N,N'-Di-<2-methylenbenzimidazol>-aethylendiamin | 145533-47-7

• 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'-Di-<2-methylenbenzimidazol>-aethylendiamin
• 英文别名: N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine；N,N'-bis-(1H-benzoimidazol-2-ylmethyl)-ethane-1,2-diamine；N,N'-bis(1H-benzimidazol-2-ylmethyl)ethane-1,2-diamine
• CAS: 145533-47-7
• 化学式: C₁₈H₂₀N₆
• 分子量: 320.397
• InChiKey: ZOSWODIVQNQUAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.4
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 N,N'-Di-<2-methylenbenzimidazol>-aethylendiamin 以 甲醇 为溶剂， 生成 Cu(N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine)(ClO4)2
  参考文献：
  名称：

  Structure, spectra and redox behaviour of copper(II) complexes of bis(benzimidazolyl)diamine ligands

  摘要：

  The linear quadridentate ligand N,N'-bis(benzimidazol-2-ylethyl)ethane-1,2-diamine (L1) and its 1-methylbenzimidazole analogue (L2) and homologues form 1:1 complexes with Cu (ClO4)2; L1 also forms complexes of the types CuL1X2 where X = NO3, PF6, Br or Cl and CuL1(X)Y where X = Cl or Br and Y = ClO4 or Br. Deep blue CuL1Br2.2H2O crystallizes in the monoclinic space group C2/c with Z = 4, a = 9.919(2), b = 16.626(3), c = 14.102(3) angstrom and beta = 94.39(2)-degrees. The structure was solved by Patterson and Fourier difference methods and refined by the least-squares technique to R = 0.064 for 2195 independent reflections with / > 1.5sigma(/). The molecule lies on a two-fold axis symmetrically around Cu(II). The co-ordination around Cu(II) is found to be square planar with two amino nitrogens and two benzimidazole nitrogens forming the equatorial plane [Cu-N 1.983(3) and 2.037(4) angstrom]. The bromides are at longer distances [3.349(1) angstrom] in axial sites. Ligand field and EPR spectra indicate that one bromide or chloride ion is axially co-ordinated to Cu(II) in [CuL1]2+. This ion exhibits quasi-reversible redox behaviour. Electrochemical studies of the dihalides in methanol have established the presence of [CuL1X2], [CuL1(X)]+ and [CuL1]2+ in equilibrium. In complexes with 565 [CuL4]2+ [L4 = N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine] and 555 [CuL3]2+ [L3 = N,N'-bis(1-methylbenzimidazol-2-ylmethyl)propane-1,3-diamine] chelate rings, Cu(II) does not seem to lie in the N4 square plane, as revealed by their low A(parallel-to) values and irreversible electrochemical behaviour. The Cu(II)-Cu(I) redox potentials in methanol are in the order [CuL1]2+ < [CuL3]2+ < [CuL4]2+; this illustrates that six-membered chelate rings are suitable to stabilize Cu(II), when Cu-N sigma interactions are favourable.

  DOI：

  10.1039/dt9920003377
• 作为产物：
  描述：

  乙二胺 、 2-chloromethyl-1H-benzimidazole hydrochloride 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N,N'-Di-<2-methylenbenzimidazol>-aethylendiamin
  参考文献：
  名称：

  Structure, spectra and redox behaviour of copper(II) complexes of bis(benzimidazolyl)diamine ligands

  摘要：

  The linear quadridentate ligand N,N'-bis(benzimidazol-2-ylethyl)ethane-1,2-diamine (L1) and its 1-methylbenzimidazole analogue (L2) and homologues form 1:1 complexes with Cu (ClO4)2; L1 also forms complexes of the types CuL1X2 where X = NO3, PF6, Br or Cl and CuL1(X)Y where X = Cl or Br and Y = ClO4 or Br. Deep blue CuL1Br2.2H2O crystallizes in the monoclinic space group C2/c with Z = 4, a = 9.919(2), b = 16.626(3), c = 14.102(3) angstrom and beta = 94.39(2)-degrees. The structure was solved by Patterson and Fourier difference methods and refined by the least-squares technique to R = 0.064 for 2195 independent reflections with / > 1.5sigma(/). The molecule lies on a two-fold axis symmetrically around Cu(II). The co-ordination around Cu(II) is found to be square planar with two amino nitrogens and two benzimidazole nitrogens forming the equatorial plane [Cu-N 1.983(3) and 2.037(4) angstrom]. The bromides are at longer distances [3.349(1) angstrom] in axial sites. Ligand field and EPR spectra indicate that one bromide or chloride ion is axially co-ordinated to Cu(II) in [CuL1]2+. This ion exhibits quasi-reversible redox behaviour. Electrochemical studies of the dihalides in methanol have established the presence of [CuL1X2], [CuL1(X)]+ and [CuL1]2+ in equilibrium. In complexes with 565 [CuL4]2+ [L4 = N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine] and 555 [CuL3]2+ [L3 = N,N'-bis(1-methylbenzimidazol-2-ylmethyl)propane-1,3-diamine] chelate rings, Cu(II) does not seem to lie in the N4 square plane, as revealed by their low A(parallel-to) values and irreversible electrochemical behaviour. The Cu(II)-Cu(I) redox potentials in methanol are in the order [CuL1]2+ < [CuL3]2+ < [CuL4]2+; this illustrates that six-membered chelate rings are suitable to stabilize Cu(II), when Cu-N sigma interactions are favourable.

  DOI：

  10.1039/dt9920003377

文献信息

• Method for Producing Aromatic Compound Polymer
  申请人：Higashimura Hideyuki

  公开号：US20090018309A1

  公开（公告）日：2009-01-15

  A method for producing an aromatic compound polymer comprising oxidatively polymerizing one or more of aromatic compound(s) having two or more hydrogen atoms directly connected to aromatic ring(s), in the presence of an oxidizing agent, wherein the method employs a catalyst composed of a transition metal complex or a catalyst prepared from a transition metal complex and an activating agent, and said catalyst has a parameter P defined by the following formula (A) of 0.50 or more, and a parameter Eo defined by the following formula (B) of 0.50 [V] or more: P=Af/Ai (A) and Eo =( Epa+Epc )/2[V]  (B).

  一种生产芳香族化合物聚合物的方法，包括在氧化剂存在下氧化聚合具有两个或更多氢原子直接连接到芳香环的一个或多个芳香族化合物，其中该方法采用由过渡金属配合物或由过渡金属配合物和活化剂制备的催化剂，所述催化剂具有以下公式（A）定义的参数P，P的值为0.50或更高，并且具有以下公式（B）定义的参数Eo，Eo的值为0.50 [V]或更高：P=Af/Ai（A）和Eo=(Epa+Epc)/2[V]（B）。
• RESIN COMPOSITION AND PROCESS FOR PRODUCING THE SAME
  申请人：Japan as represented by Secretary of Agency of Industrial Science and Technology

  公开号：EP1114836A1

  公开（公告）日：2001-07-11

  A curable resin composition, which comprises a resin formed, in the presence of a transition metal complex, by polymerizing an oxidative-polymerizable compound that contains a phenol-compound-containing vegetable oil. A method for producing a curable resin composition comprising a resin formed, in the presence of a catalyst, by polymerizing an oxidative-polymerizable compound that contains a phenol-compound-containing vegetable oil, wherein the catalyst is a transition metal complex. The curable resin composition is useful as a raw material for a urushi-like coating, a friction material, a brake lining material, a brake pad material, a material for forming a coating film, a compound for a recording material, a raw material for an ink, a raw material for a coating, a raw material for a adhesive, a raw material for an epoxy resin, a raw material for a photoresist or antioxidant, and a starting material for a functional polymer.

  一种可固化树脂组合物，它包括在过渡金属络合物存在下，通过聚合含有含酚化合物的植物油的可氧化聚合化合物而形成的树脂。一种生产可固化树脂组合物的方法，该树脂组合物包括在催化剂存在下，通过聚合含有含酚化合物植物油的可氧化聚合化合物而形成的树脂，其中催化剂为过渡金属络合物。这种可固化树脂组合物可用作乌拉石般的涂层的原料、摩擦材料、制动衬片材料、制动片材料、形成涂膜的材料、记录材料的化合物、油墨的原料、涂层的原料、粘合剂的原料、环氧树脂的原料、光刻胶或抗氧化剂的原料以及功能聚合物的起始原料。
• METHOD FOR PRODUCING AROMATIC COMPOUND POLYMER
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1767560A1

  公开（公告）日：2007-03-28

  A method for producing an aromatic compound polymer comprising oxidatively polymerizing one or more of aromatic compound(s) having two or more hydrogen atoms directly connected to aromatic ring(s), in the presence of an oxidizing agent, wherein the method employs a catalyst composed of a transition metal complex or a catalyst prepared from a transition metal complex and an activating agent, and said catalyst has a parameter P defined by the following formula (A) of 0.50 or more, and a parameter Eo defined by the following formula (B) of 0.50 [V] or more: P=Af/Ai (wherein Ai represents an absorbance at an absorption maximum belonging in an absorption band located at the longest wavelength side in an absorption spectrum obtained for a solution containing the catalyst, in a ultraviolet to near-infrared wavelength region from 200 nm to 800 nm, and Af represents an absorbance at the same wavelength applied to the Ai, in an absorption spectrum in the above wavelength region obtained for a solution prepared by adding 3 equivalent of water per mole of the metal contained in the catalyst to the solution), and Eo=Epa+Epc/2V (wherein, Epa represents a peak potential at the oxidation side of an oxidation-reduction potential derived from the transition metal contained in the catalyst, at a potential of 0.50 [V] or more based on oxidation-reduction potential of ferrocene/ferrocenium ion measured with a cyclic voltammetry for the solution containing the catalyst, and Epc represents a peak potential at the reduction side corresponding to Epa by the same measurement).

  一种生产芳香族化合物聚合物的方法，包括在氧化剂存在下，氧化聚合一种或多种具有两个或两个以上氢原子直接连接到芳香环上的芳香族化合物，其中该方法采用由过渡金属络合物组成的催化剂或由过渡金属络合物和活化剂制备的催化剂，所述催化剂的参数P由下式(A)定义为0.50或以上，参数Eo由下式(B)定义为0.50[V]或以上：P=Af/Ai (其中，Ai 表示在含有催化剂的溶液的吸收光谱中，在 200 纳米至 800 纳米的紫外至近红外波长区域内，属于最长波长侧的吸收带的吸收最大值处的吸光度；Af 表示在通过向溶液中加入每摩尔催化剂所含金属 3 当量的水而制备的溶液的吸收光谱中，在上述波长区域内，与 Ai 相同波长处的吸光度），以及 Eo=Epa+Epc/2V (其中，Epa 代表由催化剂所含过渡金属衍生的氧化还原电位的氧化侧峰值电位，电位值为 0.50 [V] 或更高，该电位值基于对含有催化剂的溶液用循环伏安法测得的二茂铁/二茂铁离子的氧化还原电位；Epc 代表与 Epa 相对应的还原侧峰值电位，该测量值与 Epa 相同）。
• Method for producing aromatic compound polymer
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2241547A1

  公开（公告）日：2010-10-20

  A method for producing an aromatic compound polymer by oxidatively polymerizing an aromatic compound in the presence of an oxidizing agent, wherein the method employs (a) a catalyst composed of a transition metal complex or (b) a catalyst prepared from a transition metal complex and an activating agent, and said transition metal complex is a vanadium di-nuclear complex represented by the following general formula (1-3): wherein A1, A2, A3 and A4 each independently represent an oxygen atom, or NR11, and B1, B2, B3 and B4 each independently represent -O- or NR12-; R1, R2, R3, R4, R5, R6, R7 and R8 each independently represent a C1-30 hydrocarbon group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; or a C1-40 hydrocarbonoxy group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; R9 and R10 each independently represent a C1-20 alkylene group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; or R9 and R10 represent a C6-60 arylene group optionally substituted by a C1-50 alkyl, C7-50 aralkyl, C1-50 alkoxy, nitro, cyano or halogen group; or R9 and R10 represent -O-, -S--SO2- or NR13-; and when R9 and R10 exist in a plural number respectively, they may be the same or different; m and n each independently represent an integer of 1 to 7; R11, R12 and R13 each independently represent a hydrogen atom or a C1-30 hydrocarbon group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; when R11, R12 and R13 exist in a plural number respectively, they may be the same or different; when both of A1 and A2 and/or both of A3 and A4 are together NR11 respectively, two R11s may combine to form a C1-20 divalent hydrocarbon group optionally substituted by a C1-30 hydrocarbon, C1-40 hydrocarbonxy, nitro, cyano or halogen group which connects A1 and A2 and/or A3 and A4 to each other; and when both of B1 and B2 and/or both of B3 and B4 are together -NR12- respectively, two R12s may combine to form a C1-20 divalent hydrocarbon group optionally substituted by a C1-30 hydrocarbon, C1-40 hydrocarbonxy, nitro, cyano or halogen group which connects B1 and B2 and/or B3 and B4 to each other.

  一种在氧化剂存在下通过氧化聚合芳香族化合物生产芳香族化合物聚合物的方法，其中该方法采用(a)由过渡金属络合物组成的催化剂或(b)由过渡金属络合物和活化剂制备的催化剂，所述过渡金属络合物是由以下通式(1-3)表示的钒二核络合物： 其中 A1、A2、A3 和 A4 各自独立地代表氧原子或 NR11，B1、B2、B3 和 B4 各自独立地代表 -O- 或 NR12-； R1、R2、R3、R4、R5、R6、R7 和 R8 各自独立地代表被 C1-50 烷氧基、硝基、氰基或卤素基团任选取代的 C1-30 烃基；或被 C1-50 烷氧基、硝基、氰基或卤素基团任选取代的 C1-40 烃氧基；R9 和 R10 各自独立地代表被 C1-50 烷氧基、硝基、氰基或卤素基团任选取代的 C1-20 亚烷基；或 R9 和 R10 代表任选被 C1-50 烷基、C7-50 芳基、C1-50 烷氧基、硝基、氰基或卤素基团取代的 C6-60 芳烯基团；或 R9 和 R10 代表 -O-、-S--SO2- 或 NR13-；当 R9 和 R10 分别以复数存在时，它们可以相同或不同；m 和 n 各自独立地代表 1 到 7 的整数；R11、R12 和 R13 各自独立地代表氢原子或任选被 C1-50 烷氧基、硝基、氰基或卤素取代的 C1-30 烃基；当 R11、R12 和 R13 分别以复数形式存在时，它们可以相同或不同；当 A1 和 A2 和/或 A3 和 A4 分别都是 NR11 时，两个 R11 可结合形成一个 C1-20 二价烃基，该烃基可选择被 C1-30 烃、C1-40 烃氧基、硝基、氰基或卤素基取代，该烃基将 A1 和 A2 和/或 A3 和 A4 连接在一起；当 B1 和 B2 和/或 B3 和 B4 分别为-NR12-时，两个 R12 可结合形成一个 C1-20 二价烃基，该烃基可选择被 C1-30 烃、C1-40 烃氧基、硝基、氰基或卤素基取代，该烃基将 B1 和 B2 和/或 B3 和 B4 连接在一起。
• Vanadium di-nuclear complex
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2241548A1

  公开（公告）日：2010-10-20

  A vanadium di-nuclear complex represented by the following general formula (1-3): wherein A1, A2, A3 and A4 each independently represent an oxygen atom, or NR11, and B1, B2, B3 and B4 each independently represent -O- or NR12-; R1, R2, R3, R4, R5, R6, R7 and R8 each independently represent a C1-30 hydrocarbon group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; or a C1-40 hydrocarbonoxy group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; R9 and R10 each independently represent a C 1-20 alkylene group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; or R9 and R10 represent a C6-60 arylene group optionally substituted by a C1-50 alkyl, C7-50 aralkyl, C1-50 alkoxy, nitro, cyano or halogen group; or R9 and R10 represent -O-, -S--SO2- or NR13-; and when R9 and R10 exist in a plural number respectively, they may be the same or different; m and n each independently represent an integer of 1 to 7; R11, R12 and R13 each independently represent a hydrogen atom or a C1-30 hydrocarbon group optionally substituted by a C1-50 alkoxy, nitro, cyano or halogen group; when R11, R12 and R13 exist in a plural number respectively, they may be the same or different; when both of A1 and A2 and/or both of A3 and A4 are together NR11 respectively, two R11s may combine to form a C1-20 divalent hydrocarbon group optionally substituted by a C1-30 hydrocarbon, C1-40 hydrocarbonxy, nitro, cyano or halogen group which connects A1 and A2 and/or A3 and A4 to each other; and when both of B1 and B2 and/or both of B3 and B4 are together -NR12- respectively, two R12s may combine to form a C1-20 divalent hydrocarbon group optionally substituted by a C1-30 hydrocarbon, C1-40 hydrocarbonxy, nitro, cyano or halogen group which connects B1 and B2 and/or B3 and B4 to each other.

  由以下通式（1-3）表示的二核钒络合物： 其中 A1、A2、A3 和 A4 各自独立地代表氧原子或 NR11，B1、B2、B3 和 B4 各自独立地代表 -O- 或 NR12-； R1、R2、R3、R4、R5、R6、R7 和 R8 各自独立地代表被 C1-50 烷氧基、硝基、氰基或卤素基团任选取代的 C1-30 烃基；或被 C1-50 烷氧基、硝基、氰基或卤素基团任选取代的 C1-40 烃氧基；R9 和 R10 各自独立地代表被 C1-50 烷氧基、硝基、氰基或卤素基团任选取代的 C 1-20 亚烷基；或 R9 和 R10 代表任选被 C1-50 烷基、C7-50 芳基、C1-50 烷氧基、硝基、氰基或卤素基团取代的 C6-60 芳烯基团；或 R9 和 R10 代表 -O-、-S--SO2- 或 NR13-；当 R9 和 R10 分别以复数存在时，它们可以相同或不同；m 和 n 各自独立地代表 1 到 7 的整数；R11、R12 和 R13 各自独立地代表氢原子或任选被 C1-50 烷氧基、硝基、氰基或卤素取代的 C1-30 烃基；当 R11、R12 和 R13 分别以复数形式存在时，它们可以相同或不同；当 A1 和 A2 和/或 A3 和 A4 分别都是 NR11 时，两个 R11 可结合成一个 C1-20 二价烃基，该烃基可选择被 C1-30 烃、C1-40 烃氧基、硝基、氰基或卤素基取代，该烃基将 A1 和 A2 和/或 A3 和 A4 连接在一起；当 B1 和 B2 和/或 B3 和 B4 分别都是-NR12-时，两个 R12 可结合成一个 C1-20 二价烃基，该烃基可选择被 C1-30 烃、C1-40 烃氧基、硝基、氰基或卤素基取代，该烃基将 B1 和 B2 和/或 B3 和 B4 连接在一起。