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1H-Imidazolium, 1-butyl-3-(2-pyridinylmethyl)-, bromide | 468081-83-6

中文名称
——
中文别名
——
英文名称
1H-Imidazolium, 1-butyl-3-(2-pyridinylmethyl)-, bromide
英文别名
N-butyl-N'-(2-pyridylmethyl)imidazolium bromide;3-n-butyl-1-(2-picolyl)imidazolium bromide;1-butyl-3-(2-picolyl)imidazolium bromide
1H-Imidazolium, 1-butyl-3-(2-pyridinylmethyl)-, bromide化学式
CAS
468081-83-6
化学式
Br*C13H18N3
mdl
——
分子量
296.21
InChiKey
JPEPUGBOEYQOMI-UHFFFAOYSA-M
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    -0.98
  • 重原子数:
    17.0
  • 可旋转键数:
    5.0
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.38
  • 拓扑面积:
    21.7
  • 氢给体数:
    0.0
  • 氢受体数:
    2.0

反应信息

  • 作为反应物:
    描述:
    1H-Imidazolium, 1-butyl-3-(2-pyridinylmethyl)-, bromide 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 在 Ag2O 作用下, 以 二氯甲烷 为溶剂, 以70%的产率得到[N-n-butyl-N'-(2-pyridylmethyl)imidazole-2-ylidene](1,5-cycooctadiene)rhodium(I) chloride
    参考文献:
    名称:
    吡啶官能化的N-杂环卡宾的配位通用性:不同激活程序的详细研究。新型Rh和Ir化合物的表征及其催化活性的研究。
    摘要:
    用于配位Nn-丁基-N'-(2-吡啶基甲基)咪唑鎓盐的三种不同的反应程序产生了Rh和Ir的新的N-杂环配合物。咪唑鎓盐与[IrCl(cod)](2)的直接反应提供了NHC-Ir(III)-H配合物,而银-NHC配合物的重金属化和NEt(3)的去质子化得到了新的M的NHC配合物(I)和M(III)与[MCl(cod)](2)或[MCl(coe)(2)](2)反应时(M = Rh,Ir)。描述了双卡宾Rh(III)和Ir(III)配合物的晶体结构。已在乙炔的氢化硅烷化,炔属羧酸的环化以及氢向酮的转移中测试了所获得化合物的催化性能。
    DOI:
    10.1021/ic051272b
  • 作为产物:
    描述:
    2-溴甲基吡啶N-丁基咪唑甲醇 为溶剂, 反应 12.0h, 以95%的产率得到1H-Imidazolium, 1-butyl-3-(2-pyridinylmethyl)-, bromide
    参考文献:
    名称:
    在咪唑盐与 IrH5(PPh3)2 反应中,C-H 活化机制的变化导致选择性的阴离子依赖性开关
    摘要:
    改变 Br、BF4、PF6、SbF6 在其离子对 2-吡啶甲基咪唑鎓盐中的抗衡阴离子会导致与 IrH5(PPh3)2 的动力学反应产物从螯合 N-杂环卡宾 (NHCs) 转换为具有正常 C2 (N路径)到异常 C5 绑定(AN 路径)。计算工作 (DFT) 表明 AN 路径涉及 CH 氧化加成到 Ir(III) 以产生 Ir(V),而阴离子依赖性很小。相比之下,N 路径通过异裂 CH 激活,质子转移到相邻的氢化物。转移的质子伴随着阴离子耦合质子转移中的抗衡阴离子,导致 N 路径的阴离子依赖性,从而导致 N/AN 选择性。N 路径通过 Ir(III),而不是 Ir(V),因为正常 NHC 是比异常 NHC 强得多的供体配体。PGSE NMR 实验支持在反应物和产物中形成离子对。19F,1H-HOESY NMR 实验表明产物的离子对结构与计算预测(ONIOM(B3PW91/UFF))一致。
    DOI:
    10.1021/ja055317j
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文献信息

  • Synthesis, structures and catalytic activities of ruthenium(ii) carbonyl chloride complexes containing pyridine-functionalised N-heterocyclic carbenes
    作者:Yong Cheng、Hui-Jun Xu、Jia-Feng Sun、Yi-Zhi Li、Xue-Tai Chen、Zi-Ling Xue
    DOI:10.1039/b904882k
    日期:——
    A series of ruthenium(II) carbonyl chloride complexes with pyridine-functionalised N-heterocyclic carbenes, trans(Cl)- and cis(Cl)-[Ru(Py–NHC)(CO)2Cl2] [Py–NHC = 3-tert-butyl-1-(2-pyridyl)imidazol-2-ylidene, 1a and 1b; 3-n-butyl-1-(2-pyridyl)imidazol-2-ylidene, 2a and 2b; 3-tert-butyl-1-picolylimidazol-2-ylidene, 3a and 3b; 3-n-butyl-1-picolylimidazol-2-ylidene, 4a and 4b; 3-benzyl-1-picolylimidazol-2-ylidene
    一系列(II)羰基配合物与吡啶功能化 N-杂环卡宾,反式(Cl)-和顺式(Cl)-[Ru(Py–NHC)(CO)2 Cl 2 ] [Py–NHC = 3-叔丁基-1-(2-吡啶基)咪唑-2-亚乙基,1a和1b ; 3 - n-丁基-1-(2-吡啶基)咪唑-2-亚烷基,2a和2b ; 3-叔丁基-1-吡咯咪唑-2-亚烷基,3a和3b ; 3-正丁基-1-甲基吡啶咪唑-2-亚烷基,4a和4b;m / z 。通过以下方法制备了3-苄基-1-吡啶咪唑-2-亚烷基5a和5b。属化由相应的卡宾配合物得到,并通过元素分析,红外光谱和1 H和13 C NMR光谱进行表征。的收率的反式(CL) -和顺式(CL) -异构体可以通过改变反应条件来控制:将反式异构体进行动力学形成为主要产品在60-70%产率的CH 22在环境温度下,而热力学上的顺式异构体是主要产物,收率70-80%。甲苯在回流温度下。通过在衬有特龙的不锈钢中的CH
  • Basic Ionic Liquids: Facile Solvents for Carbon–Carbon Bond Formation Reactions and Ready Access to Palladium Nanoparticles
    作者:Chengfeng Ye、Ji-Chang Xiao、Brendan Twamley、Aaron D. LaLonde、M. Grant Norton、Jean'ne M. Shreeve
    DOI:10.1002/ejoc.200700502
    日期:2007.10
    A basic ionic liquid was selected to serve as both the solvent and base for Heck, “copper-free” Sonogashira reactions, and for homocoupling reactions of terminal alkynes. The ionic liquids with tertiary aliphatic amines are effective solvents for these reactions. Under reflux conditions, eight equivalent basic ionic liquids and Pd(OAc)2 in THF or acetone produced palladium colloids with diameters of
    选择碱性离子液体作为 Heck、“无” Sonogashira 反应和末端炔烃的均偶联反应的溶剂和碱。含有叔脂肪胺的离子液体是这些反应的有效溶剂。在回流条件下,八当量碱性离子液体和 Pd(OAc)2 在 THF 或丙酮中分别产生直径为 (2.6 ± 0.3) 或 (3.7 ± 0.5) nm 的胶体。还报告了 Knoevenagel 缩合的初步结果。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
  • Abnormal Ligand Binding and Reversible Ring Hydrogenation in the Reaction of Imidazolium Salts with IrH<sub>5</sub>(PPh<sub>3</sub>)<sub>2</sub>
    作者:Stephan Gründemann、Anes Kovacevic、Martin Albrecht、Jack W. Faller、Robert H. Crabtree
    DOI:10.1021/ja026735g
    日期:2002.9.1
    We show that imidazolium salts do not always give normal or even aromatic carbenes on metalation, and the chemistry of these ligands can be much more complicated than previously thought. N,N'-disubstituted imidazolium salts of type [(2-py)(CH2)(n)(C3H3N2)R]BF4 react with IrH5(PPh3)(2) to give N,C-chelated products (n = 0, 1; 2-py = 2-pyridyl; C(3)H(3)N2 = imidazolium; R = mesityl, n-butyl, i-propyl, methyl). Depending on the circumstances, three types of kinetic products can be formed: in one, the imidazole metalation site is the normal C2 as expected; in another, the metalation occurs at the abnormal C4 site; and in the third, C4 metalation is accompanied by hydrogenation of the imidazolium ring. The bonding mode is confirmed by structural studies, and spectroscopic criteria can also distinguish the cases. Initial hydrogen transfer can take place from the metal to the carbene to give the imidazolium ring hydrogenation product, as shown by isotope labeling; this hydrogen transfer proves reversible on reflux when the abnormal aromatic carbene is obtained as final product. Care may therefore be needed in the future in verifying the structure(s) formed in cases where a catalyst is generated in situ from imidazolium salt and metal precursor.
  • R-Allyl Nickel(II) Complexes with Chelating N-Heterocyclic Carbenes: Synthesis, Structural Characterization, and Catalytic Activity
    作者:Lourdes Benı́tez Junquera、M. Carmen Puerta、Pedro Valerga
    DOI:10.1021/om200937d
    日期:2012.3.26
    The N-heterocyclic carbene (NHC) nickel complexes [(L)Ni(NHC)][BAr4F] (Ar-F = 3,5-bis(trifluoromethyl)-phenyl; L = allyl (1), methylallyl (2); NHC = 1-(2-picolyl)-3-methylimidazol-2-ylidene (a), 1-(2-picolyl)-3-isopropylimidazol-2-ylidene (b), 1-(2-picolyl)-3-n-butylimidazol-2-ylidene (c), 1-(2-picolyl)-3-phenylimidazol-2-ylidene (d), 1-(2-picolyl)-3-methylbenzoimidazol-2-ylidene (e), 1-(2-picolyl)-4,5-dichloro-3-methylimidazol-2-ylidene (0) have been obtained in high yields and characterized by NMR spectroscopy. Furthermore, Id was unambiguously characterized by single-crystal X-ray crystallography. Complexes 1a-f/2a-f have shown catalytic activity toward dimerization and hydrosilylation of styrenes. In particular, 1a proved to be the most efficient catalyst in the dimerization of styrene derivatives in the absence of cocatalyst. Also, complexes 1a,d showed high selectivity and moderate to good yields in hydrosilylation reactions.
  • Syntheses, Structures, and Catalytic Properties of Ruthenium(II) Nitrosyl Complexes with Pyridine-Functionalized N-Heterocyclic Carbenes
    作者:Yong Cheng、Jia-Feng Sun、Hong-Ling Yang、Hui-Jun Xu、Yi-Zhi Li、Xue-Tai Chen、Zi-Ling Xue
    DOI:10.1021/om800791n
    日期:2009.2.9
    Ruthenium(II) nitrosyl complexes with pyridine-functionalized N-heterocyclic carbenes [(L)Ru(NO)Cl-3] [L = 3-tert-butyl-1-(2-pyridyl)imidazol-2-ylidene, 2a; 3-n-butyl-1-(2-pyridyl)imidazol-2-ylidene, 2b; 3-tert-butyl-1-picolylimidazol-2-ylidene, 2c; 3-n-butyl-1-picolylimidazol-2-ylidene, 2d; and 3-benzyl-1-pico-lylimidazol-2-ylidene, 2e] have been prepared by transmetalation from the corresponding silver carbene complexes. Compounds 2a-c have been characterized by single-crystal X-ray crystallography. Compounds 2a-e show catalytic activities in transfer hydrogenation of ketones.
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