3,4-二氯-1-甲基喹啉-2-酮 | 110254-66-5

• 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
• 中文名称: 3,4-二氯-1-甲基喹啉-2-酮
• 英文名称: 3,4-dichloro-1-methylquinolin-2(1H)-one
• 英文别名: 3,4-dichloro-1-methyl-2(1H)-quinolone；3,4-Dichlor-1-methyl-2(1H)-chinolon；2(1H)-Quinolinone, 3,4-dichloro-1-methyl-；3,4-dichloro-1-methylquinolin-2-one
• CAS: 110254-66-5
• 化学式: C₁₀H₇Cl₂NO
• 分子量: 228.078
• InChiKey: ZQOBVFQRVGHVRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-二氯-1-甲基喹啉-2-酮 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以68.2%的产率得到4-Azido-3-chlor-1-methyl-2(1H)-chinolon
  参考文献：
  名称：

  Methoden zur Darstellung von 4-Azido-2(1H)-chinolonen

  摘要：

  DOI：

  10.1007/bf00810876
• 作为产物：
  描述：

  3-diazo-1-methylquinoline-2,4(1H,3H)-dione 在 tris(triphenylphosphine)ruthenium(II) chloride 、 草酰氯 作用下， 反应 5.0h， 以74%的产率得到3,4-二氯-1-甲基喹啉-2-酮
  参考文献：
  名称：

  钌（II）催化的重氮二羰基化合物制备各种α，β-和β，β-二卤代烯酮的方案

  摘要：

  AbstractEfficient one‐step syntheses of α,β‐ and β,β‐dihaloenones were achieved by ruthenium(II)‐catalyzed reactions between cyclic or acyclic diazodicarbonyl compounds and oxalyl chloride or oxalyl bromide in moderate to good yields. This methodology offers several significant advantages, which include ease of handling, mild reaction conditions, one‐step reaction, and the use of an effective and non‐toxic catalyst. The synthesized compounds were further transformed into highly functionalized novel molecules bearing aromatic rings on the enone moiety using the Suzuki reaction.magnified image

  DOI：

  10.1002/adsc.201400348

文献信息

• Synthesis of quinolin-4-yl substituted malonates, cyanoacetates, acetoacetates and related compounds
  作者：Wolfgang Stadlbauer、Anna E. Täubl、Hoai V. Dang、Claudia Reidlinger、Klaus Zangger

  DOI：10.1002/jhet.5570430118

  日期：2006.1

  CH-acidic compounds such as malonates 2a,b, ethyl cyanoacetate (2c), malononitrile (2d), ethyl acetoacetate (2e), acetylacetone (2f) or dimedone (2g) under mild conditions and good yields to quinolin-4-yl substituted derivatives 3-8 and 11. With 3-phenylsulfonylquinolones 1i-k a redox reaction to 2-hydroxy-2-quinolin-4-yl-malonates 9 was observed. Amination of 3-nitroquinolinyl malonate 3f leads to

  4-氯或4-甲苯氧基喹啉1和10与CH酸性化合物反应，例如丙二酸酯2a，b，氰基乙酸乙酯（2c），丙二腈（2d），乙酰乙酸乙酯（2e），乙酰丙酮（2f）或二甲基酮（2g）在温和的条件下，对喹啉-4-基取代的衍生物3-8和11具有良好的收率。用3-苯基磺酰基喹诺酮类化合物1i-k，观察到对2-羟基-2-喹啉-4-基丙二酸酯9的氧化还原反应。3-硝基喹啉基丙二酸酯3f的胺化反应生成马洛酯酰胺13和14。
• Ruthenium(II)-Catalyzed Protocol for Preparation of Diverse α,β- and β,β-Dihaloenones from Diazodicarbonyls
  作者：Krishna Bahadur Somai Magar、Yong Rok Lee

  DOI：10.1002/adsc.201400348

  日期：2014.11.3

  AbstractEfficient one‐step syntheses of α,β‐ and β,β‐dihaloenones were achieved by ruthenium(II)‐catalyzed reactions between cyclic or acyclic diazodicarbonyl compounds and oxalyl chloride or oxalyl bromide in moderate to good yields. This methodology offers several significant advantages, which include ease of handling, mild reaction conditions, one‐step reaction, and the use of an effective and non‐toxic catalyst. The synthesized compounds were further transformed into highly functionalized novel molecules bearing aromatic rings on the enone moiety using the Suzuki reaction.magnified image
• MALLE, ERNST;STADLBAUER, WOLFGANG;OSTERMANN, GUNTER;HOFMANN, BARBARA;LEIS+, EUR. J. MED. CHEM., 25,(1990) N, C. 137-142
  作者：MALLE, ERNST、STADLBAUER, WOLFGANG、OSTERMANN, GUNTER、HOFMANN, BARBARA、LEIS+

  DOI：——

  日期：——
• STADLBAUER W., MONATSH. CHEM., 117,(1986) N 11, 1305-1323
  作者：STADLBAUER W.

  DOI：——

  日期：——
• Methoden zur Darstellung von 4-Azido-2(1H)-chinolonen
  作者：Wolfgang Stadlbauer

  DOI：10.1007/bf00810876

  日期：1986.11