5-(2-hydroxyphenyl)-10,15,20-triphenylporphyrin zinc(II) | 503092-01-1

• 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: 5-(2-hydroxyphenyl)-10,15,20-triphenylporphyrin zinc(II)
• 英文别名: 5-(2-hydroxyphenyl)-10,15,20-tris(phenyl) zinc(II) porphyrin
• CAS: 503092-01-1
• 化学式: C₄₄H₂₈N₄OZn
• 分子量: 694.123
• InChiKey: QNUTUYQSXSRINP-RLPATYCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.28
• 重原子数：
  50.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.21
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyphenyl)-10,15,20-triphenylporphyrin zinc(II) 、 3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl phosphorochloridite 在 diisopropylethylamine 作用下， 以 甲苯 为溶剂， 以46%的产率得到(3,3'-5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)(5-(phenyl-2-yl)-10,15,20-tris(phenyl) zinc(II) porphyrin)phosphite
  参考文献：
  名称：

  Supraphos: A supramolecular strategy to prepare bidentate ligands

  摘要：

  Herein, we report a new strategy for the preparation of chelating bidentate ligands, which involves the mixing of two triondentate ligands functionalized with complementary binding sites. The assembly process is based on selective metal-ligand interactions employing phosphite zinc(II) porphyrins 1-6 and the nitrogen-containing phosphorus ligands b-i (Scherne 1). Only 14 monodentate ligands were utilized to generate a library of 48 palladium catalysts based on supraphos-type bidentate ligands. The characterization of rhodium complexes based on representative Supramolecular bidentate ligands and the comparison of their performance in the hydroformylation of styrene will be presented. The current library of catalysts was tested in the asymmetric palladium-catalyzed alkylation of rac-1,3-diphenyl-2-propenyl acetate, which resulted in a large variety in the observed enantioselectivity for the different catalysts. Importantly, small variations in the supraphos building blocks, lead to large differences in the enantioselectivity imposed by the catalyst, the most selective catalyst producing 97% ee. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.02.026

文献信息

• Synthesis of Building Blocks for the Development of the SUPRAPhos Ligand Library and Examples of Their Application in Catalysis
  作者：P. Elsbeth Goudriaan、Xiao-Bin Jang、Mark Kuil、Renske Lemmens、Piet W. N. M. Van Leeuwen、Joost N. H. Reek

  DOI：10.1002/ejoc.200800499

  日期：2008.12

  which widens the scope for application in asymmetric homogeneous catalysis. For example, we report the synthesis of phosphorus amidite appended porphyrins and building blocks with stereogenic centers at the phosphorus. With the new building blocks described in this paper we can form a 450-membered SUPRAPhos library, which is based on 45 building blocks (30 pyridyl phosphorus ligands and 15 complementary

  我们之前已经介绍了 SUPRAPhos 配体库，它基于通过氮-锌相互作用自组装的组件，并在此报告了该库的扩展，它扩大了在不对称均相催化中的应用范围。例如，我们报告了磷酰胺附加卟啉和在磷上具有立体中心的结构单元的合成。使用本文中描述的新构建块，我们可以形成一个 450 成员的 SUPRAPhos 库，该库基于 45 个构建块（30 个吡啶基磷配体和 15 个互补的卟啉附加磷配体）。包括在铑催化的苯乙烯不对称加氢甲酰化中使用库成员的实例。
• Supraphos:  A Supramolecular Strategy To Prepare Bidentate Ligands
  作者：Vincent F. Slagt、Marc Röder、Paul C. J. Kamer、Piet W. N. M. van Leeuwen、Joost N. H. Reek

  DOI：10.1021/ja038955f

  日期：2004.4.1

  We report a new strategy for the preparation of chelating bidentate ligands, which involves just the mixing of two monodentate ligands functionalized with complementary binding sites. In the current example, the assembly process is based on selective metal-ligand interactions, using phosphite zinc(II) porphyrins 1-6 and the nitrogen donor ligands b-i. From only 16 monodentate ligands, a library of 60 palladium catalysts based on 48 bidentate ligand assemblies has been prepared. The relatively small catalyst library gave a large variety in the selectivity of the alkylation of rac-1,3-diphenyl-2-propenyl acetate. Importantly, small variations in the building blocks lead to large differences in the enantioselectivity imposed by the catalyst (up to 97% ee).