N,N-bis((3,5-dimethylpyrazol-1-yl)methyl)aniline | 85264-36-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis((3,5-dimethylpyrazol-1-yl)methyl)aniline
• 英文别名: N,N-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl)aniline；3,5,5'-tetramethyl-N,N-Bis(pyrazol-1-ylmethyl)aniline；N,N-bis[(3,5-dimethylpyrazol-1-yl)methyl]aniline
• CAS: 85264-36-4
• 化学式: C₁₈H₂₃N₅
• 分子量: 309.414
• InChiKey: WRZCLCMIUFQVFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-bis((3,5-dimethylpyrazol-1-yl)methyl)aniline 、 zinc(II) chloride 以 乙醇 为溶剂， 以73%的产率得到N,N-bis(3,5-dimethyl-1H-pyrazolyl-1-methyl)aniline zinc(II) chloride
  参考文献：
  名称：

  Synthesis and X-ray crystal structure of derivatives from the N,N-bis(1H-pyrazolyl-1-methyl)aniline(dichloro)Zn(II) complex: Substituent effects on the phenyl ring versus the pyrazole ring

  摘要：

  The reaction of anhydrous ZnCl2 with ancillary ligands, including N,N-bis(1H-pyrazolyl-1-methyl)aniline (L-1), N,N-bis(1H-pyrazolyl-1-methyl)-p-methoxyaniline (L-2), N,N-bis(1H-pyrazolyl-1-methyl)-p-fluoro-aniline (L-3) and N,N-bis(3,5-dimethyl-1H-pyrazolyl-1-methyl)aniline (L-4), in ethanol yields Zn(II) chloride complexes, i.e., L1ZnCl2, L2ZnCl2, L3ZnCl2 and L4ZnCl2. X-ray crystallographic analysis revealed that the Zn atoms of all of the synthesized complexes have a distorted tetrahedral geometry involving a nitrogen atom from each of two pyrazole groups and two chloro ligands. However, the nitrogen atom of the aniline group is not coordinated to the Zn center, resulting in the formation of an eight-membered chelate ring. The catalytic activity of the Zn(II) complexes in the polymerization of methyl methacrylate (MMA) in the presence of modified methylaluminoxane (MMAO) results in a higher molecular weight and a narrow polydispersity index (PDI) range. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.05.014
• 作为产物：
  描述：

  3,5-二甲基吡唑 在 乙醇 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 N,N-bis((3,5-dimethylpyrazol-1-yl)methyl)aniline
  参考文献：
  名称：

  One Pot Synthesis and In Vitro Antitumor Activity of some Bipyrazolic Tripodal Derivatives

  摘要：

  本文首次报道了单吡唑和双吡唑三元衍生物的合成和结构-活性关系（SAR）抗肿瘤活性。这十种产品针对三种人类癌症细胞系进行了测试，包括乳腺癌（MDA-MB231）、前列腺癌（PC3）和结直肠癌（LoVo）。在双吡唑系列中，大多数产品对三种人类癌细胞株具有中等程度的抗肿瘤活性，结直肠癌的抗肿瘤活性为 5 7 8，乳腺癌和前列腺癌的抗肿瘤活性为 5 7 ≉ 8。

  DOI：

  10.2174/157018012799129792

文献信息

• Synthesis of N,N′-bis and N,N,N′,N′-tetra-[(3,5-di-substituted-1-pyrazolyl)methyl]para-phenylenediamines: new candidate ligands for metal complex wires
  作者：Maria Daoudi、Najib Ben Larbi、Abdelali Kerbal、Brahim Bennani、Jean-Pierre Launay、Jacques Bonvoisin、Taibi Ben Hadda、Pierre H. Dixneuf

  DOI：10.1016/j.tet.2006.01.034

  日期：2006.3

  A series of tridentate ligands N,N-bis-[(di-substituted-1-pyrazolyl)methyl]arylamines 2–3a,b and benzylamine 4a,b, tetradentate N,N′-bis-[(di-substituted-1-pyrazolyl)methyl]para-phenylenediamines 7a,b and hexadentate N,N,N′,N′-tetra-[(di-substituted-1-pyrazolyl)methyl]para-phenylenediamines 8a,b has been prepared in good yield by condensation of arylamines, benzylamine or para-phenylenediamine with

  一系列三齿配体的Ñ，ñ -双- [（二取代-1-吡唑基）甲基]芳基胺2 -图3a，b和苄图4a，b，四齿Ñ，Ñ ' -双- [（二取代-1- -（吡唑基）甲基]对苯二胺7a，b和六齿的N，N，N '，N'-四-[（二取代-1-吡唑基）甲基]对苯二胺8a，b通过芳基胺，苄基胺或对苯二胺与N-羟甲基二取代的吡唑1a，b的缩合，可以高收率制备α-己内酰胺。描述了这些各种多齿配体的合成和表征。
• Solid-state detection of gases by use of thin films based on pyrazole units, and morphological characterization of the films by AFM
  作者：R. Touzani、S. El Kadiri、A. Zerrouki、G. Vasapollo、S. Scorrano、R. Del Sole、M. G. Manera、R. Rella

  DOI：10.1007/s11164-012-0541-x

  日期：2012.11

  Synthesis of a series of heterocyclic compounds based on pyrazole units is reported. The possibility of using these compounds, as solid-state thin layers deposited on quartz substrates, for optical recognition of hazardous pollutant gases was investigated. The gases SO2, NO2, CO, CH4, and NH3 were studied. Two of the ligand layers had reversible sensitivity toward SO2, with good reaction time. The presence of CO, CH4 NO2, and NH3 had no effect on the optical properties. Morphological characterization by use of AFM microscopy was also investigated.

  报道了基于吡唑单元的系列杂环化合物的合成。研究了这些化合物作为沉积在石英基板上的固态薄层，用于危险污染物气体的光学识别的可能性。研究了SO2、NO2、CO、CH4和NH3气体。其中两种配体层对SO2具有可逆敏感性，反应时间良好。CO、CH4、NO2和NH3的存在对光学性质没有影响。还通过AFM显微镜进行了形态学表征研究。
• X‐ray crystal structures and MMA polymerization of cadmium(II) complexes with bidentate pyrazole ligands: the formation of monomers or dimers as a function of a methyl substituent on the pyrazole and aniline rings
  作者：Dongil Kim、Sunghoon Kim、Hyun Yul Woo、Ha‐Jin Lee、Hyosun Lee

  DOI：10.1002/aoc.3148

  日期：2014.6

  N,N‐bis(1H‐pyrazolyl‐1‐methyl)aniline (L1), N,N‐bis(1H‐pyrazolyl‐1‐methyl)‐p‐methylaniline (L2), N,N‐bis(1H‐pyrazolyl‐1‐methyl)‐3,5‐dimethylaniline (L3), N,N‐bis(3,5‐dimethyl‐1H‐pyrazolyl‐1‐methyl)aniline (L4) and N,N‐bis(1H‐pyrazolyl‐1‐methyl)‐2,6‐dimethylaniline (L5) in ethanol yields novel Cd(II) bromide complexes, [L1CdBr2]2, [L2CdBr2]2, [L3CdBr2]2, [L4CdBr2] and [L5CdBr2]. The X‐ray crystal structures

  CdBr 2 ·4H 2 O与辅助配体N，N-双（1 H-吡唑基-1-甲基）苯胺（L 1），N，N-双（1 H-吡唑基-1-甲基）-反应对甲基苯胺（L 2），N，N-双（1 H-吡唑基-1-甲基）-3,5-二甲基苯胺（L 3），N，N-双（3,5-二甲基-1 H-吡唑基-1-甲基苯胺（L 4）和N，N-双（1 H-吡唑基-1-甲基）-2,6-二甲基苯胺（L 5）在乙醇中生成新型Cd（II）溴化物配合物[L 1 CdBr 2 ] 2，[L 2 CdBr 2 ] 2，[L 3 CdBr 2 ] 2，[L 4 CdBr 2 ]和[L 5 CdBr 2 ]。[L 1 CdBr 2 ] 2，[L 2的X射线晶体结构CdBr 2 ] 2和[L 3 CdBr 2 ] 2揭示了一种具有晶体学反演对称性的溴桥联二聚体。相反，[L 4 CdBr 2 ]和[L 5 CdBr 2 ]作为单体络合物存在，可能是由于[L
• Copper(II) complexes containing N′-aromatic group substituted N,N′,N-bis((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amines: Synthesis, structures, polymerization of methyl methacrylate and ring opening polymerization of rac-lactide
  作者：Hyungwoo Cho、Solhye Choe、Dongil Kim、Hyosun Lee、Saira Nayab

  DOI：10.1016/j.poly.2020.114641

  日期：2020.9

  Abstract A series of Cu(II) complexes, [LnCuCl2] (Ln = LA–LF), supported by N′-aromatic-group-substituted N,N-bis((3,5-dimethyl-1H-pyrazol-1-yl)methylamine ligands have been synthesized. Variations of substituents at the ortho position of the aniline moiety influenced the solid-state structures of these complexes. The X-ray structures of [LnCuCl2] (Ln = LA–LC and LF) revealed that ligands are coordinated

  富含Syndio的PMMA的多分散指数（PDI）略宽。另外，原位产生的二甲基衍生物，聚合的rac-LA和在室温下为PLA提供了中等的杂规度。重要的是，已发现所研究的Cu（II）配合物的催化效率受配体的空间和电子性质的影响。
• Polymerizations of methyl methacrylate and rac-lactide by 4-coordinate cobalt(II) complexes supported by N′-substituted N,N′,N-bis((1H-pyrazol-1-yl)methyl)amine derivatives
  作者：Sujin Shin、Saira Nayab、Hyosun Lee

  DOI：10.1016/j.poly.2017.12.021

  日期：2018.2

  -1-yl)methyl)-4-fluoroaniline (LH), have been synthesized and structurally characterized. The molecular structures of these Co(II) complexes showed a distorted tetrahedral geometry. No interaction exists between the Namine atom and the Co(II) centre in the [LnCoCl2] complexes, thus resulting in the formation of an eight membered chelate ring. [LDCoCl2] exhibited the highest catalytic activity (4.0

  因此导致形成八元螯合环。[LDCoCl2]在60°C的改性甲基铝氧烷（MMAO）存在下，对于甲基丙烯酸甲酯（MMA）的聚合反应表现出最高的催化活性（4.02×104 g PMMA / molCo h），并生成具有高分子量（Mw）（10.5×105 g / mol）。在123–130°C的温度范围内获得了富含间规的PMMA。在本研究中，配合物的MMA聚合活性不应仅视为金属中心周围配体的总位阻的函数。原位生成的二甲基衍生物[LnCoMe2]（Ln = LA-LH）有效地聚合了rac-丙交酯（rac-LA），并得到了具有良好的数均分子量和较窄的多分散指数（PDI）的聚丙交酯（PLA）。这些二甲基钴引发剂中金属中心周围的电子密度似乎增强了活性，而立体选择性受到了负面影响。因此，吡唑环部分中是否存在甲基不仅影响MMA聚合中Co（II）配合物的活性，而且影响rac-LA的ROP中Co（II）引发剂的立体选择性。