丙基膦酸单甲酯 | 53621-95-7

• 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
• 中文名称: 丙基膦酸单甲酯
• 英文名称: Monomethyl propylphosphonic acid
• 英文别名: methyl hydrogen propylphosphonate；Propylphosphonic acid methyl ester；methoxy(propyl)phosphinic acid
• CAS: 53621-95-7
• 化学式: C₄H₁₁O₃P
• 分子量: 138.103
• InChiKey: RLDXWNAZJDJGCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 丙基膦酸单甲酯 在 氯化亚砜 作用下， 反应 2.0h， 生成 P-丙基-膦酸二甲酯
  参考文献：
  名称：

  利用 P-烷基 2,3-氧杂磷杂双环 [2.2.2] 辛烯 3-氧化物前体对亲核试剂进行片段化相关的膦酰化

  摘要：

  新的 P-烷基 2,3-氧杂磷杂双环-[2.2.2] 辛烯 3-氧化物是通过相应的 7-磷酰冰片烯 7-氧化物的 Bayer-Villiger 氧化合成的，并用作反应性烷基偏膦酸酯的前体，可用于醇的膦酰化. 这是第一个通过 O 插入形成的两种区域异构体的反应性不同的情况，并且在微波辅助条件下实现了导致膦酸酯的断裂相关的膦酰化。

  DOI：

  10.1002/hc.21304
• 作为产物：
  描述：

  甲醇 、 丙基膦酸 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以72%的产率得到丙基膦酸单甲酯
  参考文献：
  名称：

  The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines

  摘要：

  A variety of methods have been explored for the convergent synthesis of phosphonamidates and phosphonates via phosphonochloridates. In the absence of complex functionality, phosphorus pentachloride is an effective reagent for the conversion of diethyl and diisopropyl phosphonates to phosphonochloridates. Subsequent reaction with amines and alcohols provides good yields of the phosphonamidates and mixed phosphonates, respectively. However, in the presence of more complex functionality, a milder method utilizing oxalyl chloride to generate the phosphonochloridate from a monomethyl phosphonic acid is required. Aminolysis of the dimethyl phosphonates generates the requisite monomethyl phosphonic acids which are cleanly converted to phosphonochloridates and reacted with amines and primary alcohols.

  DOI：

  10.1021/jo00104a016

文献信息

• SYNTHESIS OF ALKYL HYDROGEN ALKYLPHOSPHONATES
  作者：André Pienaar、Cornelis M. Erasmus、Mauritz Wentzel、Eugene H. Cowley

  DOI：10.1080/10426509908037007

  日期：1999.5.1

  The synthesis of alkyl hydrogen alkylphosphonates 1 was studied. Different synthetic routes were investigated and it was found that alkylphosphonic anhydrides can serve as ideal precursors for the synthesis of those half-acids, It was also shown that isopropyl phosphonic dichloride reacts in a unique fashion to produce alkyl hydrogen isopropylphosphonates in moderate yields.
• Fragmentation-Related Phosphonylation of Nucleophiles Utilizing P-Alkyl 2,3-oxaphosphabicyclo[2.2.2]octene 3-oxide Precursors
  作者：Tamara Kovács、Laura Szandra Fülöp、György Keglevich

  DOI：10.1002/hc.21304

  日期：2016.3

  New P-alkyl 2,3-oxaphosphabicyclo-[2.2.2]octene 3-oxides were synthesized by the Bayer–Villiger oxidation of the corresponding 7-phosphanorbornene 7-oxides and were used as precursors for reactive alkylmetaphosphonates useful in the phosphonylation of alcohols. This is the first case that the reactivity of the two regioisomers formed by O-insertion was differentiated and that the fragmentation-related

  新的 P-烷基 2,3-氧杂磷杂双环-[2.2.2] 辛烯 3-氧化物是通过相应的 7-磷酰冰片烯 7-氧化物的 Bayer-Villiger 氧化合成的，并用作反应性烷基偏膦酸酯的前体，可用于醇的膦酰化. 这是第一个通过 O 插入形成的两种区域异构体的反应性不同的情况，并且在微波辅助条件下实现了导致膦酸酯的断裂相关的膦酰化。
• The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines
  作者：William P. Malachowski、James K. Coward

  DOI：10.1021/jo00104a016

  日期：1994.12

  A variety of methods have been explored for the convergent synthesis of phosphonamidates and phosphonates via phosphonochloridates. In the absence of complex functionality, phosphorus pentachloride is an effective reagent for the conversion of diethyl and diisopropyl phosphonates to phosphonochloridates. Subsequent reaction with amines and alcohols provides good yields of the phosphonamidates and mixed phosphonates, respectively. However, in the presence of more complex functionality, a milder method utilizing oxalyl chloride to generate the phosphonochloridate from a monomethyl phosphonic acid is required. Aminolysis of the dimethyl phosphonates generates the requisite monomethyl phosphonic acids which are cleanly converted to phosphonochloridates and reacted with amines and primary alcohols.