1,1'-二甲基-1H,1'H-[2,2']联咪唑 | 37570-94-8

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,1'-二甲基-1H,1'H-[2,2']联咪唑
• 英文名称: 1,1'-dimethyl-2,2'-biimidazole
• 英文别名: N,N'-dimethyl-2,2'-biimidazole；1,1′-dimethyl-1H,1′H-2,2′-biimidazole；bis(1-methyl-imidazol-2-yl)；1,1'-Dimethyl-2,2'-biimidazol；1,1'-Dimethyl-1H,1'H-2,2'-biimidazole；1-methyl-2-(1-methylimidazol-2-yl)imidazole
• CAS: 37570-94-8
• 化学式: C₈H₁₀N₄
• mdl: MFCD00482464
• 分子量: 162.194
• InChiKey: KMRPQHUALQQSPI-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  366.7±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933290090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  应存放在室温、干燥且密封的环境中。

反应信息

• 作为反应物：
  描述：

  1,1'-二甲基-1H,1'H-[2,2']联咪唑 在 AgNO₃ 作用下， 以 水 、 硝酸 、 二甲基亚砜 为溶剂， 生成 [[PtBr(DMSO)]2(Me2bim)]
  参考文献：
  名称：

  Pd(II) and Pt(II) complexes of 2,2′-biimidazole and its N,N′-dimethyl derivative. The crystal structure of [{PtBr(DMSO)}2(Me2bim)] (Me2bim=N,N′-dimethyl-2,2′-biimidazole)

  摘要：

  The complexes [PdCl2(LL)] and [PtX2(LL)] [X = Cl, Br or I; LL = 2,2'-biimidazole (H(2)bim) or N,N'-dimethyl-2,2'-biimidazole (Me(2)bim)] were prepared and characterized spectroscopically. The effects of the chloro compounds on plasmid DNA conformation were studied by electrophoresis in agarose gels, and that of [PtCl2(H(2)bim)] on calf thymus DNA by circular dichroism spectroscopy. The observation that these effects were adversely affected by addition of DMSO (originally used with [PtCl2(Me(2)bim)], to improve its solubility) prompted a study of the solvolysis of [PtCl2(H(2)bim)] by this solvent. H-1 and Pt-195 NMR, and electrospray mass spectra, showed the solvolysis of both Pt-Cl and Pt-N bonds, the release of the ligand H2bim, and the formation of several polynuclear species. X-ray diffractometry of the dinuclear Pt(I) compound [{PtBr(DMSO)}(2)(Me(2)bim)] showed the ligand Me(2)bim to bridge through its non-methylated N atoms between two platinum atoms, the coordination spheres of which were each completed by a Br- ligand, the S atom of a DMSO molecule, and the other Pt atom; the Pt-Pt bond is 2.5560(9) Angstrom in length. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(03)00097-4
• 作为产物：
  描述：

  N-甲基咪唑 在 sodium 5-methyl-2-pyridonate 、 copper(l) chloride 作用下， 以 对二甲苯 为溶剂， 反应 20.0h， 以95%的产率得到1,1'-二甲基-1H,1'H-[2,2']联咪唑
  参考文献：
  名称：

  通过铜（I）/ 2-吡啶酮催化体系的好氧氧化均质偶合，高效合成联唑。

  摘要：

  已经开发了一种高效且方便的CuCl / 2-吡啶酮催化体系，用于氧化制提供双唑产物的吡咯。利用该系统，在非常少量的铜催化剂（1.0摩尔％）的存在下，已经以良好至优异的收率有效地合成了多种联唑。使用空气作为绿色氧化剂是可行的。

  DOI：

  10.1039/c1cc15363c

文献信息

• Mixing divalent ionic liquids: effects of charge and side-chains
  作者：Eduards Bakis、Adriaan van den Bruinhorst、Laure Pison、Ivan Palazzo、Thomas Chang、Marianne Kjellberg、Cameron C. Weber、Margarida Costa Gomes、Tom Welton

  DOI：10.1039/d1cp00208b

  日期：——

  We have prepared novel divalent ionic liquids (ILs) based on the bis(trifluoromethylsulfonyl)imide anion where two charged imidazolium groups in the cations are either directly bound to each other or linked by a single atom. We assessed the influence of the side-chain functionality and divalency on their physical properties and on the thermodynamics of mixing. The results indicate that shortening the

  我们基于双（三氟甲基磺酰基）酰亚胺阴离子制备了新颖的二价离子液体（ILs），其中阳离子中的两个带电咪唑鎓基团彼此直接键合或通过单个原子连接。我们评估了侧链功能和取代度对其物理性质和混合热力学的影响。结果表明，缩短二价IL的间隔基会降低其热稳定性并增加其粘度。二价和一价IL的混合物在混合时显示出与理想情况的微小但显着的偏差。这些偏差似乎主要取决于阳离子侧链的性质和长度的（不匹配）匹配。通过将IL与不同侧链混合而施加的非理想性似乎通过混合物中阳离子形式电荷的增加而增强。
• Highly Efficient, Recyclable Pd(II) Catalysts with Bisimidazole Ligands for the Heck Reaction in Ionic Liquids
  作者：Soon Bong Park、Howard Alper

  DOI：10.1021/ol030071d

  日期：2003.9.1

  [reaction: see text] New Pd(II) complexes with bisimidazole ligands were prepared and proved to be effective catalysts for the Heck reaction under phosphine-free conditions using ionic liquids as solvents. This system could be recycled five times without any loss of catalytic activity.

  [反应：见正文]制备了具有联咪唑配体的新型Pd（II）配合物，并证明是使用离子液体作为溶剂在无膦条件下进行Heck反应的有效催化剂。该系统可以循环使用五次，而不会损失任何催化活性。
• An efficient and convenient Cu(OAc)2/air mediated oxidative coupling of azoles via C–H activation
  作者：Yan Li、Jun Jin、Weixing Qian、Weiliang Bao

  DOI：10.1039/b919396k

  日期：——

  An efficient and convenient approach to construct C–C bonds at the 2-position of azoles via Cu(OAc)2/air mediated oxidative homo- and cross-coupling reaction was reported. The corresponding products were obtained in good to excellent yield.

  报道了一种高效便捷的方法，通过Cu(OAc)2/空气介导的氧化式同偶联和交叉偶联反应，在氮杂环的2-位上构建C-C键。该方法取得了良好至优秀的产率。
• New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles
  作者：Jennifer Kerhervé、Candice Botuha、Joëlle Dubois

  DOI：10.1039/b902601k

  日期：——

  cross-coupling reactions of 2-iodoimidazole have been studied to synthesize imidazole-containing protein farnesyltransferase inhibitors. The Suzuki coupling reaction proved to be very efficient to introduce functionalized alkyl chains at the 2-position of the imidazole ring and a new synthesis of the required alkenylboronates was realised by a reaction of cross metathesis. Asymmetric synthesis of allyl succinic

  钯 的催化交叉偶联反应 2-碘咪唑 已经研究合成 咪唑含蛋白质法呢基转移酶抑制剂。铃木偶联反应被证明非常有效地在咪唑环的2位引入官能化的烷基链，并且通过交叉复分解反应实现了所需烯基硼酸酯的新合成。烯丙基琥珀酸衍生物的不对称合成使我们能够通过Suzuki偶联合成手性蛋白法呢基转移酶抑制剂，并确定我们抑制剂的立体化学对酶活性的影响。
• A Practical Lewis Base Catalyzed Electrophilic Chlorination of Arenes and Heterocycles
  作者：Sean M. Maddox、Christopher J. Nalbandian、Davis E. Smith、Jeffrey L. Gustafson

  DOI：10.1021/acs.orglett.5b00186

  日期：2015.2.20

  mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable

  公开了使用廉价且容易获得的N-卤代琥珀酰亚胺的温和的膦硫化物催化的芳烃和杂环的亲电子卤化。结果表明，该方法可以有效地氯化多种芳烃，包括简单的芳烃（如蒽）和杂环（如吲哚，吡咯并嘧啶和咪唑）。具有路易斯酸性部分的芳烃也被证明是可接受的，强调了该化学反应的温和性质。还发现路易斯碱催化可改善多种多样的芳族溴化反应和碘化反应。