(1-hydroxy-propyl)-phosphonic acid dipropyl ester | 149053-00-9

• 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: (1-hydroxy-propyl)-phosphonic acid dipropyl ester
• 英文别名: (1-Hydroxy-propyl)-phosphonsaeure-dipropylester；1-Dipropoxyphosphorylpropan-1-ol
• CAS: 149053-00-9
• 化学式: C₉H₂₁O₄P
• 分子量: 224.237
• InChiKey: IQHZPKARNWGJMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  磷酸三丙酯 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 3.0h， 以66%的产率得到(1-hydroxy-propyl)-phosphonic acid dipropyl ester
  参考文献：
  名称：

  The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications V. On the reaction ofs-butyllithium/TMEDA with symmetrical trialkyl phosphates

  摘要：

  1-(Tributylstannyl)hexanol ((+/-)-8) is phosphorylated to give phosphate (+/-)-9 which is then transmetallated. The organolithium intermediate (+/-)-10 isomerizes to alpha-hydroxyphosphonate (+/-)-12. Similar intermediates are also formed upon direct deprotonation of triethyl, tri-n-propyl, and tri-n-butyl phosphate, which subsequently rearrange to alpha-hydroxyphosphonates (+/-)-14a-c.

  DOI：

  10.1007/bf00807567

文献信息

• Abramow; Ilina, Zhurnal Obshchei Khimii, 1954, vol. 24, p. 124;engl.Ausg.S.121
  作者：Abramow、Ilina

  DOI：——

  日期：——
• The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications V. On the reaction ofs-butyllithium/TMEDA with symmetrical trialkyl phosphates
  作者：F. Hammerschmidt、S. Schmidt

  DOI：10.1007/bf00807567

  日期：1997.11

  1-(Tributylstannyl)hexanol ((+/-)-8) is phosphorylated to give phosphate (+/-)-9 which is then transmetallated. The organolithium intermediate (+/-)-10 isomerizes to alpha-hydroxyphosphonate (+/-)-12. Similar intermediates are also formed upon direct deprotonation of triethyl, tri-n-propyl, and tri-n-butyl phosphate, which subsequently rearrange to alpha-hydroxyphosphonates (+/-)-14a-c.