3-Acetyl-1-butyl-4-hydroxy-1H-quinolin-2-one | 161185-41-7

• 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
• 英文名称: 3-Acetyl-1-butyl-4-hydroxy-1H-quinolin-2-one
• 英文别名: 3-acetyl-1-butyl-4-hydroxy-2(1H)-quinolinone；3-acetyl-1-butyl-4-hydroxyquinolin-2-one
• CAS: 161185-41-7
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: LRWTVVXLKGMEIC-UHFFFAOYSA-N

物化性质

• 溶解度：
  26.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Acetyl-1-butyl-4-hydroxy-1H-quinolin-2-one 在 硫酸 作用下， 反应 0.08h， 以66%的产率得到1-butyl-4-hydroxy-2(1H)-quinolone
  参考文献：
  名称：

  Syntheses of 3-Acyl-4-hydroxy-2(1H)quinolones

  摘要：

  3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyrano[3,2-c]quinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3. Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)quinolones 8. Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.

  DOI：

  10.1002/prac.19943360707
• 作为产物：
  描述：

  6-butyl-3H-pyrano[3,2-c]quinoline-2,4,5(6H)-trione 在 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 1.5h， 以96%的产率得到3-Acetyl-1-butyl-4-hydroxy-1H-quinolin-2-one
  参考文献：
  名称：

  Syntheses of 3-Acyl-4-hydroxy-2(1H)quinolones

  摘要：

  3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyrano[3,2-c]quinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3. Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)quinolones 8. Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.

  DOI：

  10.1002/prac.19943360707

文献信息

• Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX
  作者：Mohamed Abass、Bayaumy B. Mostafa

  DOI：10.1016/j.bmc.2005.06.038

  日期：2005.11

  series of 10 3-(hetarylaminomethylene)quinolinediones, 12 3-(substituted aminopropenoyl)-4-hydroxyquinolinones, and 10 3-(substituted aminomethylene-5-oxo-pyrazolinyl)-4-hydroxyquinolinones were synthesized as novel enaminones derived from 3-(un)substituted 4-hydroxyquinolin-2(1H)-ones in 72-94% yields and assayed for their molluscicidal activities against Biomphalaria alexandrina and Lymnaea natalensis

  合成了一系列的10个3-（杂芳基氨基亚甲基）喹啉二酮，12个3-（取代的氨基丙烯酰基）-4-羟基喹啉酮和10个3-（取代的氨基亚甲基-5-氧代吡唑啉基）-4-羟基喹啉酮，它们是由3-衍生而来的新型烯胺酮。 （un）取代的4-羟基喹啉-2（1H）-酮的产率为72-94％，并测定了它们对Biomphalaria alexandrina和Lymnaea natalensis蜗牛的杀软体动物活性。一些测试的烯胺酮具有很高的杀软体动物活性（LC（50）20ppm）。新化合物显示出了对亚历山大藻的卵孵化率，蜗牛的感染率和有效期更强的效力。此外，这些衍生物在减少接触时间的情况下显示出对曼氏血吸虫的水acid和尾c均具有潜在的杀幼虫作用（100％死亡率）。
• Syntheses of 3-Acyl-4-hydroxy-2(1H)quinolones
  作者：Thomas Kappe、Rudolf Aigner、Peter Hohengassner、Wolfgang Stadlbauer

  DOI：10.1002/prac.19943360707

  日期：——

  3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyrano[3,2-c]quinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3. Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)quinolones 8. Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.