5-{[(2-methylphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione | 25253-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-{[(2-methylphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 2,2-Dimethyl-5-{[(2-methylphenyl)amino]methylidene}-1,3-dioxane-4,6-dione；2,2-dimethyl-5-[(2-methylanilino)methylidene]-1,3-dioxane-4,6-dione
• CAS: 25253-09-2
• 化学式: C₁₄H₁₅NO₄
• mdl: MFCD02936588
• 分子量: 261.277
• InChiKey: SVLVTOKDVXFORE-UHFFFAOYSA-N

物化性质

• 沸点：
  457.7±45.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-{[(2-methylphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione 反应 2.0h， 以84%的产率得到4-羟基-8-甲基喹啉
  参考文献：
  名称：

  一种新型的离子液体介导的4（1 H）-喹诺酮，5 H-噻唑并[3,2- a ]嘧啶-5-酮和4 H-嘧啶并[2,1- b ]苯并噻唑-4-酮的合成

  摘要：

  一种新的，方便的，环境友好的两步合成4（1 H）-喹诺酮，5 H-噻唑并[3,2- a ]嘧啶-5-酮和4 H-嘧啶并[2,1- b ]苯并噻唑-通过先在中等温度下将取代的芳基胺/ 2-氨基噻唑/ 2-氨基苯并噻唑与Meldrum的酸和原甲酸三甲酯在1-丁基-3-甲基咪唑鎓溴化物中在中等温度下缩合，得到5-{（取代的芳基/ 4-甲基噻唑基/取代的苯并噻唑基）亚甲基} -2，2-二甲基-1，3-二恶烷-4，6-二酮。在中等温度下在1-丁基-3-甲基四氟硼酸酯/三氟甲磺酸酯中环化后得到的化合物以优异的收率得到标题化合物。

  DOI：

  10.1016/j.tetlet.2011.12.024
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-{[(2-methylphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

  摘要：

  A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.037

文献信息

• Direct C-3-Alkenylation of Quinolones via Palladium-Catalyzed CH Functionalization
  作者：Mingzong Li、Liangxi Li、Haibo Ge

  DOI：10.1002/adsc.201000364

  日期：2010.10.4

  An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed CH functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.

  据报道，钯负载量为1％时，钯催化的CH官能化使喹诺酮类化合物的C-3-烯基化程度达到前所未有的水平。该方法为生产各种新的喹诺酮衍生物提供了有效的途径。
• ——
  作者：D. Zicane、I. Ravina、Z. Tetere、I. Rijkure、M. Petrova、U. Kalejs

  DOI：10.1023/a:1020641922707

  日期：——
• Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities
  作者：Peter B. Madrid、John Sherrill、Ally P. Liou、Jennifer L. Weisman、Joseph L. DeRisi、R. Kiplin Guy

  DOI：10.1016/j.bmcl.2004.12.037

  日期：2005.2

  A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2. (C) 2004 Elsevier Ltd. All rights reserved.
• A novel ionic liquid mediated synthesis of 4(1H)-quinolones, 5H-thiazolo[3,2-a]pyrimidin-5-one and 4H-pyrimido[2,1-b]benzothiazol-4-ones
  作者：Ashok K. Yadav、Gopi Ram Sharma、Pankaj Dhakad、Tripti Yadav

  DOI：10.1016/j.tetlet.2011.12.024

  日期：2012.2

  A new, convenient, environmentally benign two-step synthesis of 4(1H)-quinolones, 5H-thiazolo[3,2-a]pyrimidin-5-one and 4H-pyrimido[2,1-b]benzothiazol-4-ones have been developed by first condensing substituted arylamine/2-aminothiazole/2-aminobenzenethiazole with Meldrum’s acid and trimethylorthoformate in 1-butyl-3-methylimidazolium bromide at a moderate temperature to afford 5-(substituted aryl

  一种新的，方便的，环境友好的两步合成4（1 H）-喹诺酮，5 H-噻唑并[3,2- a ]嘧啶-5-酮和4 H-嘧啶并[2,1- b ]苯并噻唑-通过先在中等温度下将取代的芳基胺/ 2-氨基噻唑/ 2-氨基苯并噻唑与Meldrum的酸和原甲酸三甲酯在1-丁基-3-甲基咪唑鎓溴化物中在中等温度下缩合，得到5-（取代的芳基/ 4-甲基噻唑基/取代的苯并噻唑基）亚甲基} -2，2-二甲基-1，3-二恶烷-4，6-二酮。在中等温度下在1-丁基-3-甲基四氟硼酸酯/三氟甲磺酸酯中环化后得到的化合物以优异的收率得到标题化合物。