3a-butyl-9b-hydroxy-3-methyl-1-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-one | 1198770-96-5

• 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: 3a-butyl-9b-hydroxy-3-methyl-1-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-one
• CAS: 1198770-96-5
• 化学式: C₂₁H₂₃N₃O₂S
• 分子量: 381.499
• InChiKey: DBLOERKCNKKODO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.81
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3a-butyl-9b-hydroxy-3-methyl-1-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-one 在 盐酸 、 吡啶 作用下， 以 水 为溶剂， 反应 2.5h， 以76%的产率得到4-(2-aminophenyl)-5-butyl-1-methyl-3-phenyl-1H-imidazole-2(3H)-thione
  参考文献：
  名称：

  Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.09.048
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 3-butyl-3-methylamino-1H,3H-quinoline-2,4-dione 以 氯仿 为溶剂， 以97%的产率得到3a-butyl-9b-hydroxy-3-methyl-1-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-one
  参考文献：
  名称：

  Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.09.048