N,N-Bis-<2,6-Diisopropylphenyl>-oxalimidoylchlorid | 167966-57-6

• 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: N,N-Bis-<2,6-Diisopropylphenyl>-oxalimidoylchlorid
• 英文别名: (2,6-iPr2C6H3)N=C(Cl)-C(Cl)=N(2,6-iPr2C6H3)；Ethanediimidoyl dichloride, bis[2,6-bis(1-methylethyl)phenyl]-；N,N'-bis[2,6-di(propan-2-yl)phenyl]ethanediimidoyl dichloride
• CAS: 167966-57-6
• 化学式: C₂₆H₃₄Cl₂N₂
• 分子量: 445.475
• InChiKey: DZEFONBQNQWQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tributyl(pentafluorophenyl)stannane 、 N,N-Bis-<2,6-Diisopropylphenyl>-oxalimidoylchlorid 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以95%的产率得到N,N′-bis(2,6-diisopropylphenyl)-1,2-bis(pentafluorophenyl)-ethane-1,2-diimine
  参考文献：
  名称：

  碘化铜介导的双（亚胺酰氯）和芳基锡烷合成 α-二亚胺配体

  摘要：

  芳基取代的 α-二亚胺是通过操作简单的碘化铜介导的多氟（氯）芳基三丁基锡烷和双（亚胺酰氯）之间的 Stille 型偶联制备的。反应在商业级N,N-二甲基甲酰胺 (DMF) 溶剂中在 70 °C 下进行，不需要添加剂或碱。对于芳环上具有两个或多个氟或氯取代基的芳基锡烷，偶联是成功的。产品以中等到良好的收率获得。这种方法允许简单合成可能用于烯烃聚合以及其他催化转化的 α-二亚胺配体。

  DOI：

  10.1021/acs.organomet.2c00264
• 作为产物：
  描述：

  N,N’-2,6-diisopropylphenyl-oxamide 在 五氯化磷 作用下， 以 甲苯 为溶剂， 以48%的产率得到N,N-Bis-<2,6-Diisopropylphenyl>-oxalimidoylchlorid
  参考文献：
  名称：

  Zur Aminolyse von Bis-Imidoylchloriden der Oxals�ure. I. Umsetzung mit aromatischen und aliphatischen Aminen

  摘要：

  The reaction between bis-imidoylchlorides 2 derived from oxalic acid and several aromatic and aliphatic amines was investigated. While primary aromatic amines need a thermical activation by refluxing, primary aliphatic amines give mainly at room temperature the amidines 3 in moderatly up to good yields.Proceeding from enantiomeric pure amines e.g. (R)- or (S)-1-phenethylamine the new homochiral oxalic amidines 3y and 3z with C-2-symmetry were obtained. Several secondary amines react with the bis-imidoylchloride 2a to give via intramolecular cycloacylation derivatives of isatine. The new synthesized amidines 3 perform systems with a strong molecular dynamic like prototropie and E/Z-interconversion. All new compounds described were characterized by elemental analysis and spectroscopic methods.

  DOI：

  10.1002/prac.19953370130

文献信息

• Investigations into the reactivity of lithium indenyl with alpha diimines with chlorinated backbones and formation of related functional ligands and metal complexes
  作者：Chi-Tien Chen、Mark E. Fischer、Caroline Windsor、Ino C. Vei、David G. Calatayud、Malcolm L.H. Green、Sofia I. Pascu

  DOI：10.1016/j.poly.2016.09.021

  日期：2016.11

  and a chlorine substituted alpha diimine of the form [Cl(NPh)2}C)]2 unexpectedly yielded the corresponding NH rearranged derivative [PhN(H)C(C9H6)]2 (1) rather than the predicted symmetrical α-diimine. This compound 1 was characterised by 1H NMR, 13C1H} NMR and mass spectrometry, and additionally by X-ray diffraction. It was found that 1 was the first indene-substituted and symmetric secondary amine

  摘要茚基锂与[Cl（NPh）2} C）] 2形式的氯取代的α二亚胺之间的反应出乎意料地产生了相应的NH重排衍生物[PhN（H）C（C9H6）] 2（1），而不是预测对称的α-二亚胺。该化合物1通过1 H NMR，13 C 1H} NMR和质谱以及另外通过X射线衍射进行表征。发现1是第一个被茚取代的对称仲胺，它在DMSO中也具有很高的荧光性。已经研究了1对基于MX2片段的简单无机和有机金属过渡金属前体的反应性，其中M =第10组金属，X =卤化物或甲基。出奇，与[PtMe2（COD）]的反应导致在C–C配体主链上结合的茚基与新配体（2）之间的偶联反应被发现，试图合成金属连接的二胺。单晶X射线衍射研究证实了该化合物2在固态下具有耦合的茚基残基和离域的C-C键。通过X射线晶体学进行的结构鉴定表明，化合物2是非常稀少的扁平和扩展的芳族有机分子的实例，通过质谱和质谱分析，红外光谱和核磁共振光谱可
• The Synthesis of Carboxy- and Cyano-substituted 4H-Imidazoles: Redoxactive Ligands as Starting Materials for Metal-Metal Multiply Bonded Compounds and Heterobimetallic Complexes
  作者：Martin Matschke、Jorg Blumhoff、Rainer Beckert、Wolfgang Imhof

  DOI：10.1515/znb-2009-0606

  日期：2009.6.1

  Cyanobenzoic acids proved to be suitable starting materials for the transformation into multifunctional products of the 4H-imidazole type. Employing two different pathways, the new derivatives 1b-d which possess carboxy/cyano groups were synthesized. In addition, derivative 1d formed the basis for the construction of novel bis-4H-imidazoles with two different complexation spheres. The structures of

  氰基苯甲酸被证明是转化为 4H-咪唑型多功能产品的合适起始原料。采用两种不同的途径，合成了具有羧基/氰基的新衍生物 1b-d。此外，衍生物 1d 是构建具有两种不同络合球体的新型双 4H-咪唑的基础。所有新衍生物的结构均通过核磁共振光谱、质谱、元素分析、紫外/可见/荧光光谱和电化学测量证实。图形摘要羧基和氰基取代的 4H-咪唑的合成：氧化还原活性配体作为金属-金属多键化合物和异双金属配合物的起始材料
• Zur Aminolyse von Bis-Imidoylchloriden der Oxals�ure. I. Umsetzung mit aromatischen und aliphatischen Aminen
  作者：Dirk Lindauer、Rainer Beckert、Manfred D�ring、Peer Fehling、Helmar G�rls

  DOI：10.1002/prac.19953370130

  日期：——

  The reaction between bis-imidoylchlorides 2 derived from oxalic acid and several aromatic and aliphatic amines was investigated. While primary aromatic amines need a thermical activation by refluxing, primary aliphatic amines give mainly at room temperature the amidines 3 in moderatly up to good yields.Proceeding from enantiomeric pure amines e.g. (R)- or (S)-1-phenethylamine the new homochiral oxalic amidines 3y and 3z with C-2-symmetry were obtained. Several secondary amines react with the bis-imidoylchloride 2a to give via intramolecular cycloacylation derivatives of isatine. The new synthesized amidines 3 perform systems with a strong molecular dynamic like prototropie and E/Z-interconversion. All new compounds described were characterized by elemental analysis and spectroscopic methods.
• 4H-Imidazoles as functional dyes: synthesis of bichromophores and extension of the merocyanine system
  作者：Martin Matschke、Jörg Blumhoff、Rainer Beckert

  DOI：10.1016/j.tet.2008.05.117

  日期：2008.8

  A series of bichromophores consisting of a 'classical' chromophore and 4H-imidazoles were synthesized starting from appropriate cyano and carboxy functionalized systems. In their UV-vis spectra, an additive absorption of both chromophores was detected making them wide range-absorbing dyes. In addition, new properties as redox activity, pH-switchability and metal-chelating substructures are newly introduced into the molecules. In order to achieve more bathochromic absorbing systems, the chromophore of 4H-imidazoles was extended. The 4H-imidazo-[1,2-a]-pyridines, which are easily accessible by cyclization of 2-aminopyridines with bis-imidoylchlorides, show long wavelength absorptions up to 616 nm. Their reduction reversibly yields yellow, blue fluorescent 1-azaindolizines. In contrast to leucoforms reduction products show a high stability towards oxygen and could only forms of 4H-imidazoles, be reoxidized to their starting materials by oxidation agents, such as DDQ. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and structural investigations of Ni(II)- and Pd(II)-coordinated α-diimines with chlorinated backbones
  作者：Sofia I. Pascu、Gabor Balazs、Jennifer C. Green、Malcolm L.H. Green、Ino C. Vei、John E. Warren、Caroline Windsor

  DOI：10.1016/j.ica.2009.11.009

  日期：2010.4

  Novel square planar Pd(II) alpha-diimines [PdX2ArN=C(Cl)}(2)], where Ar = C6H5, (2,6-Me2C6H3), (2,6-(Pr2C6H3)-Pr-i) and X = Cl or Br, and the octahedral Ni(II) complex [NiBr2(C6H5)N=C(Cl)}(2)(THF)(2)] have been prepared and characterised by spectroscopic methods. For two of the Pd(II) complexes and the Ni(II) complex the crystal structures were determined by X-ray crystallography. A further insight into the geometry and electronic structure of [PdBr2(2,6-Me2C6H3)N=C(Cl)}(2)] was gained using density functional theoretical calculations (DFT). This compound resembles structurally and electronically typical olefin polymerisation pre-catalysts supported by alpha-diimines incorporating methyl-and 1,8-naphtalenyl substituents at the ligand backbone. The chlorine-substituted backbone of the free ligand [2,6-Me2C6H3N=C(Cl)](2) can be employed in further alkylation reactions to generate new multifunctional ligand prototypes with potential uses as ansa-metallocene/diimines building blocks for catalytic applications of heterobimetallic complexes. (C) 2009 Elsevier B.V. All rights reserved.