3a,5-diphenyl-9b-hydroxy-1-methyl-1,2,3,3a,9b-pentahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4-one | 1220887-17-1

• 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,5-diphenyl-9b-hydroxy-1-methyl-1,2,3,3a,9b-pentahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4-one
• CAS: 1220887-17-1
• 化学式: C₂₃H₁₉N₃O₂S
• 分子量: 401.489
• InChiKey: SDOHRSYYXSBCNB-UHFFFAOYSA-N

物化性质

• 熔点：
  241-245 °C(Solvent: Benzene)
• 沸点：
  644.7±65.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 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,5-diphenyl-9b-hydroxy-1-methyl-1,2,3,3a,9b-pentahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4-one 在 溶剂黄146 作用下， 反应 4.0h， 以70%的产率得到1',5-diphenyl-3-methyl-2-thioxospiro[imidazol-4,3'-[3H]indol]-2'(1'H,3H)-one
  参考文献：
  名称：

  Reaction of 3-phenyl-3-aminoquinoline-2,4-diones with isothiocyanates. Facile access to novel spiro-linked 2-thioxoimidazolidine-oxindoles and imidazoline-2-thiones

  摘要：

  3-Phenyl-3-amino-1H,3H-quinoline-2,4-diones (1) react with alkyl or aryl isothiocyanates to give novel 9b-hydroxy-3a-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-ones in high yields. These compounds rearrange in boiling acetic acid or concentrated hydrochloric acid to give novel 5-phenyl-2-thioxospiro[4H-imidazol-4,3'-[3H]indol]-2'(1'H,3H)-ones, 5-hydroxy-5-phenyl-2-thioxospiro [imidazolidine-4,3'-[3H]indol]-2'-ones and (2-methylaminophenyl)-5-phenyl-1H-imidazole-2(3H)-thiones. All compounds were characterized by their (1)H, (13)C, IR and MS data, and in some cases also by (15)N NMR data. The structures and compositions of four compounds were confirmed by single crystal X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.041
• 作为产物：
  描述：

  3-amino-1,3-diphenyl-1H,3H-quinoline-2,4-dione 、 异硫氰酸甲酯 以 氯仿 为溶剂， 以86%的产率得到3a,5-diphenyl-9b-hydroxy-1-methyl-1,2,3,3a,9b-pentahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4-one
  参考文献：
  名称：

  Reaction of 3-phenyl-3-aminoquinoline-2,4-diones with isothiocyanates. Facile access to novel spiro-linked 2-thioxoimidazolidine-oxindoles and imidazoline-2-thiones

  摘要：

  3-Phenyl-3-amino-1H,3H-quinoline-2,4-diones (1) react with alkyl or aryl isothiocyanates to give novel 9b-hydroxy-3a-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-ones in high yields. These compounds rearrange in boiling acetic acid or concentrated hydrochloric acid to give novel 5-phenyl-2-thioxospiro[4H-imidazol-4,3'-[3H]indol]-2'(1'H,3H)-ones, 5-hydroxy-5-phenyl-2-thioxospiro [imidazolidine-4,3'-[3H]indol]-2'-ones and (2-methylaminophenyl)-5-phenyl-1H-imidazole-2(3H)-thiones. All compounds were characterized by their (1)H, (13)C, IR and MS data, and in some cases also by (15)N NMR data. The structures and compositions of four compounds were confirmed by single crystal X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.041