N,N-bis((1H-benzimidazol-2-yl)methyl)-N-(cyclohexyl)amine | 894369-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N,N-bis((1H-benzimidazol-2-yl)methyl)-N-(cyclohexyl)amine
• 英文别名: N,N-bis(1H-benzimidazol-2-ylmethyl)cyclohexanamine
• CAS: 894369-66-5
• 化学式: C₂₂H₂₅N₅
• 分子量: 359.474
• InChiKey: GEPSKIQWDTXIIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trichlorotris(tetrahydrofuran)chromium(III) 、 N,N-bis((1H-benzimidazol-2-yl)methyl)-N-(cyclohexyl)amine 以 四氢呋喃 为溶剂， 反应 12.0h， 以74%的产率得到N,N-bis((1H-benzimidazol-2-yl)methyl)-N-(cyclohexyl)amine 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：

  diethyl 2,2'-(cyclohexylimino)diacetate 、 邻苯二胺 以74%的产率得到N,N-bis((1H-benzimidazol-2-yl)methyl)-N-(cyclohexyl)amine
  参考文献：
  名称：

  中心供体在双（苯并咪唑）基钴催化剂中对丁二烯选择性顺式-1,4-聚合的作用†

  摘要：

  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。

  DOI：

  10.1039/c0dt00402b

文献信息

• Diene Polymerisation
  申请人：Jacobsen Grant Berent

  公开号：US20100022724A1

  公开（公告）日：2010-01-28

  A process for producing homopolymers or copolymers of conjugated dienes comprising contacting monomeric material comprising at least one conjugated diene with a catalyst system comprising two or more different transition metal compounds and optionally one or more activators. Preferred transition metal compounds are based on cobalt and chromium, especially complexes thereof having benzimidazole ligands.

  生产共轭二烯的同聚物或共聚物的过程，包括将至少含有一种共轭二烯的单体材料与催化剂体系接触，所述催化剂体系包括两种或更多不同的过渡金属化合物和可选的一个或多个活化剂。首选的过渡金属化合物基于钴和铬，特别是具有苯并咪唑配体的配合物。
• US8124698B2
  申请人：——

  公开号：US8124698B2

  公开（公告）日：2012-02-28
• 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.
• 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。