5-chloroisoquinoline-1-carbonitrile | 1231761-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-chloroisoquinoline-1-carbonitrile
• CAS: 1231761-25-3
• 化学式: C₁₀H₅ClN₂
• 分子量: 188.616
• InChiKey: CEZFJHXSHFEQRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  5-chloroisoquinoline-1-carbonitrile 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,2'S)-N,N'-(4,4'-((E)-ethene-1,2-diyl)bis(4,1-phenylene))bis(1-(5-chloroisoquinoline-1-carbonyl)pyrrolidine-2-carboxamide)
  参考文献：
  名称：

  HCV NS5A Replication Complex Inhibitors. Part 4.1 Optimization for Genotype 1a Replicon Inhibitory Activity

  摘要：

  A series of symmetrical E-stilbene prolinamides that originated from the library-synthesized lead 3 was studied with respect to HCV genotype 1a (G-1a) and genotype 1b (G-1b) replicon inhibition and selectivity against BVDV and cytotoxicity. SAR emerging from an examination of the prolinamide cap region revealed 11 to be a selective HCV NS5A inhibitor exhibiting submicromolar potency against both G-1a and G-1b replicons. Additional structural refinements resulted in the identification of 30 as a potent, dual G-1a/1b HCV NS5A inhibitor.

  DOI：

  10.1021/jm301796k
• 作为产物：
  描述：

  potassium cyanide 、 1,5-二氯异喹啉 在 四甲基乙二胺 、 1,5-双(二苯基膦)戊烷 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 以52%的产率得到5-chloroisoquinoline-1-carbonitrile
  参考文献：
  名称：

  HCV NS5A Replication Complex Inhibitors. Part 4.1 Optimization for Genotype 1a Replicon Inhibitory Activity

  摘要：

  A series of symmetrical E-stilbene prolinamides that originated from the library-synthesized lead 3 was studied with respect to HCV genotype 1a (G-1a) and genotype 1b (G-1b) replicon inhibition and selectivity against BVDV and cytotoxicity. SAR emerging from an examination of the prolinamide cap region revealed 11 to be a selective HCV NS5A inhibitor exhibiting submicromolar potency against both G-1a and G-1b replicons. Additional structural refinements resulted in the identification of 30 as a potent, dual G-1a/1b HCV NS5A inhibitor.

  DOI：

  10.1021/jm301796k

文献信息

• Site‐Selective <i>N</i> ‐1 and C‐3 Heteroarylation of Indole with Heteroarylnitriles by Organocatalysis under Visible Light
  作者：Chao Zhou、Qi‐Chao Gan、Tai‐Ping Zhou、Tao Lei、Chen Ye、Xiao‐Jun He、Bin Chen、Heng Lu、Qian Wan、Rong‐Zhen Liao、Chen‐Ho Tung、Li‐Zhu Wu

  DOI：10.1002/anie.202116421

  日期：2022.3

  C-3 heteroarylation of indoles via radical–radical cross-coupling by visible light irradiation have been developed with the aid of organocatalysis. Mechanism studies revealed that the reaction pathway switches from energy-transfer to proton-coupled electron-transfer by consecutive hydrogen-bonding association between the organic base and its conjugate acid, with the radical species of the indole and

  借助有机催化，通过可见光照射通过自由基-自由基交叉偶联对吲哚进行N -1 和 C-3 杂芳基化的第一个区域选择性平行方法已被开发出来。机理研究表明，通过有机碱与其共轭酸、吲哚和杂芳基腈的自由基物种之间的连续氢键结合，反应途径从能量转移转变为质子耦合电子转移。