1-(phenylethynyl)-1H-indazole | 1206196-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-(phenylethynyl)-1H-indazole
• 英文别名: 1-(2-Phenylethynyl)indazole
• CAS: 1206196-91-9
• 化学式: C₁₅H₁₀N₂
• 分子量: 218.258
• InChiKey: MMXPTULOWYXZPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(phenylethynyl)-1H-indazole 、 2-(2-fluoropyridin-1-ium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl]ethan-1-ide 以 乙腈 为溶剂， 反应 3.0h， 以100%的产率得到
  参考文献：
  名称：

  杂原子功能化的环丁烯三氟酮和环丁烯酮的区域选择性合成

  摘要：

  从杂原子取代的炔烃和吡啶鎓盐（潜在的Tf 2 C = CH 2来源）开始，开发了可控制的无金属合成各种杂原子的环丁烯-triflones [双（三氟甲基磺酰基）环丁烯]和环丁烯酮。。这种强大的方法涉及环化反应，可以选择性地制备氧，氮，溴，氯，碘，硫，硒，碲，磷和硅官能化的环丁烯衍生物。

  DOI：

  10.1002/adsc.201700492
• 作为产物：
  描述：

  吲唑 、 苯基溴乙炔 在 copper(l) iodide 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以72%的产率得到1-(phenylethynyl)-1H-indazole
  参考文献：
  名称：

  Cu-Catalyzed N-Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and Pyrazoles Using PEG as Solvent Medium

  摘要：

  A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive. We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.

  DOI：

  10.1021/jo902466f

文献信息

• Copper-Mediated Selective Cross-Coupling of 1,1-Dibromo-1-alkenes and Heteronucleophiles: Development of General Routes to Heterosubstituted Alkynes and Alkenes
  作者：Kévin Jouvin、Alexis Coste、Alexandre Bayle、Frédéric Legrand、Ganesan Karthikeyan、Krishnaji Tadiparthi、Gwilherm Evano

  DOI：10.1021/om3005614

  日期：2012.11.26

  site-selective, double, or alkynylative cross-coupling, therefore providing divergent and straightforward entries to numerous building blocks such as bromoenamides, ynamides, ketene N,N-acetals, bromoenol ethers, ynol ethers, ketene O,O-acetals, or vinylphosphonates and further expanding the copper catalysis toolbox with useful and versatile processes.

  据报道，有效的和通用的程序是将1，1-二溴代烯烃与N-，O-和P-亲核试剂进行交叉偶联。反应条件的微调允许位点选择性，双重或炔基交叉偶联，因此为许多结构单元（如溴酰胺，乙酰胺，乙烯酮N，N-乙缩醛，溴烯醇醚，炔醇醚）提供了分散而直接的入口，乙烯酮O，O-乙缩醛或乙烯基膦酸酯，并通过有用的通用方法进一步扩展了铜催化工具箱。
• Regioselective Synthesis of Heteroatom-Functionalized Cyclobutene-triflones and Cyclobutenones
  作者：Benito Alcaide、Pedro Almendros、Carlos Lázaro-Milla

  DOI：10.1002/adsc.201700492

  日期：2017.8.7

  synthesis of a vast variety of heteroatom‐containing cyclobutene‐triflones [bis(trifluoromethylsulfonyl)cyclobutenes] and cyclobutenones has been developed starting from heteroatom‐substituted alkynes and a pyridinium salt (a latent Tf2C=CH2 source). This powerful methodology, involving cyclization reactions, allows for the selective preparation of oxygen‐, nitrogen‐, bromine‐, chlorine‐, iodine‐, sulfur‐

  从杂原子取代的炔烃和吡啶鎓盐（潜在的Tf 2 C = CH 2来源）开始，开发了可控制的无金属合成各种杂原子的环丁烯-triflones [双（三氟甲基磺酰基）环丁烯]和环丁烯酮。。这种强大的方法涉及环化反应，可以选择性地制备氧，氮，溴，氯，碘，硫，硒，碲，磷和硅官能化的环丁烯衍生物。
• Cu-Catalyzed N<i>-</i>Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and Pyrazoles Using PEG as Solvent Medium
  作者：Glenn A. Burley、David L. Davies、Gerry A. Griffith、Michael Lee、Kuldip Singh

  DOI：10.1021/jo902466f

  日期：2010.2.5

  A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive. We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.