β-hydroxyethyl H-phosphonate | 24660-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-hydroxyethyl H-phosphonate
• 英文别名: 2-hydroxyethyl H-phosphonate；2-hydroxyethyl phosphonate
• CAS: 24660-28-4
• 化学式: C₂H₇O₄P
• 分子量: 126.049
• InChiKey: ACXJKDUFAXMPOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  7.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  环氧乙烷 在 亚磷酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以10%的产率得到β-hydroxyethyl H-phosphonate
  参考文献：
  名称：

  H-TETRAOXASPIROPHOSPHORANES AS POSSIBLE INTERMEDIATES IN THE PHOSPHONYLATION BY PHOSPHOROUS ACID/OXIRANES

  摘要：

  The detailed P-31-NMR study of the mechanism of the ribozymomimetic phosphorylation with phosphorous acid / oxirane revealed consecutive formation of beta -hydroxy H-phosphonate monoester, di-(beta -hydroxyalkyl) H-phosphonate, alkylene H-phosphonate, beta -hydroxy alkyl alkylene phosphite and the corresponding stereoelectronically stabilized penracoordinated H-tetraoxaspirophosphorane. The equilibrium between the triphosphite and the spirophosphorane shifts towards the beta -hydroxyalkyl alkylene phosphite at high temperatures. In the presence of alcohol and controlled amounts of water transesterification of the beta -hydroxyalkyl alkylene phosphite to the corresponding alkyl alkylene phosphite, and hydrolysis to beta -hydroxyalkyl alkyl H-phosphonate proceed at the elevated temperature. beta -Hydroxyalkyl alkyl H-phosphonates are model compounds of the phosphodiester bond and undergo hydrolysis with a diol leaving in the presence of one equivalent of water.

  DOI：

  10.1080/10426500008076540

文献信息

• Microwave-assisted alcoholysis of dialkyl <i>H</i>-phosphonates by diols and amino alcohols
  作者：Ádám Tajti、György Keglevich、Erika Bálint

  DOI：10.1080/10426507.2017.1284841

  日期：2017.6.3

  GRAPHICAL ABSTRACT ABSTRACT The microwave-assisted alcoholysis of dialkyl H-phosphonates with diols and amino alcohols aiming at P-functionalized monomers was studied. Depending on the conditions (molar ratio, temperature, time), the reaction could be fine-tuned to afford the target mono and bis hydroxyalkyl or aminoalkyl H-phopshonate derivatives. The formation of three types of by-products was also

  图形摘要 摘要 针对 P 官能化单体，研究了 H-膦酸二烷基酯与二醇和氨基醇的微波辅助醇解。根据条件（摩尔比、温度、时间），可以对反应进行微调以提供目标单和双羟烷基或氨基烷基 H-膦酸酯衍生物。还研究了三种副产物的形成。热成就显示酯交换的效率较低。
• H-TETRAOXASPIROPHOSPHORANES AS POSSIBLE INTERMEDIATES IN THE PHOSPHONYLATION BY PHOSPHOROUS ACID/OXIRANES
  作者：Svetomir B. Tzokov、Nikolay G. Vassilev、Rositza T. Momtcheva、Jose Kaneti、Dimiter D. Petkova

  DOI：10.1080/10426500008076540

  日期：2000.1.1

  The detailed P-31-NMR study of the mechanism of the ribozymomimetic phosphorylation with phosphorous acid / oxirane revealed consecutive formation of beta -hydroxy H-phosphonate monoester, di-(beta -hydroxyalkyl) H-phosphonate, alkylene H-phosphonate, beta -hydroxy alkyl alkylene phosphite and the corresponding stereoelectronically stabilized penracoordinated H-tetraoxaspirophosphorane. The equilibrium between the triphosphite and the spirophosphorane shifts towards the beta -hydroxyalkyl alkylene phosphite at high temperatures. In the presence of alcohol and controlled amounts of water transesterification of the beta -hydroxyalkyl alkylene phosphite to the corresponding alkyl alkylene phosphite, and hydrolysis to beta -hydroxyalkyl alkyl H-phosphonate proceed at the elevated temperature. beta -Hydroxyalkyl alkyl H-phosphonates are model compounds of the phosphodiester bond and undergo hydrolysis with a diol leaving in the presence of one equivalent of water.