2,4,6-trimethyl benzylphosphonate de diethyle | 63909-52-4

• 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: 2,4,6-trimethyl benzylphosphonate de diethyle
• 英文别名: mesityl-1-methylene-bis(ethylphosphonate)；2.4.6-Trimethylbenzyldiethylphosphonat；Diethyl 2,4,6-Trimethylbenzylphosphonate；2-(diethoxyphosphorylmethyl)-1,3,5-trimethylbenzene
• CAS: 63909-52-4
• 化学式: C₁₄H₂₃O₃P
• 分子量: 270.309
• InChiKey: JISHNMYIBUTGRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  147 °C(Press: 6 Torr)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-trimethyl benzylphosphonate de diethyle 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以90%的产率得到mesityl-1-methylenephosphonic acid
  参考文献：
  名称：

  One, two, and three methylene phosphonic acid groups (–CH2PO3H2) on a mesitylene ring: synthesis, characterization and aspects of supramolecular aggregation

  摘要：

  通过Michaelis-Arbuzov反应后进行酸水解，利用逐步取代三甲苯环上的-CH2Br基团的便利性，以80-90%的产率制备了三甲苯单、双和三甲叉膦酸C6H2Me3(CH2PO3H2)(1)、C6HMe3(CH2PO3H2)2(2)和C6Me3(CH2PO3H2)3(3)。化合物1-4已通过分析和光谱（IR、NMR和MS）技术进行了表征。所有三种化合物的X射线结构研究表明，中心三甲苯环是承载多个甲叉膦酸基团的稳固平台。三甲苯单甲叉膦酸1，可视为受阻的苄基膦酸改性，有趣地通过相邻的-PO3H2基团之间广泛的O-H…O氢键作用形成一维管状结构，尽管由于表面高度疏水性，管间没有这样的相互作用。三甲苯-1,3-二膦酸2的X射线结构显示，分子中-CH2PO3H2呈同向排列，通过广泛的P-OH…O氢键作用形成二维层状结构。三甲苯环同侧存在三个-PO3H2单元导致形成三维框架固体。当前研究清楚地揭示了超分子结构的维数与三甲苯环上膦酸基团数量之间的线性关系。

  DOI：

  10.1039/b9nj00691e
• 作为产物：
  描述：

  2,4,6-三甲基溴化苄 、 亚磷酸三乙酯 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 2,4,6-trimethyl benzylphosphonate de diethyle
  参考文献：
  名称：

  One, two, and three methylene phosphonic acid groups (–CH2PO3H2) on a mesitylene ring: synthesis, characterization and aspects of supramolecular aggregation

  摘要：

  通过Michaelis-Arbuzov反应后进行酸水解，利用逐步取代三甲苯环上的-CH2Br基团的便利性，以80-90%的产率制备了三甲苯单、双和三甲叉膦酸C6H2Me3(CH2PO3H2)(1)、C6HMe3(CH2PO3H2)2(2)和C6Me3(CH2PO3H2)3(3)。化合物1-4已通过分析和光谱（IR、NMR和MS）技术进行了表征。所有三种化合物的X射线结构研究表明，中心三甲苯环是承载多个甲叉膦酸基团的稳固平台。三甲苯单甲叉膦酸1，可视为受阻的苄基膦酸改性，有趣地通过相邻的-PO3H2基团之间广泛的O-H…O氢键作用形成一维管状结构，尽管由于表面高度疏水性，管间没有这样的相互作用。三甲苯-1,3-二膦酸2的X射线结构显示，分子中-CH2PO3H2呈同向排列，通过广泛的P-OH…O氢键作用形成二维层状结构。三甲苯环同侧存在三个-PO3H2单元导致形成三维框架固体。当前研究清楚地揭示了超分子结构的维数与三甲苯环上膦酸基团数量之间的线性关系。

  DOI：

  10.1039/b9nj00691e

文献信息

• Évaluation de l'activité inhibitrice calcique d'une série de benzylphosphonates de diéthyle
  作者：G Tchani、G Baziard-Mouysset、S Younes、J Bellan、M Payard、JL Stigliani、G Grassy、R Bonnafous、J Tisne-Versailles

  DOI：10.1016/0223-5234(92)90120-p

  日期：1992.11

  Thirty-nine diethyl benzylphosphonates related to Fostedil were evaluated as calcium antagonists, using the inhibition test on aortic contraction in the rabbit, which was more selective than the negative inotropic activity test on guinea-pig left atrial muscle. Six compounds were found to have weak activity compared with Fostedil. Structure-activity relationships indicated a certain lipophilic influence; no correlation was found with electronic parameters. The prerequisite structure to obtain active products seems to require 2 conjugated aromatic rings separated by an optimal distance.
• One, two, and three methylene phosphonic acid groups (–CH2PO3H2) on a mesitylene ring: synthesis, characterization and aspects of supramolecular aggregation
  作者：Ramaswamy Murugavel、Mayank Pratap Singh

  DOI：10.1039/b9nj00691e

  日期：——

  The ease of substitution of –CH2Br group on the mesitylene ring in a stepwise manner has been exploited to prepare mesitylene mono-, bis-, and tris-methylene phosphonic acids C6H2Me3(CH2PO3H2) (1), C6HMe3(CH2PO3H2)2 (2), and C6Me3(CH2PO3H2)3 (3) in 80–90% yield, through a Michaelis–Arbuzov reaction followed by acid hydrolysis. Compounds 1–4 have been characterized by analytical and spectroscopic (IR, NMR, and MS) techniques. The X-ray structural investigations on all the three compounds reveal that the central mesitylene ring is a robust platform for hosting multiple methylene phosphonic acid groups. Mesitylene mono-methylene phosphonic acid 1, which can be considered as the sterically encumbered modification of benzyl phosphonic acid, interestingly associates as a one-dimensional tubular structure through extensive O–H⋯O hydrogen bonding between adjacent –PO3H2 groups, albeit with no such interactions between the tubes due to the highly hydrophobic nature of the surface. The X-ray structure of mesitylene-1,3-diphosphonic acid 2 reveals that the molecules exhibit a syn-orientation of the –CH2PO3H2, which are involved in extensive P–OH⋯O hydrogen bonding to result in a two-dimensional layered structure. The presence of three –PO3H2 units on the same side of the mesitylene ring in 3 results in a three-dimensional framework solid. The present studies clearly reveal a linear relationship between the dimensionality of the supramolecular structure and the number of phosphonic acid moieties on the mesitylene ring.

  通过Michaelis-Arbuzov反应后进行酸水解，利用逐步取代三甲苯环上的-CH2Br基团的便利性，以80-90%的产率制备了三甲苯单、双和三甲叉膦酸C6H2Me3(CH2PO3H2)(1)、C6HMe3(CH2PO3H2)2(2)和C6Me3(CH2PO3H2)3(3)。化合物1-4已通过分析和光谱（IR、NMR和MS）技术进行了表征。所有三种化合物的X射线结构研究表明，中心三甲苯环是承载多个甲叉膦酸基团的稳固平台。三甲苯单甲叉膦酸1，可视为受阻的苄基膦酸改性，有趣地通过相邻的-PO3H2基团之间广泛的O-H…O氢键作用形成一维管状结构，尽管由于表面高度疏水性，管间没有这样的相互作用。三甲苯-1,3-二膦酸2的X射线结构显示，分子中-CH2PO3H2呈同向排列，通过广泛的P-OH…O氢键作用形成二维层状结构。三甲苯环同侧存在三个-PO3H2单元导致形成三维框架固体。当前研究清楚地揭示了超分子结构的维数与三甲苯环上膦酸基团数量之间的线性关系。