bis-(3,5-di-tert-butyl-2-phenol)-oxamide | 36931-29-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis-(3,5-di-tert-butyl-2-phenol)-oxamide
• 英文别名: 1,2-bis(3,5-di-tert-butyl-2-hydroxyphenyl)oxamide；bis(3,5-di-tert-butyl-2-hydroxyphenyl)oxamide；N,N'-bis(3,5-di-tert-butyl-2-aminophenolic hydroxyl)oxalamide；N,N'-bis(3,5-di-tert-butyl-2-hydroxyphenyl)oxamide；N~1~,N~2~-Bis(3,5-di-tert-butyl-2-hydroxyphenyl)ethanediamide；N,N'-bis(3,5-ditert-butyl-2-hydroxyphenyl)oxamide
• CAS: 36931-29-0
• 化学式: C₃₀H₄₄N₂O₄
• 分子量: 496.69
• InChiKey: NRWOKHUYYGRWBY-UHFFFAOYSA-N

物化性质

• 熔点：
  217 °C
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis-(3,5-di-tert-butyl-2-phenol)-oxamide 、 diethylzinc 以 甲苯 为溶剂， 以91%的产率得到
  参考文献：
  名称：

  Novel hexanuclear and octanuclear zinc alkyl cages derived from a bis-oxamidate ligand

  摘要：

  1 and 2 were prepared by coordination self-assembly from reacting N,N'-bis(3,5-di-tert-buthyl-2-phenol)oxamide (L-H-4) with ZnEt2 in toluene and THF, respectively. The molecular X-ray structures show 1 as an octanuclear Zn-8 cage and 2 as a hexanuclear Zn-6 cage. The nuclearity of these cages is driven by the solvent, in fact 1 gives 2 upon addition of THF. Good polymer conversions for the ROP of rac-lactide were achieved by using 1 and 2 with alcohols as co-catalysts. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2015.12.001
• 作为产物：
  描述：

  3,5-二叔丁基邻苯醌 在 乙二胺 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.5h， 生成 bis-(3,5-di-tert-butyl-2-phenol)-oxamide
  参考文献：
  名称：

  New hexacyclic binuclear tin complexes derived from bis-(3,5-di-tert-butyl-2-phenol)oxamide

  摘要：

  The syntheses of bis-(3,5-di-tert-butyl-2-phenol)oxamide (2a) and four new hexacyclic bimetallic tin compounds derivatives are reported: bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis(dibutyltin) (3), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis(diphenyltin) (4), bis(triethylammonium) bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-(dichlorobutyl-stannate) (5), and bis[(O-Sn) ethanol]-bis-(3, 5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-(chlorophenyltin) (6). All tin compounds show a planar ligand skeleton in which each tin atom is linked to the phenoxy group, to the anilinic nitrogen atom and to the oxygen of the oxamide group. Compounds 3 and 4 have two pentacoordinated diorganyl tin atoms with a distorted bpt geometry, whereas 5 contains a dianionic structure with two hexacoordinated tin atoms bonded to a n-butyl group and to two chlorine atoms and two triethyl ammonium as counterions. Compound 6 has two hexacoordinated tin atoms, each atom is bonded, in addition to the ligand, to one phenyl and one chlorine and coordinated to an ethanol molecule. Characterization of the compounds was made through usual analytical and spectroscopic methods. Structures of 4,6-di-tert-butyl-1-phenol-2-amine 1, the oxamide 2a and the four tin compounds 3-6 were established by the X-ray diffraction analyses. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00689-6

文献信息

• Exchange Interactions and Covalency in Dinuclear Complexes of Iron( <scp>III</scp> ) and Gallium( <scp>III</scp> ) Containing the Redox‐Noninnocent Ligand 1,2‐Bis(3,5‐di‐ <i>tert</i> ‐butyl‐2‐hydroxyphenyl)oxamide
  作者：Udo Beckmann、Eckhard Bill、Thomas Weyhermüller、Karl Wieghardt

  DOI：10.1002/ejic.200200516

  日期：2003.5

  The dinucleating ligand 1,2-bis(3,5-di-tert-butyl-2-hydroxyphenyl)oxamide [H4(bbpo)] has been synthesized. From its reaction with GaCl3 or FeCl3 in CH3OH/NaOH the salts [N(nBu)4]2[MIII2(bbpo)Cl4] [M = Ga (1), Fe (2)] have been isolated as crystalline solids upon addition of [N(nBu)4]Cl. Complexes 1 and 2 have been characterized by single-crystal X-ray crystallography. Cyclic voltammetry established

  已合成双核配体 1,2-双 (3,5-二叔丁基-2-羟基苯基) 草酰胺 [H4(bbpo)]。通过在 CH3OH/NaOH 中与 GaCl3 或 FeCl3 反应，盐 [N(nBu)4]2[MIII2(bbpo)Cl4][M = Ga (1), Fe (2)] 在加入[N(nBu)4]Cl。配合物 1 和 2 已通过单晶 X 射线晶体学表征。循环伏安法确定这两种物质在 CH2Cl2 0.10 M [N(nBu)4]PF6} 中经历了两次连续的、可逆的单电子氧化，显示以配体为中心：一个和两个 N，O 配位的邻亚氨基苯并半醌酸盐形成的 π 自由基与 2 中的高自旋三价铁离子反铁磁耦合。因此，2 的单阴离子具有 St = 1/2 基态。该配合物已通过 Mossbauer、UV/Vis 和 EPR 光谱进行表征。
• Copper and Nickel Complexes of Oxamate−Phenol Containing Ligands: A Structural Dichotomy in Oxidized Species
  作者：Guanqi Wang、Yohann Moreau、Florian Berthiol、Christian Philouze、Olivier Jarjayes、Fabrice Thomas

  DOI：10.1002/ejic.202200781

  日期：——

  The oxamate−phenol association induces a duality in the oxidation locus in the complexes: While the oxidation site would lean toward the metal due to the amide, the ligand would provide a plausible alternative. We establish that the oxidative events are ligand-centered and occur at low potential. Remarkably, phenolates are easier to oxidize than amidophenolates featuring an identical substitution pattern

  草酸盐-苯酚缔合在配合物的氧化位点中引起双重性：虽然氧化位点由于酰胺而倾向于金属，但配体将提供一个合理的选择。我们确定氧化事件以配体为中心并且发生在低电位。值得注意的是，酚盐比具有相同取代模式的氨基酚盐更容易氧化。
• Synthesis, characterization and ethylene polymerization activity of titanium, zirconium and hafnium compounds derivatives from symmetric oxamide
  作者：Marisol Güizado-Rodríguez、Víctor M. Jiménez-Pérez、Jesús E. Hernández-Rivera、J.M. Domínguez、Rosalinda Contreras、Raúl Quijada

  DOI：10.1016/j.poly.2007.05.041

  日期：2007.9

  New non-metallocene polymerization catalysts derived from 1,2-bis(3,5-di-tert-butyl-2-hydroxiphenyl)oxamide (L) and transition metals (Ti, Zr, Ho were synthesized and tested for ethylene polymerization reactions. The syntheses were carried out from various bases and solvents (triethylamine/toluene, NaH/THF and NaOH/methanol). The zirconium compound (5) showed the highest catalytic activity (the polyethylene molecular weight was 98,000 Da) and polydispersity index (1.8-2.0) when n-heptane was used as solvent. In terms of T,, and crystallinity, this catalyst produced the highest density linear polyethylene. (c) 2007 Elsevier Ltd. All rights reserved.
• Hypervalent and binuclear silicon and germanium derivatives from bis-(3,5-di-tert-butyl-2-phenol)-oxamide
  作者：Víctor M. Jiménez-Pérez、Carlos Camacho-Camacho、Ángel Ramos-Organillo、Raúl Ramírez-Trejo、Adrián Peña-Hueso、Rosalinda Contreras、Angelina Flores-Parra

  DOI：10.1016/j.jorganchem.2007.08.042

  日期：2007.12

  The reactions of bis-(3,5-di-tert-butyl-2-phenol)oxamide (1) with Cl2SiR2 (Me or Ph) or Cl2GeR2 (Me, nBu or Ph) in THF provided binuclear pentacoordinated silicon and germanium compounds: bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-dimethylsilane (2), his(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-diphenylsilane (3), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-dimethylgermane (4), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-di-n-butylgermane (5) and bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-diphenylgermane (6). The mono-nuclear tetracoordinated silicon compounds N-acetyl-bis-(3,5-di-tert-butyl-2-oxo-phenyl)-amide-bis-(dimethylsilane) (8) and N-acetyl-bis-(3,5-di-tert-butyl-2-oxo-phenyl)-amide-bis-(diphenylsilane) (9) were synthesized from N-(3,5-di-tert-butyl-2-phenol)acetamide (7) and Cl2SiR2 (R = Me and Ph). Comparison of the Si-29 NMR chemical shifts of the penta- (2 and 3) and tetracoordinated (8 and 9) silicon compounds provided information about the intramolecular coordination of the carbonyl group to the silicon atom. Compounds 3 and 6 were characterized by single-crystal X-ray analyses. They have planar hexacyclic structures where the central atoms present distorted tbp geometries with one nitrogen and two carbon atoms in equatorial positions and two oxygen atoms in apical positions. (C) 2007 Elsevier B.V. All rights reserved.
• Rigid five-coordinate diorganotin derivatives of oxalic acid diamides, studied by 119Sn-NMR and X-ray structural analysis
  作者：Rosalinda Contreras*、Victor M Jimenez-Perez、Carlos Camacho-Camacho、Marisol Güizado-Rodriguez、Bernd Wrackmeyer*

  DOI：10.1016/s0022-328x(00)00254-0

  日期：2000.6

  Bis(2-hydroxy-3, 5-di-tert-butyl-phenylanilido) oxalic acid reacts with diorganotin dichlorides, R2SnCl2, in the presence of triethylamine to give the polycyclic bis(diorganotin) derivatives 1, in which the surroundings of each tin atom correspond to a distorted trigonal bipyramid with one nitrogen and two carbon atoms in the equatorial and two oxygen atoms in the axial positions. The solid state structure was established for la (R = Me) by X-ray analysis, and the agreement between the Sn-119 chemical shift in the solid state and in solution suggests that this structure is retained in solution. It was possible for the first time to determine isotope-induced chemical shifts (1)Delta(12/13)C(Sn-119) for five-coordinate tin nuclei at natural. abundance of C-13. A positive sign of (1)Delta(12/13)C(Sn-119) was found for R = Me (1a), Bu (1b) and Ph (1c). (C) 2000 Elsevier Science S.A. All rights reserved.