3,3a-dibutyl-1,5-dimethyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydroimidazo[4,5-c]quinolin-4-one | 1172630-86-2

• 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: 3,3a-dibutyl-1,5-dimethyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydroimidazo[4,5-c]quinolin-4-one
• 英文别名: 3,3a-Dibutyl-9b-hydroxy-1,5-dimethyl-2-sulfanylideneimidazo[4,5-c]quinolin-4-one；3,3a-dibutyl-9b-hydroxy-1,5-dimethyl-2-sulfanylideneimidazo[4,5-c]quinolin-4-one
• CAS: 1172630-86-2
• 化学式: C₂₀H₂₉N₃O₂S
• 分子量: 375.535
• InChiKey: WETLKRDWLPZZID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3a-dibutyl-1,5-dimethyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydroimidazo[4,5-c]quinolin-4-one 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以72%的产率得到(5E)-1-butyl-5-butylidene-1',3-dimethyl-2-thioxospiro[imidazolidine-4,3'-indol]-2'(1'H)-one
  参考文献：
  名称：

  Reaction of 1-substituted 3-aminoquinoline-2,4-diones with isothiocyanates. An easy pathway to generate novel 2-thioxo-1′H-spiro[imidazoline-5,3′-indole]-2,2′-diones

  摘要：

  3-Butyl-3-amino-1H,3H-quinoline-2.4-diones react with isothiocyanates to give novel 3a-butyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydro-imidazo[4,5-c]quinolin-2-ones in high yields. These compounds rearrange in boiling acetic acid or concd hydrochloric acid to give (E)- and/or (Z)-4-butylidene-2-thioxo-1'H-spiro[imidazoline-5,3'-indole]-2,2'-diones. All compounds were characterized by their (1)H, (13)C, IR and MS spectra, and some of them also by (15)N NMR. The structure of one compound was investigated by single-crystal X-ray diffraction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.009
• 作为产物：
  描述：

  异硫氰酸甲酯 、 3-丁基-3-(丁基氨基)-1-甲基喹啉-2,4-二酮 以 氯仿 为溶剂， 以58%的产率得到3,3a-dibutyl-1,5-dimethyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydroimidazo[4,5-c]quinolin-4-one
  参考文献：
  名称：

  Reaction of 1-substituted 3-aminoquinoline-2,4-diones with isothiocyanates. An easy pathway to generate novel 2-thioxo-1′H-spiro[imidazoline-5,3′-indole]-2,2′-diones

  摘要：

  3-Butyl-3-amino-1H,3H-quinoline-2.4-diones react with isothiocyanates to give novel 3a-butyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydro-imidazo[4,5-c]quinolin-2-ones in high yields. These compounds rearrange in boiling acetic acid or concd hydrochloric acid to give (E)- and/or (Z)-4-butylidene-2-thioxo-1'H-spiro[imidazoline-5,3'-indole]-2,2'-diones. All compounds were characterized by their (1)H, (13)C, IR and MS spectra, and some of them also by (15)N NMR. The structure of one compound was investigated by single-crystal X-ray diffraction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.009

文献信息

• Reaction of 1-substituted 3-aminoquinoline-2,4-diones with isothiocyanates. An easy pathway to generate novel 2-thioxo-1′H-spiro[imidazoline-5,3′-indole]-2,2′-diones
  作者：Antonín Klásek、Vladimír Mrkvička、Antonín Lyčka、Ivan Mikšík、Aleš Růžička

  DOI：10.1016/j.tet.2009.04.009

  日期：2009.6

  3-Butyl-3-amino-1H,3H-quinoline-2.4-diones react with isothiocyanates to give novel 3a-butyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydro-imidazo[4,5-c]quinolin-2-ones in high yields. These compounds rearrange in boiling acetic acid or concd hydrochloric acid to give (E)- and/or (Z)-4-butylidene-2-thioxo-1'H-spiro[imidazoline-5,3'-indole]-2,2'-diones. All compounds were characterized by their (1)H, (13)C, IR and MS spectra, and some of them also by (15)N NMR. The structure of one compound was investigated by single-crystal X-ray diffraction. (C) 2009 Elsevier Ltd. All rights reserved.