hexaethyl pent-4-yne-1,2,2-tris(phosphonate) | 860646-48-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: hexaethyl pent-4-yne-1,2,2-tris(phosphonate)
• 英文别名: 4,4,5-Tris[diethoxy(oxido)phosphaniumyl]pent-1-yne；4,4,5-tris[diethoxy(oxido)phosphaniumyl]pent-1-yne
• CAS: 860646-48-6
• 化学式: C₁₇H₃₅O₉P₃
• 分子量: 476.381
• InChiKey: DXBUTTQBUDETAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  hexaethyl pent-4-yne-1,2,2-tris(phosphonate) 、 5-叠氮戊腈 在 copper(I) sulfate 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 72.0h， 以70%的产率得到hexaethyl 3-[1-(4-cyanobutyl)-1H-1,2,3-triazol-4-yl]propyl-1,2,2-triphosphonate
  参考文献：
  名称：

  Synthesis of triazolyl-alkylphosphonate starting from ω-azidoalkylphosphonates or ω-alkynylphosphonates

  摘要：

  1,2,3-Triazolyl-alkylphosphonates are synthesised according to a Huisgen 1,3-dipolar cycloaddition catalysed by copper salts. The cycloaddition of either an alkynylphosphonate with an azidoalkane or an azido-phosphonate with an alkyne is achieved in high yield and regiospecifically. As an illustration of the functionalisation of aromatic ligands by using the catalytic version of the Huisgen reaction, the coupling of 3-ethynyl-1,10-phenanthroline with azidoalkylphosphonate is reported. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.024
• 作为产物：
  描述：

  1,1-双(二乙氧基磷酰基)乙烯 在 sodium ethanolate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.33h， 生成 hexaethyl pent-4-yne-1,2,2-tris(phosphonate)
  参考文献：
  名称：

  Michael addition of phosphorus derivatives on tetraethyl ethylidenediphosphonate

  摘要：

  Nucleophilic phosphorus add to tetraethyl ethylidene diphosphonate in protic solvent to yield the product of the Michael reaction. This reaction appeared to be reversible at a temperature upper than 160 degrees C. To avoid this reverse reaction, alkylation in g. position of the two phosphonate functions by activated elecrophile is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.045

文献信息

• ω-Alkyne-Mono- and Diphosphonates – Synthesis and Sonogashira Cross-Coupling Reaction with Aryl Halides
  作者：Lise Delain-Bioton、Didier Villemin、Paul-Alain Jaffrès

  DOI：10.1002/ejoc.200600556

  日期：2007.3

  A convergent approach to functionalise aromatic compounds with a linker terminated by a phosphonate group is reported. The starting point of this strategy is the synthesis of five new ω-alkyne-phosphonates. The linker between the phosphonate group and the alkyne part is either an alkyl or an ether chain. This strategy is based on the use of the phosphonate group as the anchoring point for the attachment

  报道了一种将芳族化合物功能化的收敛方法，该方法具有由膦酸酯基团封端的接头。该策略的起点是合成五种新的 ω-炔烃-膦酸酯。膦酸酯基团和炔部分之间的接头是烷基或醚链。该策略基于使用膦酸酯基团作为锚定点来连接
• Synthesis of triazolyl-alkylphosphonate starting from ω-azidoalkylphosphonates or ω-alkynylphosphonates
  作者：Lise Delain-Bioton、Didier Villemin、Jean-François Lohier、Jana Sopkova、Paul-Alain Jaffrès

  DOI：10.1016/j.tet.2007.07.024

  日期：2007.9

  1,2,3-Triazolyl-alkylphosphonates are synthesised according to a Huisgen 1,3-dipolar cycloaddition catalysed by copper salts. The cycloaddition of either an alkynylphosphonate with an azidoalkane or an azido-phosphonate with an alkyne is achieved in high yield and regiospecifically. As an illustration of the functionalisation of aromatic ligands by using the catalytic version of the Huisgen reaction, the coupling of 3-ethynyl-1,10-phenanthroline with azidoalkylphosphonate is reported. (c) 2007 Elsevier Ltd. All rights reserved.
• Michael addition of phosphorus derivatives on tetraethyl ethylidenediphosphonate
  作者：Lise Delain-Bioton、Adele Turner、Nicolas Lejeune、Didier Villemin、Gary B. Hix、Paul-Alain Jaffrès

  DOI：10.1016/j.tet.2005.04.045

  日期：2005.7

  Nucleophilic phosphorus add to tetraethyl ethylidene diphosphonate in protic solvent to yield the product of the Michael reaction. This reaction appeared to be reversible at a temperature upper than 160 degrees C. To avoid this reverse reaction, alkylation in g. position of the two phosphonate functions by activated elecrophile is reported. (c) 2005 Elsevier Ltd. All rights reserved.