isopropyl hydrogen propylphosphonate

• 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: isopropyl hydrogen propylphosphonate
• 英文别名: Propan-2-yloxy(propyl)phosphinic acid
• 化学式: C₆H₁₅O₃P
• 分子量: 166.157
• InChiKey: DBNAWUMMZIKCGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 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：

  丙醇 、 isopropyl hydrogen propylphosphonate 在 polymer supported sulfonated magnetic resin 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以85%的产率得到O-isopropyl O'-propyl propylphosphonate
  参考文献：
  名称：

  聚合物负载的磺化磁性树脂：O-烷基烷基膦酸和羧酸酯化的有效试剂

  摘要：

  已经开发了一种温和而有效的合成方法，该方法使用聚合物负载的磺化磁性树脂对O-烷基烷基膦酸和羧酸进行酯化。使用外部磁体回收聚合物负载的树脂，并重复使用几次。

  DOI：

  10.1016/j.tetlet.2014.10.086
• 作为产物：
  描述：

  异丙醇 、 1-propanephosphonic acid cyclic anhydride 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以80.5%的产率得到isopropyl hydrogen propylphosphonate
  参考文献：
  名称：

  SYNTHESIS OF ALKYL HYDROGEN ALKYLPHOSPHONATES

  摘要：

  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.

  DOI：

  10.1080/10426509908037007

文献信息

• Microwave-Assisted Ionic Liquid-Catalyzed Selective Monoesterification of Alkylphosphonic Acids—An Experimental and a Theoretical Study
  作者：Nikoletta Harsági、Réka Henyecz、Péter Ábrányi-Balogh、László Drahos、György Keglevich

  DOI：10.3390/molecules26175303

  日期：——

  It is well-known that the P-acids including phosphonic acids resist undergoing direct esterification. However, it was found that a series of alkylphoshonic acids could be involved in monoesterification with C2–C4 alcohols under microwave (MW) irradiation in the presence of [bmim][BF4] as an additive. The selectivity amounted to 80–98%, while the isolated yields fell in the range of 61–79%. The method developed is a green method for P-acid esterification. DFT calculations at the M062X/6–311+G (d,p) level of theory (performed considering the solvent effect of the corresponding alcohol) explored the three-step mechanism, and justified a higher enthalpy of activation (160.6–194.1 kJ·mol−1) that may be overcome only by MW irradiation. The major role of the [bmim][BF4] additive is to increase the absorption of MW energy. The specific chemical role of the [BF4] anion of the ionic liquid in an alternative mechanism was also raised by the computations.

  众所周知，包括膦酸在内的P-酸不易直接酯化。然而，发现一系列烷基膦酸在微波（MW）辐射下与C2-C4醇在[bmim][BF4]存在下可以进行单酯化反应。选择性达到80-98％，而分离收率在61-79％的范围内。所开发的方法是一种绿色的P-酸酯化方法。在M062X/6-311+G(d,p)理论水平上进行的DFT计算（考虑了相应醇的溶剂效应）探索了三步机制，并证明了较高的活化焓（160.6-194.1 kJ·mol-1），只有通过MW辐射才能克服。[bmim][BF4]添加剂的主要作用是增加MW能量的吸收。计算还提出了离子液体中[BF4]阴离子的特定化学作用在另一种机制中的作用。
• Verfahren zur Herstellung von Alkylphosphonsäuren
  申请人：Clariant GmbH

  公开号：EP1061084A1

  公开（公告）日：2000-12-20

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Alkylphosphonsäuren, dadurch gekennzeichnet, daß man Phosphorige Säure (H3PO3) mit kurzkettigen Olefinen umsetzt sowie die Verwendung der nach diesem Verfahren hergestellten Produkte.

  本发明涉及一种制备烷基膦酸的工艺，其特征在于磷酸（H3PO3）与短链烯烃发生反应，并涉及该工艺所得产品的用途。
• US6420598B1
  申请人：——

  公开号：US6420598B1

  公开（公告）日：2002-07-16
• 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.
• Polymer-supported sulfonated magnetic resin: an efficient reagent for esterification of O-alkyl alkylphosphonic-and carboxylic-acids
  作者：Ajay Kumar Purohit、Ajeet Kumar、Varoon Singh、Raghavender Goud D、Rajiv Jain、D.K. Dubey

  DOI：10.1016/j.tetlet.2014.10.086

  日期：2014.12

  A mild and efficient synthetic method has been developed for the esterification of O-alkyl alkylphosphonic-and carboxylic-acids using polymer-supported sulfonated magnetic resins. Polymer-supported resins are recovered using an external magnet and reused several times.

  已经开发了一种温和而有效的合成方法，该方法使用聚合物负载的磺化磁性树脂对O-烷基烷基膦酸和羧酸进行酯化。使用外部磁体回收聚合物负载的树脂，并重复使用几次。