3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid
• 英文别名: (3,5-Ditert-butyl-2-hydroxyphenyl)methylphosphonic acid
• 化学式: C₁₅H₂₅O₄P
• 分子量: 300.335
• InChiKey: STIQUENVEUMJJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cadmium(II) perchlorate hexahydrate 、 2,2'-联吡啶 、 3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid 以 甲醇 为溶剂， 反应 25.0h， 以85%的产率得到[Cd(3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid)2(2,2'-bipyridine)2]*(3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid)
  参考文献：
  名称：

  Mono and dinuclear group 12 phosphonates derived from a sterically encumbered phosphonic acid: Observation of esterification

  摘要：

  Metal phosphonates [Zn-2(dtbhp)(2)(TMEDA)(2)(H2O)(2)]center dot 0.5CH(3)CN (1), Cd-2(dtbhp)(2)(TMEDA)(2)(H2O)(2)]center dot 0.5CH(3)CN (2), [Cd-2(mdtbhp)(2)(1,10-phenanthroline)(4)]center dot(ClO4)(2)(CH3OH)(2) (3), and [Cd(dtbhp-H)(2)(2,2'-bpy)(2)](dtbhp-H-2) (4) have been synthesized at room temperature from a reaction between a suitable metal precursor, 3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid (dtbhp-H-2) and an ancillary ligand, tetramethylenethylene diamine (TMEDA), 1,10-phenanthroline and 2,2'-bipyridine; Single crystal X-ray structure determination reveals that compound 1 crystallizes in the orthorhombic Fdd2 space group, while compounds 3 and 4 crystallize in the triclinic P (1) over bar space group. A rare P-O-H bond esterification is observed in compound 3, presumably catalyzed by perchloric acid formed in the reaction. Compounds 1-3 are discrete dinuclear complexes while monomeric complex 4 forms a ID polymeric chain through extended intermolecular hydrogen bonding, aided by free P-OH and P=O groups of the coordinated as well as the lattice phosphonic acid. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.05.011
• 作为产物：
  描述：

  2,4-二叔丁基苯酚 在 盐酸 、 水 、 lithium hydroxide 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid
  参考文献：
  名称：

  Mono and dinuclear group 12 phosphonates derived from a sterically encumbered phosphonic acid: Observation of esterification

  摘要：

  Metal phosphonates [Zn-2(dtbhp)(2)(TMEDA)(2)(H2O)(2)]center dot 0.5CH(3)CN (1), Cd-2(dtbhp)(2)(TMEDA)(2)(H2O)(2)]center dot 0.5CH(3)CN (2), [Cd-2(mdtbhp)(2)(1,10-phenanthroline)(4)]center dot(ClO4)(2)(CH3OH)(2) (3), and [Cd(dtbhp-H)(2)(2,2'-bpy)(2)](dtbhp-H-2) (4) have been synthesized at room temperature from a reaction between a suitable metal precursor, 3,5-di-tert-butyl-2-hydroxybenzylphosphonic acid (dtbhp-H-2) and an ancillary ligand, tetramethylenethylene diamine (TMEDA), 1,10-phenanthroline and 2,2'-bipyridine; Single crystal X-ray structure determination reveals that compound 1 crystallizes in the orthorhombic Fdd2 space group, while compounds 3 and 4 crystallize in the triclinic P (1) over bar space group. A rare P-O-H bond esterification is observed in compound 3, presumably catalyzed by perchloric acid formed in the reaction. Compounds 1-3 are discrete dinuclear complexes while monomeric complex 4 forms a ID polymeric chain through extended intermolecular hydrogen bonding, aided by free P-OH and P=O groups of the coordinated as well as the lattice phosphonic acid. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.05.011

文献信息

• (<i>o</i>-Hydroxyphenyl)methylphosphonic acids: Synthesis and potentiometric determinations of their p<i>K</i>_aValues
  作者：Volker Böhmer、Walter Vogt、Salah Chafaa、Jean Meullemeestre、Marie-José Schwing、François Vierling

  DOI：10.1002/hlca.19930760108

  日期：1993.2.10

  (o-Hydroxyphenyl)methylphosphonic acids are readily obtained from o-(bromomethyl)- or o-(hydroxymethyl)phenols and trialkyl phosphites. Subsequent hydrolysis leads to the corresponding phosphonic acids. For a series of such compounds, the pKa values have been determined by potentiometry. Their dependence on additional substituents in the aromatic ring is discussed in terms of electronic and steric

  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。