沸点：
  443.6±45.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-甲基-6-(1,2,2,4-四甲基-(1,2-二氢喹啉-6-基))-5,6-二氢吡喃-2-醇 在 盐酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以87 mg的产率得到(2Z,4E)-3-methyl-5-(1,2,2,4-tetramethyl-(1,2-dihydroquinolin-6-yl))penta-2,4-dienal
  参考文献：
  名称：

  Novel Heteroarotinoids as Potential Antagonists of Mycobacterium bovis BCG

  摘要：

  A series of 15 heteroarotinoids has been prepared and evaluated for activity against Mycobacterium bovis BCG with the thiourea-containing isoxyl (7) (0.5 mug/mL) as the standard. 2,2,4-Trimethyl-2H-chromen-7-yl 4-(methoxycarbonyl)benzoate (8) displayed the most significant activity (2.0-4.0 mug/mL) in terms of the lowest concentration (mug/mL) (MIC, minimum inhibitory concentration) required to produce a 99% reduction in the number of colonies on a plate as compared to that system free of the agent at the same dilution of the culture suspension. Ethyl 4-{[N-(2,2,4,4-tetramethylchroman-6-yl)thiocarbamoyl] amino}benzoate (9) and {[(1E,3Z,5E)-1-aza-4-methyl-6-(1,2,2,4-tetramethyl(1,2-dihydroquinolyl))hexa-1,3,5-trienyl]-amino}aminomethane-1-thione (10) exhibited activity at 5.0-10.0 and 10.0-20.0 mug/mL, respectively, while the other examples had MIC values of 20 mug/mL or greater. The inhibitory ability of 8 may occur via the inhibition of mycolic acid synthesis in a like manner as found with 7, but this requires further study. The heteroarotinoids are the first examples to exhibit inhibitory ability against the growth of Mycobacterium bovis BCB.

  DOI：

  10.1021/jm0303453
• 作为产物：
  描述：

  1,2,2,4-tetramethyl-1,2-dihydroquinoline 在 二异丁基氢化铝 、 lithium diisopropyl amide 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 26.33h， 生成 4-甲基-6-(1,2,2,4-四甲基-(1,2-二氢喹啉-6-基))-5,6-二氢吡喃-2-醇
  参考文献：
  名称：

  Novel Heteroarotinoids as Potential Antagonists of Mycobacterium bovis BCG

  摘要：

  A series of 15 heteroarotinoids has been prepared and evaluated for activity against Mycobacterium bovis BCG with the thiourea-containing isoxyl (7) (0.5 mug/mL) as the standard. 2,2,4-Trimethyl-2H-chromen-7-yl 4-(methoxycarbonyl)benzoate (8) displayed the most significant activity (2.0-4.0 mug/mL) in terms of the lowest concentration (mug/mL) (MIC, minimum inhibitory concentration) required to produce a 99% reduction in the number of colonies on a plate as compared to that system free of the agent at the same dilution of the culture suspension. Ethyl 4-{[N-(2,2,4,4-tetramethylchroman-6-yl)thiocarbamoyl] amino}benzoate (9) and {[(1E,3Z,5E)-1-aza-4-methyl-6-(1,2,2,4-tetramethyl(1,2-dihydroquinolyl))hexa-1,3,5-trienyl]-amino}aminomethane-1-thione (10) exhibited activity at 5.0-10.0 and 10.0-20.0 mug/mL, respectively, while the other examples had MIC values of 20 mug/mL or greater. The inhibitory ability of 8 may occur via the inhibition of mycolic acid synthesis in a like manner as found with 7, but this requires further study. The heteroarotinoids are the first examples to exhibit inhibitory ability against the growth of Mycobacterium bovis BCB.

  DOI：

  10.1021/jm0303453