3,3-Diallyl-1,2,3,4-tetrahydroquinolin-2,4-dione | 42997-27-3

• 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: 3,3-Diallyl-1,2,3,4-tetrahydroquinolin-2,4-dione
• 英文别名: 3,3-Diallyl-1,2,3,4-tetrahydro-2,4-chinolindion；3,3-diallylquinoline-2,4(1H,3H)-dione；3,3-diallyl-1H-quinoline-2,4-dione；3,3-diallyl-1H-quinoline-2,4-dione；3,3-bis(prop-2-enyl)-1H-quinoline-2,4-dione
• CAS: 42997-27-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: MAOAHKYDWBAMSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-Diallyl-1,2,3,4-tetrahydroquinolin-2,4-dione 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 2,6-dimethyl-2,3,5,6-tetrahydro-1'H-spiro[pyran-4,3'-quinoline]-2',4'-dione
  参考文献：
  名称：

  Kappe,T. et al., Chemische Berichte, 1973, vol. 106, p. 1927 - 1942

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-喹啉二醇 、 3-溴丙烯 在 potassium carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以61%的产率得到3,3-Diallyl-1,2,3,4-tetrahydroquinolin-2,4-dione
  参考文献：
  名称：

  2,2,2-三氟乙醇促进获得对称的3,3-二取代喹啉-2,4-二酮

  摘要：

  通过2,2,2-三氟乙醇作为反应溶剂的空前使用，通过4-羟基-苯酚的反应，以中等至极好的收率和高区域选择性提供了一种方便且便捷的途径，可对称地获得3,3-二取代的喹啉-2,4-二酮。在K 2 CO 3存在下，具有亲电试剂的2-喹诺酮类化合物，如甲基碘，以及苄基和烯丙基溴。需要氧化银（I）以增加甲基化的产率。

  DOI：

  10.1016/j.jfluchem.2020.109520

文献信息

• Efficient chemoselective alkylation of quinoline 2,4-diol derivatives in water
  作者：Nafees Ahmed、Keyur G. Brahmbhatt、Inder P. Singh、Kamlesh K. Bhutani

  DOI：10.1002/jhet.364

  日期：2011.1

  Synthesis of various C‐3‐dialkyl derivatives of quinoline 2,4‐diol was achieved by condensation of aniline or substituted anilines with diethyl malonate, followed by chemoselective alkylation at C‐3 in water. The higher yields, easy work up and environmental compatible conditions are the main aspects of our method. J. Heterocyclic Chem., 2011.

  苯胺或取代的苯胺与丙二酸二乙酯的缩合反应，然后在水中的C-3进行化学选择性烷基化，从而实现喹啉2,4-二醇的各种C-3-二烷基衍生物的合成。较高的收率，易于加工和与环境兼容的条件是我们方法的主要方面。J.杂环化​​学.2011。
• Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols
  作者：Nafees Ahmed、Keyur G. Brahmbhatt、Sudeep Sabde、Debashis Mitra、Inder Pal Singh、Kamlesh K. Bhutani

  DOI：10.1016/j.bmc.2010.03.015

  日期：2010.4

  Naturally occurring quinolone alkaloids, buchapine (1) and compound 2 were synthesized as reported in literature and evaluated for anti-HIV potential in human CD4+ T cell line CEM-GFP, infected with HIV-1(NL4.3) virus by p24 antigen capture ELISA assay. The compounds 1 and 2 showed potent inhibitory activity with IC50 value of 2.99 and 3.80 mu M, respectively. Further, 45 alkylated derivatives of quinoline 2,4-diol were synthesized and tested for anti-HIV potential in human CD4+ T cell line CEM-GFP. Among these, 13 derivatives have shown more than 60% inhibition. We have identified three most potent inhibitors 6, 9 and 23; compound 6 was found to be more potent than lead molecule 1 with IC50 value of 2.35 mu M and had better therapeutic index (26.64) as compared to AZT (23.07). Five derivatives 7, 19a, 19d, 21 and 24 have displayed good noticeable anti-HIV activity. All active compounds showed higher CC50 values which indicate that they have better therapeutic indices. (C) 2010 Elsevier Ltd. All rights reserved.
• Shobana, N.; Shanmugam, P., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 1264 - 1265
  作者：Shobana, N.、Shanmugam, P.

  DOI：——

  日期：——
• 2,2,2-trifluoroethanol-promoted access to symmetrically 3,3-disubstituted quinoline-2,4-diones
  作者：Marcel Manke Selvero、Gabriela N. Ledesma、Ulrich Abram、Ernesto Schulz-Lang、Ademir Farias Morel、Enrique L. Larghi

  DOI：10.1016/j.jfluchem.2020.109520

  日期：2020.6

  unprecedented use of 2,2,2-trifluoroethanol as reaction solvent provided a facile and convenient access to symmetrically 3,3-disubstitued quinoline-2,4-diones in moderate to excellent yields and high regioselectivity, by reaction of 4-hydroxy-2-quinolones with electrophiles like methyl iodide, as well as benzyl and allyl bromides in the presence of K2CO3. Silver (I) oxide is required to increase the yield of

  通过2,2,2-三氟乙醇作为反应溶剂的空前使用，通过4-羟基-苯酚的反应，以中等至极好的收率和高区域选择性提供了一种方便且便捷的途径，可对称地获得3,3-二取代的喹啉-2,4-二酮。在K 2 CO 3存在下，具有亲电试剂的2-喹诺酮类化合物，如甲基碘，以及苄基和烯丙基溴。需要氧化银（I）以增加甲基化的产率。
• Kappe,T. et al., Chemische Berichte, 1973, vol. 106, p. 1927 - 1942
  作者：Kappe,T. et al.

  DOI：——

  日期：——