1-(2,6-dimethylphenylimino)acenaphthylen-2-one | 913814-01-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2,6-dimethylphenylimino)acenaphthylen-2-one
• 英文别名: 2-[(2,6-xylyl)imino]acenaphthylen-1-one；((2,6-dimethylphenyl)imino)-acenaphthenone；(2E)-2-[(2,6-Dimethylphenyl)imino]acenaphthylen-1(2H)-one；2-(2,6-dimethylphenyl)iminoacenaphthylen-1-one
• CAS: 913814-01-4
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: RMECEOORFIMKPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  514.6±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 1-(2,6-dimethylphenylimino)acenaphthylen-2-one 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以79%的产率得到
  参考文献：
  名称：

  刚性N-（芳基）亚氨基-庚二酮（Ar-BIAO）的格氏反应中过渡态的建模：实验与计算相结合的研究

  摘要：

  我们提出了将格氏试剂RMgBr / RMgI（R = Me，Et）添加到各种空间刚性N-（芳基）亚氨基-en烯酮（Ar-BIAO）（Ar = 2,6- i Pr 2 C 6 H 3（1），2,6-Me 2 C 6 H 3（2）和2,4,6-Me 3 C 6 H 2（3）配体）。在实验方法中，当化合物1 - 3分别在室温下用RMgBr（R =甲基，乙基）处理，相应的外消旋Ñ-（芳基）亚氨基-en烯-1-醇（Ar-BIAOH）化合物（Ar = 2,6- i Pr 2 C 6 H 3，R = Me（1a），Et（1b）; Ar = 2,6-得到Me 2 C 6 H 3，R = Me（2a），Et（2b）；和Ar = 2,4,6-Me 3 C 6 H 2，R = Me（3a），Et（3b））在产率高达82％。通过光谱和燃烧分析对Ar-BIAOH化合物进行了表征。化合物1a – 3a的固态结构通过单

  DOI：

  10.1071/ch14399
• 作为产物：
  描述：

  2,6-二甲基苯胺 、 苊醌 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 1-(2,6-dimethylphenylimino)acenaphthylen-2-one
  参考文献：
  名称：

  取代芳基亚胺的合成和 X 射线晶体学表征

  摘要：

  摘要 我们报告了 α-二亚胺 1,4-双(2,5-二叔丁基苯基)-2,3-二甲基-1,4-二氮杂-1,3-丁二烯、1 和 α-亚氨基酮的合成2-[(3,5-xylyl)imino]acenaphthylen-1-one, 4, 和 2-[(4-chlorophenyl)imino]acenaphthylen-1-one, 5, 均已通过 1H NMR, 13C 表征NMR、IR 和 X 射线晶体学。此外，我们还报告了先前未知的 α-二亚胺 Ar-BIAN（Ar-BIAN = 双（芳基亚氨基）苊；Ar = 3,5-二甲苯基，2；Ar = 4-氯苯基，3）和 α -亚氨基酮 2-[(2,6-二甲苯基)亚氨基]acenaphthylen-1-one, 6. 在溶液中，4 和 5 显示了在 DMSO-d6 中用可变温度 1H NMR 观察到的流动行为，这归因于 E 和Z形式的亚胺。

  DOI：

  10.1016/j.molstruc.2011.02.027

文献信息

• Syntheses and solid state structures of zinc (II) complexes with Bi-dentate N-(Aryl)imino-acenapthenone (Ar-BIAO) ligands
  作者：SRINIVAS ANGA、SUPRIYA REJ、KISHOR NAKTODE、TIGMANSU PAL、TARUN K PANDA

  DOI：10.1007/s12039-014-0756-z

  日期：2015.1

  We have synthesized five zinc complexes of molecular formulae [ZnCl2(2,6-dimethylphenyl-BIAO)]2 (1a), [ZnBr2(2,6-dimethylphenyl-BIAO)]2 (1b), [ZnI2(2,6-dimethylphenyl-BIAO)]2(1c), [ZnBr2(mes-BIAO)]2(2b) and [ZnBr2(dipp-BIAO)] (3b) with rigid unsymmetrical iminoacenaphthenone ligands, (2,6-dimethylphenyl-BIAO) (1), (mesityl-BIAO) (2) and (2,6-diisopropylphenyl-BIAO) (3). The zinc complex 1a was prepared by the reaction of ZnCl2 and neutral (mesityl-BIAO) (1). However, complexes 1b, 2b and 3b were obtained by the treatment of ZnBr2 and neutral ligands 1–3 respectively in 1:1 molar ratio in dichloromethane at ambient temperature. In a similar reaction of ZnI2 with (2,6-dimethylphenyl-BIAO) (1) in dichloromethane the corresponding iodo-complex 1c was obtained in good yield. All the zinc (II) complexes are characterized by FT-IR, 1H and 13C1H} NMR spectroscopic techniques. The solid state structures of the complexes 1a, 1b, 1c, 2b and 3b are confirmed by single crystal X-ray diffraction analysis. The molecular structures of complexes 1a, 1b, 1c and 2b reveal the dimeric nature of the complexes and subsequently the centre atom zinc is penta-coordinated to adopt distorted trigonal bipyramidal geometry around it. In contrast, the complex 3b is in monomeric in nature due to bulkier size of the ligand and zinc ion is tetra coordinated to adopt distorted tetrahedral geometry.

  我们合成了五种锌配合物，其分子式分别为 [ZnCl2(2,6-二甲基苯基-BIAO)]2 (1a), [ZnBr2(2,6-二甲基苯基-BIAO)]2 (1b), [ZnI2(2,6-二甲基苯基-BIAO)]2(1c), [ZnBr2(mes-BIAO)]2(2b) 和 [ZnBr2(dipp-BIAO)] (3b)，这些配合物含有刚性的不对称亚胺基苊酮配体，分别是 (2,6-二甲基苯基-BIAO) (1), (2,6-二甲基苯基-BIAO) (2) 和 (2,6-二异丙基苯基-BIAO) (3)。锌配合物 1a 是通过 ZnCl2 与中性 (2,6-二甲基苯基-BIAO) (1) 反应制备的。然而，配合物 1b, 2b 和 3b 是通过 ZnBr2 分别与中性配体 1–3 在二氯甲烷中以 1:1 摩尔比在室温下反应得到的。在类似的反应中，ZnI2 与 (2,6-二甲基苯基-BIAO) (1) 在二氯甲烷中反应，得到了相应的碘配合物 1c，产率良好。所有的锌(II)配合物都通过 FT-IR、1H 和 13C1H} NMR 光谱技术进行了表征。配合物 1a, 1b, 1c, 2b 和 3b 的固态结构通过单晶 X 射线衍射分析得到确认。配合物 1a, 1b, 1c 和 2b 的分子结构揭示了这些配合物的二聚性质，随后中心原子锌采取扭曲的三角双锥几何结构。相比之下，由于配体和锌离子的体积较大，配合物 3b 是单体的，锌离子采取扭曲的四面体几何结构。
• Zinc catalyzed Guanylation reaction of Amines with Carbodiimides/ Isocyanate leading to Guanidines/Urea derivatives formation
  作者：JAYEETA BHATTACHARJEE、MITALI SACHDEVA、INDRANI BANERJEE、TARUN K PANDA

  DOI：10.1007/s12039-016-1096-y

  日期：2016.6

  donating groups underwent higher conversion than the amines having electron withdrawing groups to afford corresponding guanidine or urea derivatives. A possible mechanism involving penta-coordinated zinc transition state for the catalytic reaction is presented. We report the highly chemo-selective catalytic addition of N–H bonds from various aromatic amines to carbodiimides and isocyanates using (Ar-BIAO)ZnCl2

  我们报道了使用（Ar-BIAO）ZnCl 2络合物[Ar-BIAO = N-（芳基）亚氨基-en烯酮，Ar = 2,6]，从各种芳香胺向碳二亚胺和异氰酸酯的N–H键的高化学选择性催化加成反应-Me 2 C 6 H 3（1），2,4,6 Me 3 C 6 H 2（2），2,6- i Pr 2 C 6 H 3（3）]作为制备胍的前催化剂和尿素衍生物的产率为55-90％。配合物3显示出比类似配合物1高的催化活性和2在相似的反应条件下。N-H键与杂聚枯烯的催化鸟嘌呤化作用显示出广阔的底物范围。具有给电子基团的胺比具有吸电子基团的胺具有更高的转化率，以提供相应的胍或脲衍生物。提出了涉及五配位锌过渡态的催化反应的可能机理。 我们报道了使用（Ar-BIAO）ZnCl 2络合物[Ar-BIAO = N-（2,6-二异丙基苯基）亚氨基-en烯酮，从各种芳族胺到碳二亚胺和异氰酸酯的N-H键的高化学选择性催化加成[
• Chromium Complexes with Acenaphthene Imine Derivative Ligands Synthesis and Catalysis on Diene Polymerization
  作者：Bo Gao、Wei Gao、Qiaolin Wu、Xuyang Luo、Jingshun Zhang、Qing Su、Ying Mu

  DOI：10.1021/om200733e

  日期：2011.10.24

  Treatment of the bis(arylimino)acenaphthene (BIAN) ligands with CrCl2(THF)(2) in THF affords mononuclear complexes of (Ar)BIANCrCl(2)(THF)(2) (3a, Ar = 2-(PrC6H4)-Pr-i; 3b, Ar = 2,6-Me2C6H3) and chlorine-bridging dinudear complexes (Ar)BIANCrCl(mu-Cl)(3)Cr(THF)(Ar)BIAN (3c, Ar = 2,6-Et2C6H3; 3d, Ar = 2,6-(Pr2C6H3)-Pr-i). The molecular structures of 3b-3d were characterized by X-ray diffraction analysis, and all the chromium atoms are in octahedral geometries. Similar reactions of N-(arylimino)acenaphthenones with CrCl2(THF)(2) afford the dinudear chromium complexes with 1,1'-bis(2-aryliminoacenaphthene-1-olate) tetradentate ligands ArBIAOCr(2)Cl(4)(THF)(2) (4b, Ar = 2,6-Me2C6H3; 4c, Ar = 2,6-Et2C6H3) via a pinacol cross-coupling reaction. Upon activation with MAO, these complexes show moderate-to-high activities in butadiene and isoprene polymerization, affording a cis-1,4-enriched polymer.
• Oligomerization of Ethylene Using New Tridentate Iron Catalysts Bearing α-Diimine Ligands with Pendant S and P Donors
  作者：Brooke L. Small、Ray Rios、Eric R. Fernandez、Deidra L. Gerlach、Jason A. Halfen、Michael J. Carney

  DOI：10.1021/om1007743

  日期：2010.12.27

  Stoichiometric Schiff base condensations of sterically bulky primary amines with acenaphthene quinone yield isolable monoimines In the presence of iron(II) chloride the remaining ketone reacts with a second primary amine bearing a pendant donor atom to give asymmetric tridentate a diimine complexes that possess remarkable structural variability A series of NNP and NNS tridentate iron(II) complexes are prepared these coordination compounds become active catalysts for ethylene oligomerization when activated with methylalumoxanes X ray crystallographic studies of the precatalyst complexes confirm that the ligand binds in a tridentate fashion Correlations between the precatalyst solid state structures and catalyst activity and a olefin product distribution are explored
• Tailoring Polyethylenes by Nickel Complexes Bearing Modified 1-(2-Benzhydrylnaphthylimino)-2-phenyliminoacenaphthylene Derivatives
  作者：Chunyan Wen、Shifang Yuan、Qisong Shi、Erlin Yue、Diansheng Liu、Wen-Hua Sun

  DOI：10.1021/om5010226

  日期：2014.12.22

  A series of 1-(2-benzhydrylnaphthylimino)-2-phenyliminoacenaphthylene derivatives (L1-L5) was synthesized, characterized, and then reacted with (DME)NiBr2 to form the corresponding [1-(2-benzhydrylnaphthylimino)-2-phenyliminoacenaphthyl]nickel bromides (C1-C5). All nickel complexes were fully characterized by their FT-IR spectra and elemental analysis. The molecular structures of the representative complexes C1 and C4 were also determined by single-crystal X-ray diffraction. On activation with either methylaluminoxane (MAO) or diethylaluminum chloride (Et2AlCl), all title nickel complexes showed high activities toward ethylene polymerization; the resulting polyethylenes showed molecular weights higher than those obtained by using the nickel analogues bearing (2-benzhydrylnaphthylimino)pyridines and also had branches lower than those obtained by using other diiminoacenaphthylnickel analogues. Therefore, the modification of ligands could affect the catalytic behavior of their nickel complexes in order to tailor the molecular weights and branches of the resulting polyethylenes.