2,2'-dihydroxy-1,1'-binaphthyl-6,6'-bis(phosphonic acid) | 775326-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-dihydroxy-1,1'-binaphthyl-6,6'-bis(phosphonic acid)
• 英文别名: [6-hydroxy-5-(2-hydroxy-6-phosphononaphthalen-1-yl)naphthalen-2-yl]phosphonic acid
• CAS: 775326-94-8；775326-95-9；211055-39-9
• 化学式: C₂₀H₁₆O₈P₂
• 分子量: 446.29
• InChiKey: NNCIOLOREUIUMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  锆酸四丁酯 、 2,2'-dihydroxy-1,1'-binaphthyl-6,6'-bis(phosphonic acid) 以 正丁醇 为溶剂， 以90%的产率得到zirconium(IV) 2,2'-dihydroxy-1,1'-binaphthyl-6,6'-bis(phosphonate) tetrahydrate
  参考文献：
  名称：

  Molecular building block approaches to chiral porous zirconium phosphonates for asymmetric catalysis

  摘要：

  Porous zirconium phosphonates containing chiral dihydroxy functionalities have been synthesized via a building block approach. Enantiopure atropisomeric bisphosphonic acids of various lengths, L-1-L-3, were first synthesized starting from 1,1'-bi-2-naphthol (BINOL) in multi-step sequences. Amorphous chiral porous zirconium phosphonates were then obtained by refluxing BINOL-derived bisphosphonic acids with Zr((OBu)-Bu-n)(4) in n-BuOH, and have been characterized by powder X-ray diffraction, solid-state CP-MAS P-31 NMR, IR, TGA, adsorption measurements, circular dichroism spectroscopy, and microanalyses. These zirconium phosphonates have empirical formulae of (Zr-L1-3).xH(2)O (X = 4 or 5), and exhibit BET surface areas ranging from 431 to 586 m(2)/g. In combination with Ti((OPr)-Pr-i)(4), these zirconium phosphonates have been used to heterogeneously catalyze the additions of diethylzinc to a wide range of aromatic aldehydes with high conversions and e.e. of up to 72%. This work represents a novel approach towards heterogeneous asymmetric catalysis. The tunability of such a molecular building block approach promises to lead to practically useful heterogeneous asymmetric catalytic processes. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2004.01.022
• 作为产物：
  描述：

  6-溴-2-萘酚 在 bis-triphenylphosphine-palladium(II) chloride 2,3,5-三甲基吡啶 、 盐酸 、 三乙基硅烷 、 4-二甲氨基吡啶 、 air 、 三甲基溴硅烷 、 乙基溴化镁 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 82.0h， 生成 2,2'-dihydroxy-1,1'-binaphthyl-6,6'-bis(phosphonic acid)
  参考文献：
  名称：

  Jaffres, Paul-Alain; Bar, Nathalie; Villemin, Didier, Journal of the Chemical Society. Perkin transactions I, 1998, # 13, p. 2083 - 2089

  摘要：

  DOI：

文献信息

• Jaffres, Paul-Alain; Bar, Nathalie; Villemin, Didier, Journal of the Chemical Society. Perkin transactions I, 1998, # 13, p. 2083 - 2089
  作者：Jaffres, Paul-Alain、Bar, Nathalie、Villemin, Didier

  DOI：——

  日期：——
• Molecular building block approaches to chiral porous zirconium phosphonates for asymmetric catalysis
  作者：Helen L. Ngo、Aiguo Hu、Wenbin Lin

  DOI：10.1016/j.molcata.2004.01.022

  日期：2004.6

  Porous zirconium phosphonates containing chiral dihydroxy functionalities have been synthesized via a building block approach. Enantiopure atropisomeric bisphosphonic acids of various lengths, L-1-L-3, were first synthesized starting from 1,1'-bi-2-naphthol (BINOL) in multi-step sequences. Amorphous chiral porous zirconium phosphonates were then obtained by refluxing BINOL-derived bisphosphonic acids with Zr((OBu)-Bu-n)(4) in n-BuOH, and have been characterized by powder X-ray diffraction, solid-state CP-MAS P-31 NMR, IR, TGA, adsorption measurements, circular dichroism spectroscopy, and microanalyses. These zirconium phosphonates have empirical formulae of (Zr-L1-3).xH(2)O (X = 4 or 5), and exhibit BET surface areas ranging from 431 to 586 m(2)/g. In combination with Ti((OPr)-Pr-i)(4), these zirconium phosphonates have been used to heterogeneously catalyze the additions of diethylzinc to a wide range of aromatic aldehydes with high conversions and e.e. of up to 72%. This work represents a novel approach towards heterogeneous asymmetric catalysis. The tunability of such a molecular building block approach promises to lead to practically useful heterogeneous asymmetric catalytic processes. (C) 2004 Elsevier B.V. All rights reserved.