2-(2-bromophenyl)-1H-perimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类 - 二氮杂萘
• 英文名称: 2-(2-bromophenyl)-1H-perimidine
• 化学式: C₁₇H₁₁BrN₂
• 分子量: 323.192
• InChiKey: OKYPNTZGMPHJCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  氰乙酸正丁酯 、 2-(2-bromophenyl)-1H-perimidine 在 copper(l) iodide 、 碳酸氢钠 、 L-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到n-butyl 13-aminoisoquinolino[2,1-a]perimidine-12-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of 13-Aminoisoquinolino[2,1-a ]perimidine-12-carboxylates via α-Arylation with a High Chemoselectivity

  摘要：

  The α‐arylation between cyanoacetate and 2‐(2‐bromophenyl)‐1H‐perimidine took place first catalyzed by CuI/L‐proline in the presence of NaHCO3, and then the amino on perimidine chemoselectively attacked the cyano group to undergo a nucleophilic addition, giving a series of 13‐aminoisoquinolino[2,1‐a]perimidine‐12‐carboxylate derivatives in good yields.

  DOI：

  10.1002/jhet.3445

文献信息

• Synthesis of pyrimidine-fused skeletons through copper-catalyzed consecutive Sonogashira coupling and aminocyclization
  作者：Heng He、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1039/d3ob01248d

  日期：——

  A copper-catalyzed sequence involving a Sonogashira coupling reaction and 5-exo-dig aminocyclization between a terminal alkyne and a 2-(2-bromophenyl)pyrimidine analog based on six-membered rings is presented. This protocol provides a controlled and modular approach to access a variety of synthetically useful pyrimidine-fused skeletons with high efficiency, broad substrate scope, and excellent functional

  提出了铜催化序列，涉及 Sonogashira 偶联反应和末端炔烃与基于六元环的 2-(2-溴苯基)嘧啶类似物之间的5- exo-dig氨基环化。该协议提供了一种受控和模块化的方法来访问各种合成有用的嘧啶融合骨架，具有高效率、广泛的底物范围和出色的官能团兼容性。在酸性条件下，产物的( Z )-构型自发转化为( E )-9-亚苄基-1,9-二氢-11H-吡唑并[4',3':4,5]嘧啶基[2,1- a ]异吲哚-11-酮。
• Novel perimidines, their preparation, formulations and use as immunosuppressives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0002906A2

  公开（公告）日：1979-07-11

  Novel 2-aryl-1H-perimidine compounds, which are useful as immunosuppressive agents, are described herein. The compounds are prepared by the condensation of 1,8-diaminonaphthalene with an appropriate acyl compound.

  本文描述了可用作免疫抑制剂的新型 2-芳基-1H-哌啶化合物。这些化合物是通过 1,8-二氨基萘与适当的酰基化合物缩合制备的。
• Copper-Catalyzed Synthesis of 13-Aminoisoquinolino[2,1-<i>a</i> ]perimidine-12-carboxylates <i>via</i> α-Arylation with a High Chemoselectivity
  作者：Meng-Qiao Huang、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1002/jhet.3445

  日期：2019.2

  The α‐arylation between cyanoacetate and 2‐(2‐bromophenyl)‐1H‐perimidine took place first catalyzed by CuI/L‐proline in the presence of NaHCO3, and then the amino on perimidine chemoselectively attacked the cyano group to undergo a nucleophilic addition, giving a series of 13‐aminoisoquinolino[2,1‐a]perimidine‐12‐carboxylate derivatives in good yields.