dimethyl 1-formamidovinylphosphonate | 97147-56-3

• 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: dimethyl 1-formamidovinylphosphonate
• 英文别名: Dimethyl 1-(formamido)ethenyl-phosphonate；N-(1-dimethoxyphosphorylethenyl)formamide
• CAS: 97147-56-3
• 化学式: C₅H₁₀NO₄P
• 分子量: 179.112
• InChiKey: AKXKSJFYIHUUSG-UHFFFAOYSA-N

物化性质

• 沸点：
  339.1±38.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 1-formamidovinylphosphonate 在 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 99.5h， 生成 dimethyl (1R*,2R*)-2-{4-[(E)-2-(diethoxyphosphoryl)vinyl]phenyl}-1-formamidocyclopropylphosphonate
  参考文献：
  名称：

  Exploiting Palladium-Catalyzed Cross-Coupling for the Synthesis of 2-Aryl-Substituted 1-Aminocyclopropylphosphonates

  摘要：

  A series of 2-aryl-substituted 1-aminocyclopropylphosphonates containing an additional remote phosphonate group have been synthesized starting from readily accessible dimethyl (1R*,2R*)-2-(4-bromophenyl)-1-formamidocyclopropylphosphonate using cross-coupling methodology. Different types of palladium-catalyzed reactions for carbon-carbon and carbon-phosphorus bond formation were realized. In each case the optimum conditions were found to obtain the desired products in high yield in both small- and large-scale experiments.

  DOI：

  10.1055/s-0034-1378673
• 作为产物：
  描述：

  聚合甲醛 、 N-formamide 在 sodium methylate 作用下， 生成 dimethyl 1-formamidovinylphosphonate
  参考文献：
  名称：

  Schoellkopf, Ulrich; Hoppe, Inga; Thiele, Angelika, Liebigs Annalen der Chemie, 1985, # 3, p. 555 - 559

  摘要：

  DOI：

文献信息

• Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates
  作者：Nataliya S. Goulioukina、Nikolay N. Makukhin、Egor D. Shinkarev、Yuri K. Grishin、Vitaly A. Roznyatovsky、Irina P. Beletskaya

  DOI：10.1039/c6ob01780k

  日期：——

  5-Aryl-substituted pyrazol-3-ylphosphonates have been conveniently synthesized by 1,3-dipolar cycloaddition of 1-formamidovinylphosphonates and aryldiazomethanes under K2CO3/MeOH conditions at room temperature. These pyrazoles are formed in one pot via spontaneous elimination of formamide. Basic conditions prevent competitive formation of cyclopropylphosphonates. 3-Aryl substituted pyrazol-5-carboxylates

  通过在室温下在K 2 CO 3 / MeOH条件下将1-甲酰胺基乙烯基膦酸酯和芳基重氮甲烷进行1，3-偶极环加成，可以方便地合成5-芳基取代的吡唑-3-基膦酸酯。这些吡唑是通过自发消除甲酰胺而在一锅中形成的。碱性条件阻止竞争性形成环丙基膦酸酯。3-芳基取代的吡唑-5-羧酸酯可以通过相同的方法由1-芳基乙烯基膦酸酯和重氮乙酸乙酯合成，尽管为了确保芳构化阶段成功且消除二乙氧基磷酰基部分是必需的，更强的碱NaH是必需的。
• SCHOELLKOPF, U.;HOPPE, I.;THIELE, A., LIEBIGS ANN. CHEM., 1985, N 3, 555-559
  作者：SCHOELLKOPF, U.、HOPPE, I.、THIELE, A.

  DOI：——

  日期：——
• Schoellkopf, Ulrich; Hoppe, Inga; Thiele, Angelika, Liebigs Annalen der Chemie, 1985, # 3, p. 555 - 559
  作者：Schoellkopf, Ulrich、Hoppe, Inga、Thiele, Angelika

  DOI：——

  日期：——
• Exploiting Palladium-Catalyzed Cross-Coupling for the Synthesis of 2-Aryl-Substituted 1-Aminocyclopropylphosphonates
  作者：Nataliya Goulioukina、Alla Bessmertnykh-Lemeune、Nikolay Makukhin、Stéphane Brandès、Roger Guilard、Irina Beletskaya

  DOI：10.1055/s-0034-1378673

  日期：——

  A series of 2-aryl-substituted 1-aminocyclopropylphosphonates containing an additional remote phosphonate group have been synthesized starting from readily accessible dimethyl (1R*,2R*)-2-(4-bromophenyl)-1-formamidocyclopropylphosphonate using cross-coupling methodology. Different types of palladium-catalyzed reactions for carbon-carbon and carbon-phosphorus bond formation were realized. In each case the optimum conditions were found to obtain the desired products in high yield in both small- and large-scale experiments.