6-fluoro-3-phenylisoquinoline | 1135308-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-fluoro-3-phenylisoquinoline
• CAS: 1135308-74-5
• 化学式: C₁₅H₁₀FN
• 分子量: 223.25
• InChiKey: MSGPKLNWYKHWTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [4-Fluoro-2-(2-phenylethynyl)phenyl]methylidenehydrazine 在 silver nitrate 作用下， 以 二甲基亚砜 为溶剂， 生成 6-fluoro-3-phenylisoquinoline
  参考文献：
  名称：

  用于合成 3-芳基异喹啉的硝酸银介导的环化/N-N 键裂解反应

  摘要：

  已经开发出一种前所未有的硝酸银介导的芳香腙向各种异喹啉的新转化。该方法涉及硝酸银促进芳香腙环化，然后N-N键断裂，在温和条件下具有广泛的底物范围。

  DOI：

  10.1055/s-0035-1562609

文献信息

• Cobalt‐Mediated Decarboxylative/Desilylative C−H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues
  作者：Kang Chen、Shan Lv、Ruizhi Lai、Zhongzhen Yang、Li Hai、Ruifang Nie、Yong Wu

  DOI：10.1002/ejoc.202101355

  日期：2022.4.27

  A Co(II)- mediated decarboxylative/desilylative C−H activation/annulation reaction for the synthesis of 3-arylisoquinoline derivatives has been developed with a good functional group tolerance and wide applications.

  Co(II) 介导的脱羧/脱甲硅烷基 C-H 活化/环化反应用于合成 3-芳基异喹啉衍生物，具有良好的官能团耐受性和广泛的应用。
• Efficient Synthesis of Isoquinolines by AgNO₃-Catalyzed Sequential Imination-Annulation of 2-Alkynyl Aldehydes with Ammonium Bicarbonate
  作者：Yunhui Zhao、Mingjian Luo、Yubo Li、Xiong Liu、Zilong Tang、Keqin Deng、Gang Zhao

  DOI：10.1002/cjoc.201600277

  日期：2016.9

  An operationally simple approach for the tandem synthesis of isoquinolines by the reaction of o‐alkynylaldehydes with ammonium bicarbonate via Ag‐catalyzed 6‐endo‐dig ring closure is described. The reaction conditions and the scope of the reaction are examined, and a variety of substituted isoquinolines are prepared in moderate to excellent yields.

  描述了一种操作简单的方法，用于通过Ag催化的6-endo-dig环闭合使邻炔基醛与碳酸氢铵反应来串联合成异喹啉。检查了反应条件和反应范围，并以中等至优异的产率制备了各种取代的异喹啉。
• One-pot synthesis of isoquinoline and related compounds via Cu-mediated tandem cross-coupling and cyclization
  作者：Shubhendu Dhara、Raju Singha、Yasin Nuree、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2013.11.088

  日期：2014.1

  One-pot synthetic strategy has been developed to access isoquinolines and its analogs via Cu-mediated tandem cross-coupling and cyclization in good yields under mild reaction conditions. A mixture of suitably substituted α-bromoaldehyde, terminal alkyne, and aq NH3 in CuI/1,10-phenanathroline catalytic system afforded the 3-substituted isoquinoline regio-selectively in good to excellent yields.

  已经开发出一锅合成策略，以在温和的反应条件下通过铜介导的串联交叉偶联和环化以高收率获得异喹啉及其类似物。在CuI / 1，10-菲咯啉催化体系中适当取代的α-溴醛，末端炔烃和NH 3水溶液的混合物以良好或优异的收率选择性地生成3-取代的异喹啉。
• An efficient approach to isoquinoline via AgNO3-promoted 6-endo-dig cyclization followed by oxidative elimination of o-alkynylarylaldimines and its application in fluoride recognition
  作者：Yongxing Tang、Yajun Yu、Xinyu Wei、Jin Yang、Yeting Zhu、Yun-Hui Zhao、Zilong Tang、Zhihua Zhou、Xiaofang Li、Xianyong Yu

  DOI：10.1016/j.tetlet.2019.151187

  日期：2019.10

  by oxidation/elimination of o-alkynylarylaldimines with 4-hydroxybenzylamine was developed for preparation of isoquinolines. The intermediates of this tandem reaction were monitored by mass spectroscopy (MS) to confirm the reaction pathway. This methodology was further applied to the design and synthesis of a novel ratiometric chemosensor for determination of fluoride.

  为了制备异喹啉，开发了一种新颖的6-内切-环化反应，然后用4-羟基苄胺氧化/消除了o-炔基芳基醛亚胺。通过质谱（MS）监测该串联反应的中间体，以确认反应途径。该方法被进一步应用于设计和合成新型的用于测定氟化物的比例化学传感器。
• Study on the iodine-catalyzed reaction of 3-aminopyrazine-2-carbohydrazide and 2-(arylethynyl)benzaldehydes
  作者：Wan-Chen Pan、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1016/j.tet.2018.02.007

  日期：2018.3

  At 60 °C in DMSO, the iodine-catalyzed reaction of 3-aminopyrazine-2-carbohydrazide and 2-(arylethynyl)benzaldehydes led hydrazones. Increasing the reaction temperature to 100 °C, the amino and amido still indicated inactive, only the imine took part in the addition of acetylene bond to give 2-arylisoquinolines in high yields with the cleavage of N-N bond unexpectedly under metal-free conditions.

  在60°C的DMSO中，碘催化的3-氨基吡嗪-2-碳酰肼与2-（芳基乙炔基）苯甲醛的反应导致led。将反应温度提高至100°C，氨基和酰胺基仍然不活泼，只有亚胺参与乙炔键的添加，以高收率得到2-芳基异喹啉，在无金属条件下NN键意外地断裂。