1,3-bis[(N-phenyl)imino]-2-bromobenzene | 937205-24-8

• 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: 1,3-bis[(N-phenyl)imino]-2-bromobenzene
• 英文别名: bis(N-phenyl)-2-bromoisophthalaldimine；2,6-(PhN=CH)2C6H3-1-Br；1-[2-bromo-3-(phenyliminomethyl)phenyl]-N-phenylmethanimine
• CAS: 937205-24-8
• 化学式: C₂₀H₁₅BrN₂
• 分子量: 363.256
• InChiKey: NVNDYKJVVKBNIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,3-bis[(N-phenyl)imino]-2-bromobenzene 在 正丁基锂 、 potassium graphite 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 生成 C₂₀H₁₅N₂Sb
  参考文献：
  名称：

  （N），C，N-螯合锑（III）化合物还原的不同产物：单体丁二烯与1H-2,1-苯并氮杂苯并噻吩的竞争形成

  摘要：

  N，C，N螯合氯化锑（C 6 H 3 -2,6-（CH = NR）2 ] SbCl 2（R = Ph（1），t Bu（2），Dip（3）;浸= 2,6-我镨2 ç 6 ħ 3）与KC适量8或Li [的AlH 4 ]导致的单体stibinidenes的罕见例子的形成[C 6 H ^ 3 -2,6- （CH = NR）2 ] Sb（R = Ph（4），t Bu（5），Dip（6））。类似地，将化合物1或2还原为两个当量的K [B（s Bu）3 H]会导致生成二苯乙烯类化合物4和5。与此相反，化合物的类似反应3导致[C形成了前所未有的stibinidene 6 ħ 3 -2-（CH = NR）-6-（CH 2 NHR）]的Sb（7）（R =浸），在来自K [B（s Bu）3 H]的氢原子被结合到配体主链中。为了进一步了解与K [B（s Bu）3H]并评估取代对锑原子和侧基取代基的影响，我们制备了化合物[C

  DOI：

  10.1002/chem.201604142
• 作为产物：
  描述：

  1,3-双(二溴甲基)-2-溴苯 在 silver nitrate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1,3-bis[(N-phenyl)imino]-2-bromobenzene
  参考文献：
  名称：

  钯催化吲哚的直接C-2芳基化

  摘要：

  报道了含NCN Pincer配体的钯配合物的合成和催化评估。夹心钯配合物作为（预）催化剂对N取代的吲哚的CH芳基化反应显示出有效的催化活性，从而以中等至良好的收率和优异的区域选择性合成了2-芳基吲哚。

  DOI：

  10.1016/j.jorganchem.2014.02.017

文献信息

• Scandium and gadolinium complexes with aryldiimine NCN pincer ligands: Synthesis, characterization, and catalysis on isoprene and 1,5-hexadiene polymerization
  作者：Teng Jia、Shu-yun Xu、Li-cheng Huang、Wei Gao

  DOI：10.1016/j.poly.2018.02.010

  日期：2018.5

  analysis and the solid structures of 1c, 1d, 1f, and 2b were confirmed by X-ray diffraction analysis to be monomeric with N,C,N-tridentate ligands coordinating to the metal center in a typical meridional manner. In the presence of alkylaluminium and trityl borate, these well-defined complexes showed moderate to high activities in isoprene polymerization affording cis-1,4 enriched polymers (up to 98.3%). Moreover

  摘要带有三齿芳基二亚胺NCN钳形配体Ar [NCNH] ScCl2（THF）2（Ar = Ph（1a）; Ar = 2,6-Me2C6H3（1b），Ar = 2,6-Et2C6H3（1c）的几种scan和ado配合物，Ar = 2,6-iPr2C6H3（1d），Ar = p-MeC6H4（1e），Ar = 2,4,6-Me3C6H2（1f）），Ar [NCNMe] MCl2（THF）2（M = Sc，Ar ＝ 2，6-Me 2 C 6 H 3（2b）； M ＝ Gd，Ar ＝ 2，6-Me 2 C 6 H 3（3b），Ar ＝ 2，6-iPr 2 C 6 H 3（3d）），并通过锂合成iPrPh [NCNMe] ScCl 2（2d）。用nBuLi制备相应的配体，然后分别加入ScCl 3（THF）3或GdCl 3（THF）3。这些配合物通过元素分析得到了很好的表征，X射线衍射分析证实了1c，
• Synthesis of Bis(imino)aryl Iridium Pincer Complexes and Demonstration of Catalytic Hydrogen-Transfer Activity
  作者：Sarah H. Oakley、Michael P. Coogan、Richard J. Arthur

  DOI：10.1021/om070059f

  日期：2007.4.1

  Monomeric iridium(III) dihalide complexes containing terdentate bis(imino)aryl ligands, synthesized through oxidative addition of 2-bromoisophthalaldimines RNC(Br)NR (R = Ph 1, Mes 2, i-Pr 3, Me 4) to [IrCl(cod)]2 in the presence of NaBr to form [(RNCNR)IrBr2·solvent] (R = Ph 5, Mes 6, i-Pr 7, Me 8; solvent = MeCN; R = i-Pr 7a; DMSO), are reported. The development of a synthetic route to the complexes

  含二齿亚氨基双（亚氨基）芳基配体的二铱铱（III）卤化物配合物，是通过将2-溴间苯二甲酰胺RNC（Br）NR（R = Ph 1，Mes 2，i- Pr 3，Me 4）氧化成[IrCl（ cod）] 2在NaBr存在下形成[（RNCNR）IrBr 2 ·溶剂]（R = Ph 5，Mes 6，i -Pr 7，Me 8 ;溶剂= MeCN; R = i- Pr 7a; DMSO）。概述了开发复合物的合成路线，并讨论了该系列中每个成员的全部特征。3和4的X射线结构在与金属中心配位后确认亚氨基的保留。对[（PhNCNPh）IrBr 2 ·MeCN]（5）作为氢转移剂的催化活性的研究是通过在室温下酮（1,3-二苯丙酮和苯乙酮）经碱催化转移加氢成醇而进行的。承担。初步结果表明产生了催化物质，导致在室温下发生合理的转化。
• Substituent effect of diimino-palladium (II) pincer complexes on the catalysis of Sonogashira coupling reaction
  作者：Jin-Hua Zhang、Ping Li、Wen-Ping Hu、Hong-Xing Wang

  DOI：10.1016/j.poly.2015.04.031

  日期：2015.8

  Three NCN diimine ligands 4-6 were synthesized after condensation of isophthalaldehydes 1-3 and ani-lines. Treatment of 4-6 with Pd-2(dba)(3) in toluene resulted in the corresponding Pd-II-NCN-Bu-t (7), Pd-II-NCN-H (8) and Pd-II-NCN-NO2 (9) pincer complexes, respectively with high yields. Palladium pincers 7-9 and their precursors 4-6 were fully characterized by elemental analysis, IR, H-1 NMR and C-13 NMR spectroscopy. The molecular structures of 7b and 9b were also determined by X-ray single crystal diffraction. Sonogashira coupling of phenyl acetylene and 3-nitrobenzene catalyzed by 7-9 show that 9 exhibits the highest catalytic activity, suggesting that the electron withdrawing groups at the position-4 of palladium atom in palladium pincers will enhance their catalytic activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Bis(imino)aryl NCN Pincer Aluminum and Zinc Complexes: Synthesis, Characterization, and Catalysis on <scp>l</scp>-Lactide Polymerization
  作者：Zhizhou Liu、Wei Gao、Jingshun Zhang、Dongmei Cui、Qiaolin Wu、Ying Mu

  DOI：10.1021/om100344p

  日期：2010.11.22

  Reactions of 2,6-(ArN=CH)(2)C6H3Li with AlEt2Cl afford a number of NCN pincer aluminum complexes (2,6-(ArN=CH)(2)C6H3)AlEt2 (Ar = Ph (1), 2,6-Me2C6H3 (2), 2,6-Et2C6H3 (3), 2,6-(Pr2C6H3)-Pr-i (4)). Similar reactions of 2,6-(ArN=CH)(2)C6H3Li with ZnEtCl produce bisligated zinc complexes (2,6-(ArN=CH)(2)C6H3)(2)Zn (Ar = ph (5), 2,6-Me2C6H3 (6), 2,6-Et2C6H3 (7)) and monoligated NCN pincer zinc complex (2,6-(ArN=CH)(2)C6H3)ZnEt (Ar = 2,6-(Pr2C6H3)-Pr-i (8)). All complexes were characterized by H-1 and C-13 NMR spectroscopy, and the molecular structures of complexes 3, 4, 6, 7, and 8 were determined by X-ray crystallography. The X-ray diffraction analysis reveals that both complexes 3 and 4 adopt a distorted trigonal-bipyramidal geometry around the aluminum central metal with three carbon atoms in the equator and the two imine nitrogen atoms in the apical positions. Complexes 6 and 7 adopt a distorted tetrahedral geometry around their zinc metal centers, while complex 8 adopts a square-planar geometry around its metal center. All these Al and Zn complexes are efficient initiators for L-lactide ring-opening polymerization in the presence of benzyl alcohol, and the polymerization reaction takes place in an immortal manner. The productivity of the Zn complexes is generally higher than that of the Al complexes under similar conditions.