4-chloro-2-hydrazinylbenzo[h]quinoline | 1619258-88-6

• 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: 4-chloro-2-hydrazinylbenzo[h]quinoline
• 英文别名: (4-Chlorobenzo[h]quinolin-2-yl)hydrazine；(4-chlorobenzo[h]quinolin-2-yl)hydrazine
• CAS: 1619258-88-6
• 化学式: C₁₃H₁₀ClN₃
• 分子量: 243.695
• InChiKey: ONZFDXDDIJIAQS-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  428.6±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-2-hydrazinylbenzo[h]quinoline 、 乙酰丙酮 在 indium(III) chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 以87%的产率得到4-chloro-2-(3,5-dimethyl-1H-pyrazol-1-yl)benzo[h]quinoline
  参考文献：
  名称：

  InCl₃-Promoted Synthesis of Pyrazolyl-Substituted Quinolines in Green Media

  摘要：

  A series of regioisomers of pyrazolyl-substituted quinolines has been synthesized through the simple condensation reaction between hydrazinylquinolines with aliphatic 1,3-diketones with InCl3 as a catalyst under microwave irradiation. This method produces pure products in good yield in a rapid manner compared to conventional procedures and withneat reaction condition. The approach has the advantages of operational simplicity and increased safety for a shortened synthesis of pyrazolyl-substituted quinolines.

  DOI：

  10.1080/00397911.2015.1041608
• 作为产物：
  描述：

  2,4-dichlorobenzo[h]quinoline 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以69%的产率得到2-chloro-4-hydrazinylbenzo[h]quinoline
  参考文献：
  名称：

  2,4-二氯喹啉的高度区域选择性C4-肼基化：通过肼基喹啉方便地合成氨基喹啉取代的吡咯烷-2,5-二酮

  摘要：

  通过2,4-二氯喹啉与水合肼的S N Ar反应合成了一类新的肼基喹啉区域异构体。反应在二氯喹啉的C 4位置而不是C 2位置处以具有高区域选择性的单取代产物终止。随后在伊顿试剂的存在下将肼基喹啉转化为氨基喹啉取代的吡咯烷-2，5-二酮。

  DOI：

  10.1016/j.tetlet.2014.05.132

文献信息

• Synthesis, DNA binding and cytotoxic evaluation of aminoquinoline scaffolds
  作者：GOPAL SENTHIL KUMAR、MOHAMED ASHRAF ALI、TAN SOO CHOON、KARNAM JAYARAMPILLAI RAJENDRA PRASAD

  DOI：10.1007/s12039-015-1025-5

  日期：2016.3

  effortless synthetic route has been developed for the synthesis of a new class of aminoquinoline substituted isoindolin-1,3-diones from regio-isomerical hydrazinylquinolines with phthalic anhydride in presence of Eaton’s reagent. DNA binding studies of selected isomeric compounds showed interaction with DNA via intercalation mode with higher binding affinity of 4-substituted quinolines rather than 2-substituted

  在伊顿试剂的存在下，由区域异构的肼基喹啉与邻苯二甲酸酐合成毫微的新型氨基喹啉取代的异吲哚啉-1,3-二酮类化合物已被轻松开发。所选异构体化合物的DNA结合研究表明，该化合物通过嵌入模式与DNA相互作用，并具有更高的4取代喹啉而不是2取代喹啉的结合亲和力。此外，针对所有三种人类癌细胞系筛选了所有化合物的细胞毒活性，其中化合物2c超出了针对CCRF-CEM细胞系的标准阿霉素。 已经探索了使用伊顿试剂作为催化剂合成氨基喹啉取代的异吲哚啉-1,3-二酮的简便方法。DNA结合和体外细胞毒性研究揭示了氨基喹啉支架在癌症治疗中的重要性。
• InCl₃-Promoted Synthesis of Pyrazolyl-Substituted Quinolines in Green Media
  作者：Gopal Senthil Kumar、Werner Kaminsky、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1080/00397911.2015.1041608

  日期：2015.8.3

  A series of regioisomers of pyrazolyl-substituted quinolines has been synthesized through the simple condensation reaction between hydrazinylquinolines with aliphatic 1,3-diketones with InCl3 as a catalyst under microwave irradiation. This method produces pure products in good yield in a rapid manner compared to conventional procedures and withneat reaction condition. The approach has the advantages of operational simplicity and increased safety for a shortened synthesis of pyrazolyl-substituted quinolines.
• Highly regioselective C4-hydrazinylation of 2,4-dichloroquinolines: expedient synthesis of aminoquinoline substituted pyrrolidin-2,5-diones via hydrazinylquinolines
  作者：Gopal Senthil Kumar、Matthias Zeller、Rajesh Ghanshyam Gonnade、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1016/j.tetlet.2014.05.132

  日期：2014.7

  A new class of hydrazinylquinoline regio-isomers has been synthesized through SNAr reaction of 2,4-dichloroquinolines with hydrazine hydrate. The reaction stops at the mono-substitution product with high regioselectivity at the C4 rather than C2 position of dichloroquinolines. The hydrazinylquinolines were subsequently converted into aminoquinoline substituted pyrrolidin-2,5-diones in the presence

  通过2,4-二氯喹啉与水合肼的S N Ar反应合成了一类新的肼基喹啉区域异构体。反应在二氯喹啉的C 4位置而不是C 2位置处以具有高区域选择性的单取代产物终止。随后在伊顿试剂的存在下将肼基喹啉转化为氨基喹啉取代的吡咯烷-2，5-二酮。