2,3-bis[N,N-(2,4-dimethylphenyl)imino]butane | 49673-38-3

• 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: 2,3-bis[N,N-(2,4-dimethylphenyl)imino]butane
• 英文别名: N,N'-butane-2,3-diylidenebis(2,4-dimethylaniline)；N,N'-bis(2,4-dimethylbenzene)-2,3-dimethyl-1,4-butadiene；2,4-Me2D；(Z)-N-[(Z)-3-(2,4-Dimethylphenylimino)butan-2-ylidene]-2,4-dimethylaniline；2-N,3-N-bis(2,4-dimethylphenyl)butane-2,3-diimine
• CAS: 49673-38-3
• 化学式: C₂₀H₂₄N₂
• 分子量: 292.424
• InChiKey: HBQMEWSZPHWNPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  乙二醇二甲醚溴化镍 、 2,3-bis[N,N-(2,4-dimethylphenyl)imino]butane 以 二氯甲烷 为溶剂， 反应 18.0h， 以86%的产率得到[Ni₃(μ²-Br)₃(μ³-Br)₂([(2,4-Me₂C₆H₃)NC(Me)]₂)₃]*Br
  参考文献：
  名称：

  具有α-二亚胺配体的自支撑环状三核镍（0）配合物催化的炔烃的环三聚化†

  摘要：

  环状三核α-二亚胺镍（0）络合物[{Ni（μ- LMe -2,4）} 3 ]（2）是由“预组织”的三聚LNiBr 2型三方前体[倪3（μ 2 -Br）3（μ 3 -Br）2（L ME-2,4）3 ]·能Br（1 ; l ME-2,4 = [（2,4--ME 2 ç 6 ħ 3）NC（Me）] 2）。在配合物2中，α-二亚胺配体不仅表现出正常的N，N'-螯合模式，但它们也通过C N键与Ni的不寻常π配位而充当Ni原子之间的桥梁。配合物2能够催化炔烃的环三聚反应以形成高产率和对1,3,5-异构体的区域选择性的取代苯，这随所用炔烃的性质而变化。该络合物代表一种方便的自支撑镍（0）催化剂，不需要其他配体和还原剂。

  DOI：

  10.1039/c9dt00819e
• 作为产物：
  描述：

  2,3-丁二酮 、 2,4-二甲基苯胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 40.0h， 生成 2,3-bis[N,N-(2,4-dimethylphenyl)imino]butane
  参考文献：
  名称：

  New α-diimine nickel complexes—Synthesis and catalysis of alkene oligomerization reactions

  摘要：

  Three alpha-diimine complexes of Ni-II of the general formula {2,3-bis[N,N-(aryl)imino]butane}NiBr2 with aryl groups 2,3,5,6-F-4-C6H, 2-CF3-C6H4 and 2,4-(CH3)(2)-C6H3 were synthesized and used as catalyst precursors in oligomerization reactions of ethylene and propylene. Oligomerization catalysts were produced by activating the complexes with AlEt2Cl, Al2Et3Cl3, and with combinations of these compounds and PPh3. The catalysts convert ethylene into low molecular-weight materials (liquids and waxes) with oligomer chains containing 15-20 mol.% of methyl branches and 4-6 mol.% of ethyl branches, which are apparently produced in "chain-walking" reactions of active centers along oligomer chains. Oligomerization of propylene yields a variety of light products, mostly dimers, which are formed in primary and secondary insertion reactions of propylene into Ni-H and Ni-C bonds in active centers. Reaction schemes of oligomer formation are discussed. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2016.07.024

文献信息

• One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts
  作者：Dmitry V. Pasyukov、Maxim A. Shevchenko、Konstantin E. Shepelenko、Oleg V. Khazipov、Julia V. Burykina、Evgeniy G. Gordeev、Mikhail E. Minyaev、Victor M. Chernyshev、Valentine P. Ananikov

  DOI：10.1002/anie.202116131

  日期：2022.2.21

  and imidazolinium salts in one step via cascade reactions of easily available 1,4-diaza-1,3-butadienes with trialkyl orthoformates and heteroatomic nucleophiles was developed. Feasibility of the new imidazol(in)ium salts for direct metallation to give M/NHC complexes (M=Pd, Ni, Cu, Ag, Au) was demonstrated.

  开发了一种通过容易获得的1,4-二氮杂-1,3-丁二烯与原甲酸三烷基酯和杂原子亲核试剂的级联反应一步合成多种杂原子官能化咪唑鎓和咪唑啉鎓盐的新策略。证明了新的咪唑（in）鎓盐直接金属化以产生 M/NHC 配合物（M=Pd、Ni、Cu、Ag、Au）的可行性。
• Re(I)(tricarbonyl)(carboxylate) complexes with the [N,N′-bis(2,4,6-trimethylbenzene)-1,4-diazabutadiene] (2,4,6-Me3G) and [N,N′-bis(2,4-dimethylbenzene)-2,3-dimethyl-1,4-diazabutadiene] (2,4-Me2D) ligands – Syntheses and spectroscopic studies. The crystal structure of [Re(CO)3(2,4,6-Me3G)(OCOCF3)]
  作者：Reza Kia、Valiollah Mirkhani、Alajos Kálmán、Andrea Deák

  DOI：10.1016/j.poly.2007.01.043

  日期：2007.7

  Two new carboxylato complexes, [Re(CO)(3)(DAB)(OCOCF3)] (DAB = substituted aromatic diazabutadiene ligands), were prepared by the reaction of [Re(CO)5CL] with the DAB ligands, and the subsequent reaction with AgOCOCF3 gave the related carboxylate complexes. These new complexes were characterized by FTIR, NMR, UV-Vis spectra and elemental analysis. In both complexes, the Re atom has a distorted octahedral configuration and is coordinated by two carbonyl groups and the diimine group of the organic ligand in the equatorial plane. Octahedral coordination is completed at the axial positions by another carbonyl ligand and a carboxyl 0 atom of the trifluoroacetate anion. Electrochemical behaviour of the investigated complexes has been studied by cyclic voltanimetry. (C) 2007 Elsevier Ltd. All rights reserved.
• Cyclotrimerization of alkynes catalyzed by a self-supported cyclic tri-nuclear nickel(0) complex with α-diimine ligands
  作者：Lingyi Shen、Yanxia Zhao、Qiong Luo、Qian-Shu Li、Bin Liu、Carl Redshaw、Biao Wu、Xiao-Juan Yang

  DOI：10.1039/c9dt00819e

  日期：——

  α-diimine nickel(0) complex [Ni(μ-LMe-2,4)}3] (2) was synthesized from a “pre-organized”, trimerized trigonal LNiBr2-type precursor [Ni3(μ2-Br)3(μ3-Br)2(LMe-2,4)3]·Br (1; LMe-2,4 = [(2,4-Me2C6H3)NC(Me)]2). In complex 2, the α-diimine ligands not only exhibit the normal N,N′-chelating mode, but they also act as bridges between the Ni atoms through an unusual π-coordination of a CN bond to Ni. Complex 2 is

  环状三核α-二亚胺镍（0）络合物[Ni（μ- LMe -2,4）} 3 ]（2）是由“预组织”的三聚LNiBr 2型三方前体[倪3（μ 2 -Br）3（μ 3 -Br）2（L ME-2,4）3 ]·能Br（1 ; l ME-2,4 = [（2,4--ME 2 ç 6 ħ 3）NC（Me）] 2）。在配合物2中，α-二亚胺配体不仅表现出正常的N，N'-螯合模式，但它们也通过C N键与Ni的不寻常π配位而充当Ni原子之间的桥梁。配合物2能够催化炔烃的环三聚反应以形成高产率和对1,3,5-异构体的区域选择性的取代苯，这随所用炔烃的性质而变化。该络合物代表一种方便的自支撑镍（0）催化剂，不需要其他配体和还原剂。
• New α-diimine nickel complexes—Synthesis and catalysis of alkene oligomerization reactions
  作者：Laura A. Rishina、Yury V. Kissin、Svetlana S. Lalayan、Svetlana C. Gagieva、Dmitri A. Kurmaev、Vladislav A. Tuskaev、Boris M. Bulychev

  DOI：10.1016/j.molcata.2016.07.024

  日期：2016.11

  Three alpha-diimine complexes of Ni-II of the general formula 2,3-bis[N,N-(aryl)imino]butane}NiBr2 with aryl groups 2,3,5,6-F-4-C6H, 2-CF3-C6H4 and 2,4-(CH3)(2)-C6H3 were synthesized and used as catalyst precursors in oligomerization reactions of ethylene and propylene. Oligomerization catalysts were produced by activating the complexes with AlEt2Cl, Al2Et3Cl3, and with combinations of these compounds and PPh3. The catalysts convert ethylene into low molecular-weight materials (liquids and waxes) with oligomer chains containing 15-20 mol.% of methyl branches and 4-6 mol.% of ethyl branches, which are apparently produced in "chain-walking" reactions of active centers along oligomer chains. Oligomerization of propylene yields a variety of light products, mostly dimers, which are formed in primary and secondary insertion reactions of propylene into Ni-H and Ni-C bonds in active centers. Reaction schemes of oligomer formation are discussed. (C) 2016 Elsevier B.V. All rights reserved.