(tert-butoxycarbonyl)ethynylcopper | 101067-48-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (tert-butoxycarbonyl)ethynylcopper
• CAS: 101067-48-5
• 化学式: C₇H₉CuO₂
• 分子量: 188.693
• InChiKey: XVPISIPGQQULFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  亚磷酸二异丙酯 、 (tert-butoxycarbonyl)ethynylcopper 在 N-甲基咪唑 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以48%的产率得到diisopropyl (tert-butoxycarbonylethynyl)phosphonate
  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
• 作为产物：
  描述：

  copper(l) iodide 、 叔丁基丙炔酸酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 以76%的产率得到(tert-butoxycarbonyl)ethynylcopper
  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

• 3-(4-iodomethyl-2-oxo-1-azetidinyl)propynoic acidt-butyl ester: a new β-lactam derivative, synthesis of an ynamide by reaction of 4-iodomethylazetidin-2-one with the t-butyl ester of propiolic acid in the presence of copper(i)
  作者：Aldo Balsamo、Bruno Macchia、Franco Macchia、Armando Rossello、Paolo Domiano

  DOI：10.1016/s0040-4039(00)89314-4

  日期：1985.1

  The reaction of 4-iodomethylazetidin-2-one (2) with the t-butyl ester of propiolic acid (4) in the presence both of equimolar amounts of copper(I) and oxygen results unexpectedly in the fomation of the β-lactam ynamide 5. Its structure was suggested by spectroscopic data and confirmed by single-crystal X-ray analysis.

  在等摩尔量的铜（I）和氧存在下，4-碘甲基氮杂环丁烷-2-酮（2）与丙酸叔丁酯（4）的反应出乎意料地导致了β-内酰胺基酰胺的形成5.其结构由光谱数据暗示并由单晶X射线分析证实。
• 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.
• BALSAMO, A.;MACCHIA, B.;MACCHIA, F.;ROSSELLO, A.;DOMIANO, P, TETRAHEDRON LETT., 1985, 26, N 34, 4141-4144
  作者：BALSAMO, A.、MACCHIA, B.、MACCHIA, F.、ROSSELLO, A.、DOMIANO, P

  DOI：——

  日期：——