3-benzylamino-3-butylquinoline-2,4-(1H,3H)-dione | 477949-97-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-benzylamino-3-butylquinoline-2,4-(1H,3H)-dione
• 英文别名: 3-benzylamino-3-butyl-1H,3H-quinoline-2,4-dione；2,4(1H,3H)-Quinolinedione, 3-butyl-3-[(phenylmethyl)amino]-；3-(benzylamino)-3-butyl-1H-quinoline-2,4-dione
• CAS: 477949-97-6
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: VDDFEIIEOCAZSU-UHFFFAOYSA-N

物化性质

• 沸点：
  523.2±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzylamino-3-butylquinoline-2,4-(1H,3H)-dione 在 phosphorus pentoxide 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 15.17h， 生成 3-benzyl-3a-butyl-3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-dione
  参考文献：
  名称：

  3-氨基喹啉-2,4-二酮与硝基脲的反应。合成新型3-ureidoquinoline-2,4-diones和咪唑并[4,5 - c ] quinoline-2,4- diones的合成途径

  摘要：

  1-未取代的3-烷基/芳基-3-氨基-1 H，3 H-喹啉-2,4-二酮在沸腾的乙酸中与1-取代的和1,1-二取代的脲反应，生成2,6-二氢-咪唑并[1,5 - c ]喹唑啉-3,5-二酮。相比之下，这些胺与硝基脲在二恶烷中的反应提供了新型的3-烷基/芳基-3-脲基-1 H，3 H-喹啉-2,4-二酮或9b-羟基-3a-烷基/芳基-3， 3a，5,9b-四氢-1 H-咪唑并[4,5 - c ]喹啉-2,4-二酮，可以平稳地脱水成3a-烷基/芳基-3,3a-二氢-5 H-咪唑并[ 4,5 - c ]喹啉-2,4-二酮。所有这三种类型的产品都可以转化为2,6-二氢咪唑[1,5- c通过在乙酸中回流得到]喹唑啉-3,5-二酮。

  DOI：

  10.1016/j.tet.2004.07.106
• 作为产物：
  描述：

  3-butyl-4-hydroxyquinolin-2(1H)-one 在 磺酰氯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成 3-benzylamino-3-butylquinoline-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Syntheses of 3-Aminoquinoline- 2,4(1H,3H)-diones

  摘要：

  DOI：

  10.3987/com-02-9522

文献信息

• Reaction of 3-aminoquinoline-2,4-diones with isocyanates. Synthesis of novel 3-(3′-alkyl/arylureido)quinoline-2,4-diones and their cyclic carbinolamide isomers
  作者：Antonín Klásek、Ignác Hoza、Antonín Lyčka、Michal Holčapek

  DOI：10.1002/jhet.5570430132

  日期：2006.1

  3-Alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with alkyl/aryl isocyanates to give novel 3-alkyl/aryl-3-ureido-1H,3H-quinoline-2,4-diones or 3a-alkyl/aryl-9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2,4-diones. In some cases, a mixture of both products was obtained and separated by fractional crystallization. All compounds were characterized by their 1H, 13C, ir and ms data and

  3-烷基/芳基-3-氨基-1 H，3 H-喹啉-2,4-二酮与烷基/芳基异氰酸酯反应生成新的3-烷基/芳基-3-脲基-1 H，3 H-喹啉- 2,4-二酮或3a-烷基/芳基-9b-羟基-3,3a，5,9b-四氢-1 H-咪唑并[4,5 - c ]喹啉-2,4-二酮。在某些情况下，会获得两种产物的混合物，并通过分步结晶进行分离。所有化合物均以1 H，13 C，ir和ms数据为特征，其中一些还以15 N nmr数据为特征。
• Reaction of 3-aminoquinoline-2,4-diones with isothiocyanic acid—an easy pathway to thioxo derivatives of imidazo[1,5-c]quinazolin-5-ones and imidazo[4,5-c]quinolin-4-ones
  作者：Vladimír Mrkvička、Antonín Lyčka、Ondřej Rudolf、Antonín Klásek

  DOI：10.1016/j.tet.2010.08.056

  日期：2010.10

  potassium thiocyanate in boiling acetic acid to give novel 2,3-dihydro-3-thioxoimidazo[1,5-c]quinazolin-5(6H)-ones in high yields. However, if the starting compounds are substituted with a benzyl group at position 3, a C-debenzylation proceeds to give 2,3-dihydro-2-thioxo-1H-imidazo[4,5-c]quinolin-4(5H)-ones. According to a proposed reaction mechanism, a molecular rearrangement of the primarily formed mono-substituted

  3-Amino-1 H，3 H -quinoline-2,4-diones与硫脲或硫氰酸钾在沸腾的乙酸中反应，生成新的2,3-二氢-3-thioxoimidazo [1,5- c ] quinazolin -5（高产率的6 H）-一。但是，如果起始化合物在位置3处被苄基取代，则会进行C-脱苄基作用，得到2,3-二氢-2-硫代-1 H-咪唑并[4,5- c ]喹啉-4（5 H）-那些。根据提出的反应机理，发生了最初形成的单取代的硫脲的分子重排。所有化合物的特征在于1 H，13 C和15N NMR和IR光谱以及质谱法。
• Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates
  作者：Zdenka Prucková、Antonín Klásek、Antonín Lyčka、Ivan Mikšík、Aleš Růžička

  DOI：10.1016/j.tet.2009.09.048

  日期：2009.11

  3-Alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with alkyl/aryl isothiocyanates to give 3a-alkyl/aryl-1,2,3,3a-tetrahydro-9b-hydroxy-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-ones in high yields. These compounds rearrange in boiling acetic acid or concd hydrochloric acid to give novel 4-(2-aminophenyl)-1H-imidazole-2(3H)-thiones, 1,3-bis(2-(2,3-dihydro-2-thioxo-1H-imidazol-5-yl)phenyl)ureas and minor N-(2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phenyl)acetamides. In the presence of ethanol, the starting compounds rearrange in boiling acetic acid to give ethyl 2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phenylcarbamates. All compounds were characterized by their H-1, C-13, IR and MS spectra and some of them also by N-15 NMR data. The structures of two compounds were supported by single-crystal X-ray diffraction. (C) 2009 Elsevier Ltd. All rights reserved.
• Unprecedented reactivity of 3-amino-1H,3H-quinoline-2,4-diones with urea: an efficient synthesis of 2,6-dihydro-imidazo[1,5-c]quinazoline-3,5-diones
  作者：Antonı́n Klásek、Kamil Kořistek、Antonı́n Lyčka、Michal Holčapek

  DOI：10.1016/s0040-4020(03)00028-0

  日期：2003.2

  Substituted 3-amino-1H,3H-quinoline-2,4-diones react with urea in acetic acid to, give novel 2,6-dihydro-imidazo[1,5-c]-quinazoline-3,5-diones in high yields. The same compounds were obtained, albeit with small yields, from 3-chloro-1H,3H-quinoline-2,4-diones and urea. In the proposed reaction mechanism, a molecular rearrangement of the primarily formed mono-substituted urea takes place. The prepared 2,6-dihydro-imidazo[1,5-c]-quinazoline-3,5-diones were characterized by their H-1, C-13, N-15 NMR and IR spectra and atmospheric pressure chemical ionisation mass spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Syntheses of 3-Aminoquinoline- 2,4(1H,3H)-diones
  作者：Antonín Klásek、Stanislav Kafka、Jirí Polis、Janez Kosmrlj

  DOI：10.3987/com-02-9522

  日期：——