1,3-phenylenebis(methylene)bisphosphonic acid tetramethyl ester | 144052-39-1

• 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: 1,3-phenylenebis(methylene)bisphosphonic acid tetramethyl ester
• 英文别名: 1,3-Bis(dimethoxyphosphorylmethyl)benzene
• CAS: 144052-39-1
• 化学式: C₁₂H₂₀O₆P₂
• 分子量: 322.235
• InChiKey: XWZLYENKXBXMDM-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±38.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-phenylenebis(methylene)bisphosphonic acid tetramethyl ester 在 水 作用下， 以 甲醇 为溶剂， 生成 间二甲苯二膦酸
  参考文献：
  名称：

  （邻-羟基苯基）甲基膦酸：其p K a值的合成和电位测定

  摘要：

  从邻-（溴甲基）-或邻-（羟甲基）酚和亚磷酸三烷基酯容易获得（邻-羟基苯基）甲基膦酸。随后的水解产生相应的膦酸。对于一系列此类化合物，p K a值已通过电位计确定。根据电子和空间效应，讨论了它们对芳环中其他取代基的依赖性。

  DOI：

  10.1002/hlca.19930760108
• 作为产物：
  描述：

  1,3-苯二甲醇 、 三甲氧基磷 反应 0.5h， 生成 1,3-phenylenebis(methylene)bisphosphonic acid tetramethyl ester
  参考文献：
  名称：

  （邻-羟基苯基）甲基膦酸：其p K a值的合成和电位测定

  摘要：

  从邻-（溴甲基）-或邻-（羟甲基）酚和亚磷酸三烷基酯容易获得（邻-羟基苯基）甲基膦酸。随后的水解产生相应的膦酸。对于一系列此类化合物，p K a值已通过电位计确定。根据电子和空间效应，讨论了它们对芳环中其他取代基的依赖性。

  DOI：

  10.1002/hlca.19930760108

文献信息

• Synthesis of aryl(difluoromethylenephosphonates) via electrophilic fluorination of α-carbanions of benzylic phosphonates with N-fluorobenzenesulfonimide
  作者：Scott D. Taylor、Christopher C. Kotoris、A.Nicole Dinaut、Mei-Jin Chen

  DOI：10.1016/s0040-4020(97)10395-7

  日期：1998.2

  The electrophilic fluorination of a wide variety of benzylic phosphonates with N-fluorobenzenesulfonimide has been examined. The fluorination reaction proceeds well in the presence of an array of functional groups such as nitro, bromo, ketone, ester, phenyl and ether groups. Phenyl and biphenyl derivatives containing two α,α-difluoromethylenephosphonate groups can also be prepared. This procedure is

  已经研究了多种苄基膦酸酯与N-氟苯磺酰亚胺的亲电子氟化。在一系列官能团如硝基，溴，酮，酯，苯基和醚基的存在下，氟化反应进行得很好。也可以制备含有两个α，α-二氟亚甲基膦酸酯基的苯基和联苯衍生物。该方法与甲基或乙基膦酸酯相容，但是与叔丁基酯或在对位处含有另外的苄基部分的苄基膦酸酯不相容。
• Synthesis of benzylic mono(α,α-difluoromethylphosphonates) and benzylic bis(α,α-difluoromethylphosphonates) via electrophilic fluorination
  作者：Scott D. Taylor、A.Nicole Dinaut、Avinash N. Thadani、Zheng Huang

  DOI：10.1016/0040-4039(96)01847-3

  日期：1996.11

  A series of benzylic mono(α,α-difluoromethylphosphonates) and benzylic bis(α,α-difluoromethylphosphonates) have been prepared via electrophilic fluorination of the corresponding benzylic phosphonates.

  通过相应的苄基膦酸酯的亲电氟化，制备了一系列苄基单（α，α-二氟甲基膦酸酯）和苄基双（α，α-二氟甲基膦酸酯）。
• Phosphonic acid derivatives useful as anti-inflammatory agents
  申请人：THE UPJOHN COMPANY

  公开号：EP0622373A1

  公开（公告）日：1994-11-02

  Novel 1,2-oxaphosphepins are useful as antiinflammatory and antiarthritic agents. A representative oxaphosphepin is 3,4-dihydro-3-methoxy-7-(phenylmethoxy)-1H-naphth[1,8de][1,2]oxaphosphepin-3-oxide.

  小说1,2-氧磷环烷可用作抗炎和抗关节炎药物。代表性的氧磷环烷是3,4-二氢-3-甲氧基-7-(苯甲氧基)-1H-萘[1,8de][1,2]氧磷环烷-3-氧化物。
• Optimization of a Synthetic Arginine Receptor. Systematic Tuning of Noncovalent Interactions
  作者：Stephan Rensing、Markus Arendt、Andreas Springer、Thomas Grawe、Thomas Schrader

  DOI：10.1021/jo0156161

  日期：2001.8.1

  The simple arginine binder I could be optimized by strengthening pi -cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for T-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene - guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.
• Toward Synthetic Adrenaline Receptors:  Strong, Selective, and Biomimetic Recognition of Biologically Active Amino Alcohols by Bisphosphonate Receptor Molecules
  作者：Thomas Schrader

  DOI：10.1021/jo971297v

  日期：1998.1.1

  Xylylene bisphosphonates represent a new class of artificial receptor molecules for alkylammonium ions (Schrader, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2649-2651). Molecular recognition takes place in a 1:1 chelate-binding mode, and an almost ideal array of short, linear hydrogen bonds is created that guarantees maximum electrostatic and hydrogen-bond interactions. The host molecule, which was designed to imitate the natural adrenergic receptor, is selective for 1,2- and 1,3-amino alcohols due to formation of an additional cooperative hydrogen bond between the phosphonate anion and the hydroxyl groups. Biologically important amino alcohols such as glucosamine, 1-aminosorbitol, ephedrine, and the beta-blocker propranolol are bound in DMSO with K-a values between 60 000 and 130 000 M-1. Secondary amines are complexed at least as strongly as their primary counterparts. The phosphonate ester groups allow lateral recognition of the substate. This could be demonstrated for adrenaline model compounds that were recognized by phosphonates carrying extended aromatic ester groups for pi,pi-interactions.