N,N'-bis(2-isopropylphenyl)-2,3-butanediimine | 49673-33-8

• 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-isopropylphenyl)-2,3-butanediimine
• 英文别名: 2-N,3-N-bis(2-propan-2-ylphenyl)butane-2,3-diimine
• CAS: 49673-33-8
• 化学式: C₂₂H₂₈N₂
• 分子量: 320.478
• InChiKey: KPGCGAPVFNUJQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  83 °C
• 沸点：
  447.1±48.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  N,N'-bis(2-isopropylphenyl)-2,3-butanediimine 在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 17.0h， 生成 1,3-bis(2-isopropylphenyl)-4,5-dimethyl-imidazolium tetrafluoroborate
  参考文献：
  名称：

  C 2 -对称阻转异构体N-杂环卡宾-钯(II)配合物：合成、手性拆分以及在酰胺对映选择性α-芳基化中的应用

  摘要：

  阻转异构N-杂环卡宾(NHC)-金属配合物的概念被扩展到具有C 2对称性的NHC，并用于制备钯基配合物。对 NHC 前体的深入研究和各种 NHC 配体的筛选使我们能够规避与内消旋复合物形成相关的问题。制备了一组 8 种阻转异构体 NHC-钯配合物，并通过手性 HPLC 在制备规模上进行有效拆分，获得了高对映体纯度。这些配合物在酰胺的分子内 α-芳基化中表现出良好的活性，并且以优异的对映选择性（高达 98% ee）分离出各种环状产物。

  DOI：

  10.1039/d3dt01182h
• 作为产物：
  描述：

  2,3-丁二酮 、 2-异丙基苯胺 在 甲酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90.5%的产率得到N,N'-bis(2-isopropylphenyl)-2,3-butanediimine
  参考文献：
  名称：

  含α-二亚胺配体的钴(II)配合物催化1,3-丁二烯的高活性顺式1,4选择性聚合

  摘要：

  合成了一系列带有α-二亚胺配体的钴（II）配合物，并通过元素和光谱分析对其进行了表征。这些配合物的通式为 [ArN = C(Me)-(Me)C = NAr]CoCl2 (Ar = C6H5, 3a; 4-MeC6H4, 3b; 4-MeOC6H4, 3c; 4-FC6H4, 3d; 4-ClC6H4 , 3e; 2-MeC6H4, 3f; 2-EtC6H4, 3g; 2-iPrC6H4, 3h; 2, 4, 6-Me3C6H2, 3i; 2, 6-Et2C6H3, 3j; 2, 6-iPrC6H3). 还合成了 2,6-双[(2,6-二异丙基苯基亚氨基)乙基]吡啶 CoCl2 (4a) 以进行比较。通过X射线晶体学进一步分析了配合物3i、3k和4a的结构。当 Co(II) 配合物用倍半氯化乙基铝活化时，它们对 1,3-丁二烯聚合表现出很高的催化活性。生产的聚合物具有高顺 1,4 立体规整度（高达

  DOI：

  10.1016/s1872-2067(12)60625-1

文献信息

• Trans- andcis- Cobalt(III), Iron(III), and Chromium(III) Complexes Based on α- and γ-Diimine Schiff Base Ligands: Synthesis and Evaluation of the Complexes as Catalysts for Oxidation of L-Cysteine
  作者：Adnan S. Abu-Surrah、Hamzeh M. Abdel-Halim、Feda'a M. Al-Qaisi

  DOI：10.1002/zaac.200700578

  日期：2008.5

  The synthesis of a new series of trans and racemic cis isomers of cobalt(III)-, iron(III)-, and chromium(III)-based complexes with the α- and γ-diimine Schiff base ligands, N,N′-bis(X)-2,3-butandiimine and N,N′-bis(X)-1,2-phenyldiimine (X = cyclohexyl, 2-isopropylphenyl, 1-naphthyl) is described. To confirm the identity of the complexes prepared in the present study, a variety of techniques including

  合成一系列新的钴 (III)-、铁 (III)- 和铬 (III) 基配合物与 α- 和 γ-二亚胺席夫碱配体 N,N'- 的反式和外消旋顺式异构体描述了双(X)-2,3-丁二亚胺和N,N'-双(X)-1,2-苯基二亚胺（X = 环己基、2-异丙基苯基、1-萘基）。为了确认本研究中制备的复合物的身份，使用了多种技术，包括元素分析、磁化率、红外、质谱 (EI) 和紫外/可见光谱。一些分离的配合物已被评估为 L-半胱氨酸氧化的催化剂。初步结果表明，金属原子、配合物的几何形状、辅助取代基和配体的骨架影响了氧化反应的速率。
• Interionic Structure of Ion Pairs and Ion Quadruples of Half-Sandwich Ruthenium(II) Salts Bearing α-Diimine Ligands
  作者：Daniele Zuccaccia、Gianfranco Bellachioma、Giuseppe Cardaci、Gianluca Ciancaleoni、Cristiano Zuccaccia、Eric Clot、Alceo Macchioni

  DOI：10.1021/om7003157

  日期：2007.7.30

  The interionic structure of complexes [Ru(eta(6)-Arene)(2-R-C6H4)N = C(Me)-C(Me)= N(2-R-C6H4)}Cl]X was investigated by an integrated experimental (PGSE diffusion and NOE NMR spectroscopy and X-ray single-crystal studies) and theoretical (DFT and ONIOM calculations) approach. PGSE NMR experiments indicated that ion pairing is the main aggregative process in CD2Cl2 and solvents with higher relative permittivity. They also showed that the tendency to ion pairing for isodielectric solvents is higher when the latter are protic. NOE interionic contacts were observed in 2-propanol-d(8) even for BARF(-) salts. Ion pairing was favored by more coordinating counterions and an increase in concentration. An equilibrium between ion pairs and ion quadruples was observed by PGSE measurements in chloroform-d and benzene-d(6). Such equilibrium is shifted toward ion quadruples by an increase in the concentration or when least coordinating counterions are used. For small fluorinated counterions, NOE studies located the anion in ion pairs above the plane containing the C = N imine moieties. ONIOM calculations found that this anion-cation orientation was at least 35.9 kJ/mol lower in energy than a second orientation with the anion close to cymene, which, in some cases, was observed in the solid state. NOE investigations on complexes with BPh4- counterion did not allow a single orientation capable of explaining the observed NOEs to be found. X-ray studies showed that one cation is surrounded by two anions. ONIOM calculations found that these two anion-cation orientations have similar energies. X-ray and NOE NMR data strongly suggest that ion quadruples with BPh4- anions are constituted by an alternation of cations and anions. Interionic NOE intensities are almost invariant on passing from ion pairs to ion quadruples with small fluorinated counterions. X-ray studies suggested at least four possible structures of ion quadruples differing in both disposition and orientation of the ionic moieties. Three structures considered by ONIOM calculations were similar in energy, but more stable than the separated ion pairs.
• Highly active and cis-1,4 selective polymerization of 1,3-butadiene catalyzed by cobalt(II) complexes bearing α-diimine ligands
  作者：Xiangyu Jia、Heng Liu、Yanming Hu、Quanquan Dai、Jifu Bi、Chenxi Bai、Xuequan Zhang

  DOI：10.1016/s1872-2067(12)60625-1

  日期：2013.8

  synthesized for comparison. The structures of complexes 3i, 3k, and 4a were further analyzed by X‐ray crystallography. When the Co(II) complexes were activated with ethylaluminum sesquichloride, they exhibited high catalytic activity for 1,3‐butadiene polymerization. The polymers produced have high cis‐1,4 stereoregularity (up to 98.0%) and high molecular weights (Mn = 1×10^4 - 1×10^5). The substituent ligand

  合成了一系列带有α-二亚胺配体的钴（II）配合物，并通过元素和光谱分析对其进行了表征。这些配合物的通式为 [ArN = C(Me)-(Me)C = NAr]CoCl2 (Ar = C6H5, 3a; 4-MeC6H4, 3b; 4-MeOC6H4, 3c; 4-FC6H4, 3d; 4-ClC6H4 , 3e; 2-MeC6H4, 3f; 2-EtC6H4, 3g; 2-iPrC6H4, 3h; 2, 4, 6-Me3C6H2, 3i; 2, 6-Et2C6H3, 3j; 2, 6-iPrC6H3). 还合成了 2,6-双[(2,6-二异丙基苯基亚氨基)乙基]吡啶 CoCl2 (4a) 以进行比较。通过X射线晶体学进一步分析了配合物3i、3k和4a的结构。当 Co(II) 配合物用倍半氯化乙基铝活化时，它们对 1,3-丁二烯聚合表现出很高的催化活性。生产的聚合物具有高顺 1,4 立体规整度（高达
• <i>C</i> ₂-Symmetric atropisomeric N-heterocyclic carbene–palladium(<scp>ii</scp>) complexes: synthesis, chiral resolution, and application in the enantioselective α-arylation of amides
  作者：Lingyu Kong、Yajie Chou、Muriel Albalat、Marion Jean、Nicolas Vanthuyne、Stéphane Humbel、Paola Nava、Hervé Clavier

  DOI：10.1039/d3dt01182h

  日期：——

  The concept of atropisomeric N-heterocyclic carbene (NHC)–metal complexes was extended to NHCs possessing a C2-symmetry and implemented to prepare palladium-based complexes. An in-depth study of the NHC precursors and the screening of various NHC ligands enabled us to circumvent the issue associated with the formation of meso complexes. A set of 8 atropisomeric NHC–palladium complexes were prepared

  阻转异构N-杂环卡宾(NHC)-金属配合物的概念被扩展到具有C 2对称性的NHC，并用于制备钯基配合物。对 NHC 前体的深入研究和各种 NHC 配体的筛选使我们能够规避与内消旋复合物形成相关的问题。制备了一组 8 种阻转异构体 NHC-钯配合物，并通过手性 HPLC 在制备规模上进行有效拆分，获得了高对映体纯度。这些配合物在酰胺的分子内 α-芳基化中表现出良好的活性，并且以优异的对映选择性（高达 98% ee）分离出各种环状产物。