1,2,3,4,5-pentamethyl-1H-imidazol-3-ium iodide | 25812-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2,3,4,5-pentamethyl-1H-imidazol-3-ium iodide
• 英文别名: 1,2,3,4,5-Pentamethylimidazolium iodide；1,2,3,4,5-pentamethylimidazol-1-ium;iodide
• CAS: 25812-77-5
• 化学式: C₈H₁₅N₂*I
• 分子量: 266.125
• InChiKey: CUSBUYBCKPFTHE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.22
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4,5-pentamethyl-1H-imidazol-3-ium iodide 在 potassium hydride 作用下， 以 正己烷 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Preparation of 2‐Alkylidene‐Substituted 1,3,4,5‐Tetramethylimidazolines and Their Reactivity Towards Rh ^I Complexes and B(C ₆ F ₅ ) ₃

  摘要：

  AbstractIn addition to the known 1,3,4,5‐tetramethyl‐2‐methyleneimidazoline (1a), which exhibits a highly polarized exocyclic C–C bond, a series of novel 2‐alkylidene‐substituted 1,3,4,5‐tetramethylimidazolines 1b–e were synthesized and characterized. The molecular structures of 1b, 1d, and 1e were determined by X‐ray diffraction analysis and revealed an increase in the polarization of the exocyclic C–C bond with increasing steric demand of the 2‐substituent. On the basis of their ylidic nature, 1a–e show enhanced basicity and reactivity towards Lewis acidic centers. Treatment of 1a and 1b with [{RhCl(cod)}2] or B(C6F5)3 afforded complexes of the type [(L)RhCl(cod)] (4a,b), [(L)RhCl(CO)2] (7a,b) (L = 1a,b) or classical Lewis acid/base adducts [(1a)B(C6F5)3] (8a) and [(1b)B(C6F5)3] (8b). In contrast, complexes [(L)RhCl(cod)] with 1c and 1d as ligands are not stable, and imidazolium dichlororhodate salts 6a and 6b were isolated instead. Rhodium–alkyl complexes 5a and 5b are assumed to be intermediates in this decomposition process, and 5a was characterized by X‐ray diffraction analysis. Furthermore, treatment of 1c and 1d with B(C6F5)3 did not afford classical Lewis adducts, and instead imidazolium hydridoborate salts 9a and 9b are formed by hydride abstraction. Surprisingly, we found that 1e does not react with [{RhCl(cod)}2] and forms an abnormal Lewis adduct 10 when treated with B(C6F5)3.

  DOI：

  10.1002/ejic.201201516
• 作为产物：
  描述：

  1,4,5-三甲基-1H-咪唑 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1,2,3,4,5-pentamethyl-1H-imidazol-3-ium iodide
  参考文献：
  名称：

  N-杂环烯烃作为碱促进烷基化反应的高效相转移催化剂

  摘要：

  N-杂环烯烃（NHOs）由于其强大的Bronsted / Lewis基础性，最近已成为多种化学反应的有效促进剂。在这里，我们将NHO的新颖应用报告为高效...

  DOI：

  10.1039/c6cc03771b
• 作为试剂：
  描述：

  2-吡啶甲酸甲酯 、 乙醇 在 1,2,3,4,5-pentamethyl-1H-imidazol-3-ium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到2-吡啶甲酸乙酯
  参考文献：
  名称：

  N-杂环烯烃催化酯交换反应的开发与应用

  摘要：

  已经开发出一种利用N-杂环卡宾的亚烷基衍生物N-杂环烯烃（NHO）作为有机催化剂来促进酯交换反应的新方法。由于其强大的Brønsted/ Lewis碱性，NHO可以增强醇与羧酸酯的酰化反应的亲核性。这种转化可用于与工业相关的过程中，例如生产生物柴油，从塑料瓶中解聚聚对苯二甲酸乙二醇酯（PET）以便回收利用，以及环酯的开环聚合以形成可生物降解的聚合物，例如聚丙交酯（PLA）和聚己内酯（PCL）。

  DOI：

  10.1021/acs.orglett.6b00835

文献信息

• Brönsted Basicities and Nucleophilicities of N-Heterocyclic Olefins in Solution: N-Heterocyclic Carbene versus N-Heterocyclic Olefin. Which Is More Basic, and Which Is More Nucleophilic?
  作者：Zhen Li、Pengju Ji、Jin-Pei Cheng

  DOI：10.1021/acs.joc.0c02838

  日期：2021.2.5

  common reference electrophiles for quantifying nucleophilic reactivities. In general, the nucleophilicity of the NHOs is much stronger than that of commonly used Lewis bases such as Ph3P or DMAP [4-(dimethylamino)pyridine] but weaker than that of their NHC analogues; however, caution should be taken when generalizing this conclusion to a wide range of electrophiles with distinctively electronic and structural

  通过使用紫外可见光谱法测量相应的前体在DMSO中的平衡酸度，建立了包含9种代表性N-杂环烯烃（NHO）的布朗斯台德碱度标度。基本性（p K aH被调查的NHO的s）范围从14.7到24.1。不饱和NHO的碱性比其N-杂环卡宾（NHC）类似物的碱性强。但是，饱和盐的碱度比其NHC类似物的碱度弱得多，这在很大程度上是由于芳香化作用本质上影响NHC和NHO前体的酸离解。通过监测这些NHO与常用参比亲电试剂的反应动力学来光度法测量四个NHO的亲核性，以定量亲核反应性。通常，NHO的亲核性比常用的路易斯碱（例如Ph 3）强得多P或DMAP [4-（二甲氨基）吡啶]，但比其NHC类似物弱；然而，将这一结论推广到具有明显电子和结构特性的各种亲电子试剂时，应谨慎行事。
• Anisotropic, Organic Ionic Plastic Crystal Mesophases from Persubstituted Imidazolium Pentacyanocyclopentadienide Salts
  作者：Karel Goossens、Lena Rakers、Benoît Heinrich、Guillermo Ahumada、Takahiro Ichikawa、Bertrand Donnio、Tae Joo Shin、Christopher W. Bielawski、Frank Glorius

  DOI：10.1021/acs.chemmater.9b02338

  日期：2019.12.10

  pentacyanocyclopentadienide ([Cp(CN)5]−) counterions. Salts containing relatively small anions were obtained as low-melting solids, whereas those with [Cp(CN)5]− anions were found to be ionic liquids even below room temperature. A permethylated derivative, [(C1)5im][Cp(CN)5], proved to be exceptional. Upon heating, the salt self-organized into a new type of organic ionic plastic crystal (OIPC) mesophase, which was

  我们描述的合成，超分子组织，和对称1,2,3,4,5- pentaalkylimidazolium空前家族的热特性（[（C Ñ）5 IM] +）配备有卤化物，硝酸盐或pentacyanocyclopentadienide（[盐Cp（CN）5 ] -）抗衡离子。获得了包含相对较小阴离子的盐，为低熔点固体，而发现具有[Cp（CN）5 ] -阴离子的盐甚至在室温以下仍为离子液体。全甲基化衍生物，[（C 1）5 im] [Cp（CN）5]，被证明是例外。加热后，该盐自组织成新型有机离子塑料晶体（OIPC）中间相，称为M hex，其各向异性结构具有六边形有序旋转的阴离子叠层，该叠层位于由无序阳离子组成的连续区内。尽管没有长而柔性的链，中间相的结构类似于经典的柱状液晶相。在M十六进制中相中，阴离子柱周围的阳离子有效地发挥了“软化”结构成分的作用，与挠性链的作用方式大致相同。新型中间相的发现显示了二维的
• Synthesis, Properties, and Structures of Salts with the Reineckate Anion, [CrIII(NCS)4(NH3)2]-, and Large Organic Cations
  作者：Tim Peppel、Christin Schmidt、Martin Köckerling

  DOI：10.1002/zaac.201100091

  日期：2011.8

  measurements: (nBu4N)[Cr(NCS)4(NH3)2]: monoclinic, C2/c (no. 15), a = 12.0818(8), b = 10.2425(8), c = 24.222(2) A, β = 98.324(3)°, Z = 4, R1(F)/wR2(F2) = 0.0332/0.0871; (C12H25)4N}[Cr(NCS)4(NH3)2]·0.85H2O: triclinic, P (no. 2), a = 8.4049(1), b = 20.1525(4), c = 20.7908(4) A, α = 67.487(1)°, β = 81.328(1)°, γ = 78.040(1)°, Z = 2, R1(F)/wR2(F2) = 0.0533/0.1343; (EMIm)[Cr(NCS)4(NH3)2]: orthorhombic, Pbcm (no

  一系列 9 种新型 Reineckate 盐，A[CrIII(NCS)4(NH3)2] 与各种大有机阳离子 A = 四烷基铵，[R4N]+，R = 正丁基，正十二烷基；1-烷基-3-甲基咪唑鎓，(RMIm)+：R = 甲基、乙基、异丙基、正丁基和正己基；合成了 A = 1,3-二甲基-2,4,5-三苯基咪唑鎓和 A = 1,2,3,4,5-五甲基咪唑鎓。测量每种化合物的熔点以查看是否有任何属于具有低熔点的含金属离子液体组。通过元素分析、NMR、IR和UV/Vis光谱进一步表征每种化合物。使用 Evans 方法从 NMR 研究得出有关磁行为的信息。已经发现，每种化合物都是顺磁性的，具有仅自旋 CrIII 的有效磁矩。具有 A = 四正丁基铵的 Reineckates 的结构，四正十二烷基铵、1-乙基-3-甲基咪唑鎓和 1,2,3,4,5-五甲基咪唑鎓通过单晶 X 射线衍射测量测定：(nBu4N)[Cr(NCS)4(
• Continuous carbonylation process
  申请人：——

  公开号：US20030212295A1

  公开（公告）日：2003-11-13

  Disclosed is a continuous process wherein carbon monoxide, a carbonylatable reactant, and a halide in the gas phase are contacted with a non-volatile catalyst solution comprising an ionic liquid and a Group VIII metal to produce a carbonylation product in the gas phase. The process is useful for the continuous preparation of acetic acid by the carbonylation of methanol.

  披露了一种连续过程，其中一种可与羰基化反应的反应物一氧化碳和气相中的卤化物与一种非挥发性催化剂溶液接触，该溶液包括一种离子液体和一种第VIII族金属，以在气相中产生羰基化产物。该过程可用于通过对甲醇进行羰基化来连续制备醋酸。
• Synthesis of RTH-Type Zeolites Using a Diverse Library of Imidazolium Cations
  作者：Joel E. Schmidt、Mark A. Deimund、Dan Xie、Mark E. Davis

  DOI：10.1021/acs.chemmater.5b01003

  日期：2015.5.26

  RTH-type zeolites are promising catalytic materials for applications that include the important methanol-to-olefins (MTO) and NOX reduction reactions. Here, RTH-type zeolites are prepared using a wide-range of imidazolium-based, cationic organic structure directing agents (OSDAs), that greatly expand the methodologies and compositions that can be used to synthesize these materials. The abilities of the OSDAs to produce RTH-type zeolites agree well with results from molecular modeling studies of predicted stabilization energies of the OSDAs in the RTH framework. The RTH-type zeolites are stable to steaming up to 900 °C and are shown to be active MTO catalysts.

  RTH型沸石是有前途的催化材料，适用于包括重要的甲醇转烯（MTO）和氮氧化物（NOX）还原反应在内的应用。这里，使用广泛的咪唑鎓基阳离子有机结构导向剂（OSDAs）制备RTH型沸石，这大大扩展了合成这些材料的 methodologies 和成分。OSDAs 产生 RTH 型沸石的能力与分子模拟研究中预计的 OSDAs 在 RTH 框架中的稳定化能结果相符。RTH 型沸石在蒸汽环境中稳定至 900 °C，并且被证明是有效的 MTO 催化剂。