3-chloro-1-hydroxypropane-2-yl | 53693-04-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 3-chloro-1-hydroxypropane-2-yl
• 英文别名: O-(1-Chlormethyl-2-hydroxyethyl)-phosphonat；phosphonic acid mono-(β-chloro-β'-hydroxy-isopropyl ester)；Phosphonsaeure-mono-(β-chlor-β'-hydroxy-isopropylester)
• CAS: 53693-04-2
• 化学式: C₃H₈ClO₄P
• 分子量: 174.521
• InChiKey: ZVUSMCQPFWAFCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 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：

  环氧氯丙烷 在 亚磷酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以8%的产率得到2-oxo-4-chloromethyl-1,3,2-dioxaphospholane
  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