2,5-diphenylpyrazolo[5,1-a]isoquinoline | 1174271-14-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,5-diphenylpyrazolo[5,1-a]isoquinoline
• 英文别名: 2,5-Diphenylpyrazolo[5,1-a]isoquinoline
• CAS: 1174271-14-7
• 化学式: C₂₃H₁₆N₂
• 分子量: 320.393
• InChiKey: AAVXWMLNOCVOPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  C₂₃H₁₆N₂ 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.33h， 以97%的产率得到2,5-diphenylpyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Cu-Catalyzed alkynylation–cyclization cascade for the construction of the pyrazolo[5,1-a]isoquinoline skeleton

  摘要：

  开发了铜催化的 3-(2-溴苯基)吡唑与末端炔烃的 Sonogashira 型偶联以及随后在同一罐中的亲电环化，以得到吡唑并[5,1-a]异喹啉。该转化无需使用钯或配体即可进行，而银添加剂是有益的。

  DOI：

  10.1039/c3ra40270c

文献信息

• AgOTf-catalyzed tandem reaction of N′-(2-alkynylbenzylidene)hydrazide with alkyne
  作者：Zhiyuan Chen、Xiaodi Yang、Jie Wu

  DOI：10.1039/b904498a

  日期：——

  AgOTf-catalyzed tandem reactions of N'-(2-alkynylbenzylidene)hydrazides with various alkynes under mild conditions are described, which generate fused 1,2-dihydroisoquinolines in good to excellent yields.

  描述了在温和的条件下，N'-（2-炔基亚苄基）酰肼与各种炔烃的AgOTf催化串联反应，该反应以良好或极好的收率产生了稠合的1,2-二氢异喹啉。
• Metal Cocatalyzed Tandem Alkynylative Cyclization Reaction of in Situ Formed<i>N</i>-Iminoisoquinolinium Ylides with Bromoalkynes via C–H Bond Activation
  作者：Ping Huang、Qin Yang、Zhiyuan Chen、Qiuping Ding、Jingshi Xu、Yiyuan Peng

  DOI：10.1021/jo3013429

  日期：2012.9.21

  Silver triflate and copper(I) iodide cocatalyzed direct alkynylation and cyclization reaction of in situ formed N-iminoisoquinolinium ylides with bromoalkynes is described. The reaction proceeds efficiently through a combination of C–H activation and subsequent tandem reaction in one pot, leading to diverse H-pyrazolo[5,1-a]isoquinolines in good yields under mild reaction conditions.

  描述了三氟甲磺酸银和碘化铜（I）共同催化原位形成的N-亚氨基异喹啉鎓碘化物与溴炔烃的直接炔基化和环化反应。在一个反应​​釜中，通过C–H活化和随后的串联反应的组合，该反应得以有效进行，从而在温和的反应条件下以高收率产生了多种H-吡唑并[5,1- a ]异喹啉。
• Ruthenium-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles <i>via</i> C–H/N–H bond functionalizations
  作者：Zhangpei Chen、Zhiqiang Ding、Tian Chen、Lingxin Meng、Gongshu Wang

  DOI：10.1039/d0ob01899f

  日期：——

  An efficient method for the construction of various pyrazolo[5,1-a]isoquinolines has been achieved via Ru(II)-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles. This oxidant-free transformation occurred through pyrazole-directed C–H activation, Ru-carbene insertion, and acid-promoted carbonyl condensation processes, enabling dual C–C and C–N bond formation. A broad

  一种有效的构建各种吡唑并[5,1- a ]异喹啉的方法是通过Ru( II )催化的α-羰基氧化鎓叶立德与芳基取代的吡唑环化。这种无氧化剂转化通过吡唑导向的 C-H 活化、Ru-卡宾插入和酸促进的羰基缩合过程发生，从而形成双 C-C 和 C-N 键。两个耦合组件的广泛底物范围以高产率有效地工作。
• Palladium-catalyzed oxidation of amine in air: an efficient approach to H-pyrazolo[5,1-a]-isoquinolines
  作者：Jie Sheng、Ying Guo、Jie Wu

  DOI：10.1016/j.tet.2013.05.066

  日期：2013.8

  An efficient approach to H-pyrazolo[5,1-a]isoquinolines through a reaction of N'-(2-alkynylbenzylidene) hydrazide with amine in the presence of a cooperative catalysis under mild conditions is reported. The palladium-catalyzed oxidation of amine in air leading to the formation of enamine is the key step during the transformation. (C) 2013 Elsevier Ltd. All rights reserved.
• Route to Pyrazolo[5,1-<i>a</i>]isoquinolines via a Copper-Catalyzed Tandem Reaction of 2-Alkynylbromobenzene with Pyrazole
  作者：Xiaolin Pan、Yong Luo、Jie Wu

  DOI：10.1021/jo400523v

  日期：2013.6.7

  A copper-catalyzed tandem reaction of 2-alkynylbromobenzene and pyrazole is described that provides a facile route to pyrazolo[5,1-a]isoquinolines in good yields. During the reaction process, copper(1)-catalyzed hydroamination and C-H activation are involved.