4-hydroxybut-1-yn-1-ylcoppe | 54502-25-9

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 4-hydroxybut-1-yn-1-ylcoppe
• 英文别名: (4-hydroxy-but-1-ynyl)-copper；Kupfer-β-aethanoylacetylid；Butin-(3)-ol-(1)-Kupfer
• CAS: 54502-25-9
• 化学式: C₄H₅CuO
• 分子量: 132.629
• InChiKey: FNZWKEWBLLWMRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-羟基-2-碘吡啶 、 4-hydroxybut-1-yn-1-ylcoppe 在 吡啶 作用下， 生成 2-furo[3,2-b]pyridin-2-yl-ethanol
  参考文献：
  名称：

  Mladenovic,S.A.; Castro,C.E., Journal of Heterocyclic Chemistry, 1968, vol. 5, p. 227 - 230

  摘要：

  DOI：
• 作为产物：
  描述：

  copper(l) iodide 、 3-丁炔-1-醇 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 以55%的产率得到4-hydroxybut-1-yn-1-ylcoppe
  参考文献：
  名称：

  Convenient and Practical Alkynylation of Heteronucleophiles with Copper Acetylides

  摘要：

  Copper acetylides, readily available reagents which are characterized by their lack of reactivity, can be simply activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles, including amides, oxazolidinones, imines, and dialkyl phosphites. This alkynylation, which provides one of the most practical entry to useful building blocks such as ynamides, ynimines, and alkynylphosphonates, proceeds under especially mild conditions and can be easily performed on a multigram scale.

  DOI：

  10.1055/s-0033-1341025

文献信息

• Unprecedented Synthesis of Alkynylphosphine-boranes through Room-Temperature Oxidative Alkynylation
  作者：Kévin Jouvin、Romain Veillard、Cédric Theunissen、Carole Alayrac、Annie-Claude Gaumont、Gwilherm Evano

  DOI：10.1021/ol402197d

  日期：2013.9.6

  An original and user-friendly synthesis of alkynylphosphine-boranes, useful building blocks in organic synthesis, based on an oxidative P-alkynylation reaction with readily available copper acetylides is reported. The ability of a secondary phosphine protected with a borane to undergo oxidative coupling without oxidation of the P-moiety is demonstrated for the first time. The reaction, which proceeds at room temperature, is applicable to the preparation of enantioenriched and structurally complex alkynylphosphine-boranes.
• Tandem Synthesis of 3-Chloro-4-iodoisoxazoles from 1-Copper(I) Alkynes, Dichloroformaldoxime, and Molecular Iodine
  作者：Wenwen Chen、Jianlan Zhang、Bo Wang、Zhouxing Zhao、Xinyan Wang、Yuefei Hu

  DOI：10.1021/jo502634h

  日期：2015.2.20

  A tandem synthesis for structurally novel 3-chloro-4-iodoisoxazoles was developed by simply mixing 1-copper(I) alkynes, dichloroformaldoxime, and molecular iodine together. The combination of 1-copper(I) alkyne and molecular iodine was well used as a synthetic equivalent of 1-iodoalkyne without the need for tedious preparation, purification, and storage of 1-iodoalkyne.