(3-methyl-3H-imidazol-4-ylethynyl)-phosphonic acid diethyl ester | 912486-04-5

• 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: (3-methyl-3H-imidazol-4-ylethynyl)-phosphonic acid diethyl ester
• 英文别名: 5-(2-Diethoxyphosphorylethynyl)-1-methylimidazole
• CAS: 912486-04-5
• 化学式: C₁₀H₁₅N₂O₃P
• 分子量: 242.214
• InChiKey: ZLKNQXLCUYQHAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-methyl-3H-imidazol-4-ylethynyl)-phosphonic acid diethyl ester 、 亚磷酸二乙酯 在 三丁基膦 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以97%的产率得到[1-(diethoxyphosphoryl)-2-(3-methyl-3H-imidazol-4-yl)-vinyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Phosphine-Catalyzed α-P-Addition on Activated Alkynes: A New Route to P−C−P Backbones

  摘要：

  n-Tributylphosphine was found to efficiently catalyze the alpha-P addition of H-phosphonates, H-phosphinates, and H-phosphine oxide pronucleophiles on alkynes bearing phosphane oxide activating moieties. The reaction leads to 2-aryl-1-vinyl-1,1-diphosphane dioxide derivatives in good yields affording a new route to P - C - P backbones. The products of this reaction are easily converted to biologically important 1,1-bisphosphonates analogues.

  DOI：

  10.1021/ol061589v
• 作为产物：
  描述：

  氯磷酸二乙酯 、 5-乙炔基-1-甲基-1H-咪唑 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以66%的产率得到(3-methyl-3H-imidazol-4-ylethynyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Phosphine-Catalyzed α-P-Addition on Activated Alkynes: A New Route to P−C−P Backbones

  摘要：

  n-Tributylphosphine was found to efficiently catalyze the alpha-P addition of H-phosphonates, H-phosphinates, and H-phosphine oxide pronucleophiles on alkynes bearing phosphane oxide activating moieties. The reaction leads to 2-aryl-1-vinyl-1,1-diphosphane dioxide derivatives in good yields affording a new route to P - C - P backbones. The products of this reaction are easily converted to biologically important 1,1-bisphosphonates analogues.

  DOI：

  10.1021/ol061589v

文献信息

• Straightforward Synthesis of 2‐Aryl‐1‐alkynylphosphonates and Arylpropiolates
  作者：Delphine Lecerclé、Céline Mothes、Frédéric Taran

  DOI：10.1080/00397910701226830

  日期：2007.4.1

  Abstract A protocol for the direct cross coupling of trialkylsilyl‐alkynes bearing electron‐withdrawing groups and aryl halides using a Pd/Ag catalytic system is described. The procedure allows the straightforward synthesis of a variety of alkynylphosphonates and aryl propiolates derivatives in good yields.

  摘要描述了使用 Pd/Ag 催化系统直接交叉偶联带有吸电子基团的三烷基甲硅烷基炔烃和芳基卤化物的方案。该程序允许以良好的产率直接合成各种炔基膦酸酯和芳基丙炔酸酯衍生物。