1,3-Dioxolo<4,5-g>furo<3,4-b>quinolin-8(6H)-one | 6720-24-7

• 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: 1,3-Dioxolo<4,5-g>furo<3,4-b>quinolin-8(6H)-one
• 英文别名: 6,7-(methylenedioxy)furo[3,4-b]quinolin-1(3H)-one；6H-[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8-one；2-Hydroxymethyl-6,7-methylenedioxy-3-quinolinecarboxylic acid lactone；5,12,14-Trioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8,10,15-pentaen-6-one
• CAS: 6720-24-7
• 化学式: C₁₂H₇NO₄
• 分子量: 229.192
• InChiKey: SKUOEXFOXANVJY-UHFFFAOYSA-N

物化性质

• 熔点：
  281-282 °C(Solv: ethanol (64-17-5))
• 沸点：
  512.7±50.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-Dioxolo<4,5-g>furo<3,4-b>quinolin-8(6H)-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以78%的产率得到6,7-(methylenedioxy)-4-oxofuro[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  Design and Effective Synthesis of the First 4-Aza-2,3-didehydropodophyllotoxin Rigid Aminologue: A N-Methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone

  摘要：

  [GRPAHICS]The first N1-alkyl-4-amino- 1,2-dihydroquinoline-lactone has been prepared by a five-step sequence in a 51 % overall yield via the corresponding furo[3,4-b]quinolin- 1 (3H)-one. A new practical synthesis of this intermediate was carried out using versatile, commercially available starting materials and constitutes the shortest and highest yielding route. These synthetic pathways could be widened with a view toward the preparation of different substituted derivatives, which could be considered as rigid aminologues of 4-aza-2,3-dide-hydropodophyllotoxins.

  DOI：

  10.1021/jo800166b
• 作为产物：
  描述：

  1-(6-methyl-5-oxy-[1,3]dioxolo[4,5-g]quinolin-7-yl)-ethanone 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 1,3-Dioxolo<4,5-g>furo<3,4-b>quinolin-8(6H)-one
  参考文献：
  名称：

  A new method for the preparation of 2-hydroxymethyl-3-quinolinecarboxylic acid lactone derivatives.

  摘要：

  2-acetoxymethyl-3-acetylquinolines (V, VI) 与氢化钠反应生成 2-hydroxymethyl-3-quinolinecarboxylic acid lactones (IX, X)，推测是乙酰基迁移形成的。另一方面，3-乙酰基-2-苯甲酰氧基甲基喹啉（VIII）与氢化钠反应生成内酯（IX）和苯乙酮，这一事实有力地支持了酰基迁移形成内酯的机理。

  DOI：

  10.1248/cpb.23.2451

文献信息

• Substituted .gamma.-butyrolactones. Part 31. 2,4(3H,5H)-Furandione: heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones
  作者：Diane Grob Schmidt、Paul D. Seemuth、Hans Zimmer

  DOI：10.1021/jo00159a029

  日期：1983.6
• SCHMIDT, D. G.;SEEMUTH, P. D.;ZIMMER, H., J. ORG. CHEM., 1983, 48, N 11, 1914-1916
  作者：SCHMIDT, D. G.、SEEMUTH, P. D.、ZIMMER, H.

  DOI：——

  日期：——
• KURIHARA T.; MICHIDA T.; HIRANO H., CHEM. AND PHARM. BULL. <CPBT-AL>, 1975, 23, NO 10, 2451-2453
  作者：KURIHARA T.、 MICHIDA T.、 HIRANO H.

  DOI：——

  日期：——
• Design and Effective Synthesis of the First 4-Aza-2,3-didehydropodophyllotoxin Rigid Aminologue: A <i>N</i>-Methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone
  作者：Raphaël Labruère、Philippe Helissey、Stéphanie Desbène-Finck、Sylviane Giorgi-Renault

  DOI：10.1021/jo800166b

  日期：2008.5.1

  [GRPAHICS]The first N1-alkyl-4-amino- 1,2-dihydroquinoline-lactone has been prepared by a five-step sequence in a 51 % overall yield via the corresponding furo[3,4-b]quinolin- 1 (3H)-one. A new practical synthesis of this intermediate was carried out using versatile, commercially available starting materials and constitutes the shortest and highest yielding route. These synthetic pathways could be widened with a view toward the preparation of different substituted derivatives, which could be considered as rigid aminologues of 4-aza-2,3-dide-hydropodophyllotoxins.
• A new method for the preparation of 2-hydroxymethyl-3-quinolinecarboxylic acid lactone derivatives.
  作者：TAKUSHI KURIHARA、TAKASHI MICHIDA、HIROSHI HIRANO

  DOI：10.1248/cpb.23.2451

  日期：——

  The reaction of 2-acetoxymethyl-3-acetylquinolines (V, VI) with sodium hydride gave 2-hydroxymethyl-3-quinolinecarboxylic acid lactones (IX, X), presumably formed with the migration of acetyl group. On the other hand, the fact that the reaction of 3-acetyl-2-benzoyloxymethylquinoline (VIII) with sodium hydride gave a lactone (IX) and acetophenone would strongly support for the mechanism of the lactone formation with the acyl migration.

  2-acetoxymethyl-3-acetylquinolines (V, VI) 与氢化钠反应生成 2-hydroxymethyl-3-quinolinecarboxylic acid lactones (IX, X)，推测是乙酰基迁移形成的。另一方面，3-乙酰基-2-苯甲酰氧基甲基喹啉（VIII）与氢化钠反应生成内酯（IX）和苯乙酮，这一事实有力地支持了酰基迁移形成内酯的机理。