1,3-双(苯并咪唑-2-基)-2-甲基丙烷 | 84258-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1,3-双(苯并咪唑-2-基)-2-甲基丙烷
• 英文名称: 1,3-bis-(benzimidazolyl)-2-methylpropane
• 英文别名: 1,3-bis(benzimidazol-2-yl)-2-methylpropane；1,1-bis(1H-benzimidazol-2-ylmethyl)ethane；bis(2-benzimidazolyl)-3-butane；2-[3-(1H-benzimidazol-2-yl)-2-methylpropyl]-1H-benzimidazole
• CAS: 84258-51-5
• 化学式: C₁₈H₁₈N₄
• 分子量: 290.368
• InChiKey: IBWUQGUKVQLDPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trichlorotris(tetrahydrofuran)chromium(III) 、 1,3-双(苯并咪唑-2-基)-2-甲基丙烷 以 四氢呋喃 为溶剂， 反应 12.0h， 以92%的产率得到1,1-bis(1H-benzimidazol-2-ylmethyl)ethane chromium(III) chloride
  参考文献：
  名称：

  Alternating α-Olefin Distributions via Single and Double Insertions in Chromium-Catalyzed Ethylene Oligomerization

  摘要：

  The catalytic oligomerization of ethylene with chromium-based complexes containing bis(benzimidazolemethyl)amine (BIMA) ligands results in alternating distributions of linear alpha-olefins (LAOs). Extremely high activities are obtained (>100 000 g mmol(-1) h(-1) bar(-1)) with N-alkyl-substituted BIMA ligands, whereas bulky groups on the central nitrogen or alternative central donors result in much lower activities. Variations in the ligand backbone, as well as methylation of the benzimidazole units, lead to reduction in activity. The alternating LAO distributions have been mathematically analyzed using second -order recurrence relations. The shape of the distributions is affected by ethylene pressure (1-4 bar) and by the cocatalyst to some degree. On the basis of the results and analysis presented herein, we propose that the alternating behavior originates from the ability of these chromium BIMA catalysts to undergo single as well as double ethylene insertion reactions. A minor second distribution (<5 wt %) of 2-ethyl-1-alkenes is obtained under certain conditions, resulting from incorporation of 1-butene. DFT studies (MO6L) and experimental observations regarding the reaction between AIMe(3) and the N-methyl BIMA ligand 2 have shown that deprotonation of the benzimidazole N-H units can occur, which suggests a change in coordination of the BIMA ligand under oligomerization conditions.

  DOI：

  10.1021/acs.organomet.6b00671
• 作为产物：
  描述：

  3-甲基戊二酸酐 、 邻苯二胺 以 xylene 为溶剂， 反应 2.0h， 以37%的产率得到N,N'-bis-(4-carboxy-3-methylbutyryl)-o-phenylenediamine
  参考文献：
  名称：

  Lombardino, Joseph G.; Ewing, Frank E., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 923 - 924

  摘要：

  DOI：

文献信息

• The effect of the central donor in bis(benzimidazole)-based cobalt catalysts for the selective cis-1,4-polymerisation of butadiene
  作者：Renan Cariou、Juan J. Chirinos、Vernon C. Gibson、Grant Jacobsen、Atanas K. Tomov、George J. P. Britovsek、Andrew J. P. White

  DOI：10.1039/c0dt00402b

  日期：——

  of bis(benzimidazole)-based cobalt(II) dichloride complexes containing a range of different central donors has been synthesized and characterized. The nature of the central donor affects the binding of the ligand to the cobalt centre and determines the coordination geometry of the metal complexes. All complexes have been shown to catalyse the polymerization of butadiene, in combination with MAO as

  一系列 双（苯并咪唑）-基于 二氯化钴已经合成并表征了包含一系列不同中央供体的复合物。中心给体的性质影响配体与钴中心的结合并确定金属配合物的配位几何形状。已证明所有配合物都可与丁二烯一起催化丁二烯的聚合。毛 作为助催化剂， 顺式-1,4-聚丁二烯具有高选择性。中心给体的性质对催化剂的聚合活性有显着影响，但不影响聚合物的微观结构。的加法PPh 3 通常会提高这些聚合物的聚合活性 钴 催化剂和结果主要（60–70％） 1,2-乙烯基-聚丁二烯。
• X-ray crystal structures, spectroscopic and magnetic measurements of dinuclear alkoxo-bridged copper(II) compounds with substituted bis(2-benzimidazolyl)alkane ligands. First X-ray structure of a copper(II) dinuclear propoxo-bridged compound
  作者：Gerard A van Albada、Ilpo Mutikainen、Ivonne Riggio、Urho Turpeinen、Jan Reedijk

  DOI：10.1016/s0277-5387(01)00903-2

  日期：2002.1

  new alkoxo-bridged dinuclear copper(II) compounds are described, all having the general formula [Cu2(L)2(RO−)2](ClO4)2(ROH)y(H2O)z, in which L=b2b (bis(2-benzimidazolyl)-2-butane) and b3b (bis(2-benzimidazolyl)-3-butane), ROH=MeOH, EtOH, 1-PrOH, y=1 or 2, z=0 or 3. The X-ray structure has been solved from two compounds; [Cu2(b2b)2(OCH3)2](ClO4)2(CH3OH)2(H2O)3 (1) and from compound [Cu2(b3b)2(C3H7O)2](ClO4)2(C3H7OH)2

  的合成和三个新的烷氧桥连的双核铜表征被描述（II）化合物中，所有具有通式[铜2（L）2（RO - ）2 ]（CLO 4）2（ROH）ý（H 2 ö ）z，其中L = b2b（双（2-苯并咪唑基）-2-丁烷）和b3b（双（2-苯并咪唑基）-3-丁烷），ROH = MeOH，EtOH，1-PrOH，y = 1或2 ，z = 0或3。X射线结构已由两种化合物解析；[Cu 2（b2b）2（OCH 3）2 ]（ClO 4）2（CH3 OH）2（H 2 O）3（1）和化合物[Cu 2（b3b）2（C 3 H 7 O）2 ]（ClO 4）2（C 3 H 7 OH）2（3）。这两种化合物由双核Cu（II）单元和1个桥联的甲氧基和一个3个桥联的丙氧基组成，两个配体通过N与每个铜相连，从而提供了方形的CuN 2 O 2发色团。后者是第一个带有架桥丙氧基的双核Cu（II）X射线结构。两种双核化合物都是抗磁性的。
• A dinuclear end-on azide-bridged copper(II) compound with weak antiferromagnetic interaction – Synthesis, characterization, magnetism and X-ray structure of bis[(μ-azido-κN1)-(azido-κN1)(1,3-bis(benzimidazol-2-yl)-2-methylpropane)copper(II)]
  作者：Gerard A. van Albada、Ilpo Mutikainen、Olivier Roubeau、Jan Reedijk

  DOI：10.1016/j.molstruc.2012.11.033

  日期：2013.3

  [Cu(μ-N3-κN1)(N3-κN1)(bbmp)]2 is reported. Synthesis, characterization, physical properties are determined in detail, together with its 3D structure. The dinuclear end-on azide-bridged copper(II) compound displays a weak antiferromagnetic interaction, despite the fact that the magnetic orbitals overlap. The Cu–Cu contact distance is 3.1867(8) A, while the Cu–Nazide–Cu angle is 103.41(14)°. The IR spectra of the azido

  摘要 报道了式[Cu(μ-N3-κN1)(N3-κN1)(bbmp)]2的中心对称双核化合物。详细确定合成、表征、物理特性及其 3D 结构。尽管磁轨道重叠，但双核末端叠氮化物桥连铜 (II) 化合物显示出弱的反铁磁相互作用。Cu-Cu 接触距离为 3.1867(8) A，而 Cu-Nazide-Cu 角为 103.41(14)°。叠氮配体的红外光谱与这种配位叠氮化物的预期一致。
• Alternating α-Olefin Distributions via Single and Double Insertions in Chromium-Catalyzed Ethylene Oligomerization
  作者：Atanas K. Tomov、James D. Nobbs、Juan J. Chirinos、Prabhjot K. Saini、Robert Malinowski、Sarah K. Y. Ho、Craig T. Young、David S. McGuinness、Andrew J. P. White、Mark R. J. Elsegood、George J. P. Britovsek

  DOI：10.1021/acs.organomet.6b00671

  日期：2017.2.13

  The catalytic oligomerization of ethylene with chromium-based complexes containing bis(benzimidazolemethyl)amine (BIMA) ligands results in alternating distributions of linear alpha-olefins (LAOs). Extremely high activities are obtained (>100 000 g mmol(-1) h(-1) bar(-1)) with N-alkyl-substituted BIMA ligands, whereas bulky groups on the central nitrogen or alternative central donors result in much lower activities. Variations in the ligand backbone, as well as methylation of the benzimidazole units, lead to reduction in activity. The alternating LAO distributions have been mathematically analyzed using second -order recurrence relations. The shape of the distributions is affected by ethylene pressure (1-4 bar) and by the cocatalyst to some degree. On the basis of the results and analysis presented herein, we propose that the alternating behavior originates from the ability of these chromium BIMA catalysts to undergo single as well as double ethylene insertion reactions. A minor second distribution (<5 wt %) of 2-ethyl-1-alkenes is obtained under certain conditions, resulting from incorporation of 1-butene. DFT studies (MO6L) and experimental observations regarding the reaction between AIMe(3) and the N-methyl BIMA ligand 2 have shown that deprotonation of the benzimidazole N-H units can occur, which suggests a change in coordination of the BIMA ligand under oligomerization conditions.
• Lombardino, Joseph G.; Ewing, Frank E., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 923 - 924
  作者：Lombardino, Joseph G.、Ewing, Frank E.

  DOI：——

  日期：——