7-nitro-3-phenylisoquinoline | 1541897-97-5

• 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: 7-nitro-3-phenylisoquinoline
• 英文别名: 7-Nitro-3-phenylisoquinoline
• CAS: 1541897-97-5
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: LEDDPAFGHSBISK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻溴苄胺 在 1,1'-bis(di-tertbutylphosphino)ferrocene 、 硫酸 、 palladium diacetate 、 三正丁基氟化锡 、 potassium nitrate 、 三乙胺 、 cesium fluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.5h， 生成 7-nitro-3-phenylisoquinoline
  参考文献：
  名称：

  钯催化的甲硅烷基醚的α-芳基化在异喹啉和菲啶的合成中

  摘要：

  通过开发两步，一锅法，构成了区域选择性的钯催化的甲硅烷基醚的Kuwajima-Urabeα-芳基化和酸介导的脱保护，环化和芳构化，已经获得了各种各样的异喹啉和菲啶。甲硅烷基醚的结构多样性导致了三类不同的异喹啉和菲啶，可以从中衍生出相关的天然产物。还证明了通过快速组装天然产物三鸟苷可实现该方法的合成效用。

  DOI：

  10.1021/acs.orglett.7b03776

文献信息

• Hydrophilic Pd-phosphines catalyzed one-pot synthesis of substituted isoquinolines, furopyridines and thienopyridines in aqueous medium
  作者：Veeranna Guguloth、Narasimha Swamy Thirukovela、Ramesh Balaboina、Suresh Paidakula、Ravinder Vadde

  DOI：10.1016/j.tetlet.2018.12.035

  日期：2019.1

  A first example of simple and efficient hydrophilic Pd-phosphine complexes catalyzed one-pot three-component reaction of ortho-bromo aldehydes, terminal alkynes and ammonium acetate proceeds through the tandem coupling-imination-annulation path for the synthesis of substituted isoquinolines, furopyridines and thienopyridines in good to excellent yields in green aqueous medium at mild temperature was

  简单有效的亲水性Pd-膦配合物催化邻溴代乙醛，末端炔烃和乙酸铵的单锅三组分反应的第一个例子是通过串联偶联-胺化-环化路径进行的，用于合成取代的异喹啉，呋喃吡啶和描述了噻吩并吡啶在温和的温度下在绿色水性介质中具有良好至极好的收率。
• Synthesis of substituted isoquinolines via iminoalkyne cyclization using Ag(<scp>i</scp>) exchanged K10-montmorillonite clay as a reusable catalyst
  作者：Mariappan Jeganathan、Kasi Pitchumani

  DOI：10.1039/c4ra05026f

  日期：——

  Monosubstituted isoquinolines are synthesized in good to excellent yields by the Ag(I)-exchanged K10-montmorillonite clay catalyzed ring closure of iminoalkynes. This silver catalyzed ring closure is highly effective in cyclizing aryl- and alkyl-substituted iminoalkynes at 100 °C and accommodates a variety of iminoalkynes, thus affording a convenient route to the synthesis of isoquinolines. The other salient features of this procedure are its reusability, environmentally benign nature, high yield, operational simplicity with fewer steps, easy separation, and minimization of metallic wastes. The reaction proceeds smoothly in moderate yields and tolerates various functional groups. The solid catalyst can be readily recovered and reused. Notably, no additional base or other co-catalysts are needed. A plausible mechanism is proposed in which isoquinolines are formed via simultaneous bifunctional acid-base catalysis by Ag(I) clay.

  单取代异喹啉通过银(I)交换的K10膨润土催化的亚氨炔环化反应以良好到优异的产率合成。该银催化的环化反应在100°C下对芳基和烷基取代的亚氨炔有很高的高效性，并适应各种亚氨炔，从而提供了一条便捷的合成异喹啉的路线。该程序的其他显著特点包括可重复使用、环保、高产率、操作简单且步骤较少，易于分离，并减少金属废物。反应顺利进行，产率中等，并且耐受多种官能团。固体催化剂可以方便地回收和重复使用。值得注意的是，无需额外的碱或其他助催化剂。提出了一种合理的机制，通过银(I)粘土的双功能酸-碱催化同时生成异喹啉。
• 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。
• 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。
• Palladium-Catalyzed α-Arylation of Silylenol Ethers in the Synthesis of Isoquinolines and Phenanthridines
  作者：Gaurav Saini、Pravin Kumar、Gangam Srikanth Kumar、Arun Raj Kizhakkayil Mangadan、Manmohan Kapur

  DOI：10.1021/acs.orglett.7b03776

  日期：2018.1.19

  A diverse array of isoquinolines and phenanthridines have been accessed by developing a two-step, one-pot method constituting regioselective palladium-catalyzed Kuwajima–Urabe α-arylation of silylenol ethers and acid-mediated deprotection, annulation, and aromatization. Structural diversity in the silylenol ethers leads to three different classes of isoquinolines and phenanthridines from which related

  通过开发两步，一锅法，构成了区域选择性的钯催化的甲硅烷基醚的Kuwajima-Urabeα-芳基化和酸介导的脱保护，环化和芳构化，已经获得了各种各样的异喹啉和菲啶。甲硅烷基醚的结构多样性导致了三类不同的异喹啉和菲啶，可以从中衍生出相关的天然产物。还证明了通过快速组装天然产物三鸟苷可实现该方法的合成效用。