tert-butyl phosphinate | 66447-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl phosphinate
• 英文别名: t-butylphosphinate；phosphinic acid tert-butyl ester；phosphonous acid mono-tert-butyl ester；(2-Methylpropan-2-yl)oxy-oxidophosphanium；(2-methylpropan-2-yl)oxy-oxidophosphanium
• CAS: 66447-17-4
• 化学式: C₄H₁₁O₂P
• 分子量: 122.104
• InChiKey: GCTIWQGPLSSWPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl phosphinate 、 (S)-N,N'-di(tert-butoxycarbonyl)-1,2-diamino-(4-iodophenyl)propane 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.67h， 以75%的产率得到tert-butyl (4-((2S)-di(tert-butoxycarbonylamino)propyl)phenyl)phosphinate
  参考文献：
  名称：

  Synthesis of a New Ligand for Metal Assembly to a Selective Receptor

  摘要：

  Diarylphosphinic acid 2, bearing two ethylenediamine groups, was designed with the aim of assembly to form a hydrophobic cavity upon binding to metals. The new ligand was prepared in optically active form from phenylalanine by an efficient sequence which required chromatography only for the P-C bond forming steps. Versatile intermediates in the synthesis are described. Complexes of this ligand with Zn2+ were shown to bind closely related aromatic guests bearing anionic tethered groups with 1000-fold discrimination.

  DOI：

  10.1021/jo9804590
• 作为产物：
  描述：

  叔丁醇 在 次磷酸 作用下， 以37%的产率得到tert-butyl phosphinate
  参考文献：
  名称：

  用于钯催化交叉偶联的次膦酸酯的改进制备

  摘要：

  次膦酸与原甲酸三甲酯之间的反应产生次膦酸甲酯，显示出明显的溶剂依赖性。确定条件以提高酯纯度。还可以干净地制备次膦酸叔丁酯，并报道了其与碘代芳基钯的钯催化反应。

  DOI：

  10.1016/0040-4039(95)02209-0

文献信息

• Improved preparation of phosphinate esters for palladium-catalyzed cross-coupling
  作者：Alan W Schwabacher、Andrei D Stefanescu

  DOI：10.1016/0040-4039(95)02209-0

  日期：1996.1

  The reaction between phosphinic acid and trimethyl orthoformate to yield methyl phosphinate shows a pronounced solvent dependence. Conditions are defined to improve ester purity. t-Butyl phosphinate is also prepared cleanly, and its palladium-catalyzed reaction with aryl iodide is reported.

  次膦酸与原甲酸三甲酯之间的反应产生次膦酸甲酯，显示出明显的溶剂依赖性。确定条件以提高酯纯度。还可以干净地制备次膦酸叔丁酯，并报道了其与碘代芳基钯的钯催化反应。
• Synthesis of a New Ligand for Metal Assembly to a Selective Receptor
  作者：Alan W. Schwabacher、Andrei D. Stefanescu、Atiq ur Rehman

  DOI：10.1021/jo9804590

  日期：1999.3.1

  Diarylphosphinic acid 2, bearing two ethylenediamine groups, was designed with the aim of assembly to form a hydrophobic cavity upon binding to metals. The new ligand was prepared in optically active form from phenylalanine by an efficient sequence which required chromatography only for the P-C bond forming steps. Versatile intermediates in the synthesis are described. Complexes of this ligand with Zn2+ were shown to bind closely related aromatic guests bearing anionic tethered groups with 1000-fold discrimination.