2-isopropyl-1,3,4,5-tetramethylimidazolium iodide | 797791-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-isopropyl-1,3,4,5-tetramethylimidazolium iodide
• CAS: 797791-38-9
• 化学式: C₁₀H₁₉N₂*I
• 分子量: 294.179
• InChiKey: NFSROLHPMLAPQF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-isopropyl-1,3,4,5-tetramethylimidazolium iodide 在 potassium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.25h， 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 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-isopropyl-1,3,4,5-tetramethylimidazolium 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

文献信息

• N-Heterocyclic Olefins as Organocatalysts for Polymerization: Preparation of Well-Defined Poly(propylene oxide)
  作者：Stefan Naumann、Anthony W. Thomas、Andrew P. Dove

  DOI：10.1002/anie.201504175

  日期：2015.8.10

  polymerization of propylene oxide (PO) using a special class of alkene—N‐heterocyclic olefins (NHOs)—as catalysts is described. Manipulation of the chemical structure of the NHO organocatalyst allows for the preparation of the poly(propylene oxide) in high yields with high turnover (TON>2000), which renders this the most active metal‐free system for the polymerization of PO reported to date. The resulting polyether

  描述了使用特殊种类的烯烃-N-杂环烯烃（NHOs）作为催化剂进行的环氧丙烷（PO）的无金属聚合。通过控制NHO有机催化剂的化学结构，可以高收率和高周转率（TON> 2000）制备聚环氧丙烷，这使其成为迄今为止报道的最有效的PO聚合无金属体系。所得到的聚醚显示预测的端基，摩尔质量和低分散度（Đ中号<1.09）。具有不饱和主链的NHO对于发生聚合至关重要，而在环外碳原子处的取代会对反应路径产生影响，并确保抑制副反应。
• Unexpected oxidative C–C cleavage in the metallation of 2-substituted imidazolium salts to give N-heterocyclic carbene complexes
  作者：Anthony R. Chianese、Brian M. Zeglis、Robert H. Crabtree

  DOI：10.1039/b409672j

  日期：——

  Imidazolium salts blocked at C2 with methyl or benzyl groups unexpectedly react with silver oxide to give N-heterocyclic carbene complexes of silver via an oxidative carbon–carbon bond cleavage.

  在 C2 端以甲基或苄基封端的咪唑盐意外地与氧化银发生反应，通过氧化碳碳键裂解生成银的 N-杂环碳烯络合物。
• Controlled preparation of amphiphilic triblock-copolyether in a metal- and solvent-free approach for tailored structure-directing agents
  作者：Alexander Balint、Marius Papendick、Manuel Clauss、Carsten Müller、Frank Giesselmann、Stefan Naumann

  DOI：10.1039/c7cc09031e

  日期：——

  Organocatalysis is employed as a precise tool for the preparation of triblock-copolyethers for a systematic access to structure-direction.

  有机催化被用作一种精确工具，用于制备三嵌段共聚醚，以实现对结构定向的系统性访问。
• Lewis Pair Polymerization of Epoxides via Zwitterionic Species as a Route to High‐Molar‐Mass Polyethers
  作者：Patrick Walther、Annabelle Krauß、Stefan Naumann

  DOI：10.1002/anie.201904806

  日期：2019.7.29

  used to prepare poly(propylene oxide) with a molar mass (Mn) >500 000 g mol−1, in some cases even >106 g mol−1, as determined by GPC/light scattering. This is achieved by combining the rapid polymerization characteristics of a zwitterionic, Lewis pair type mechanism with the efficient epoxide activation by the MgII species. Transfer‐to‐monomer, traditionally frustrating attempts at synthesizing polyethers

  使用基于N杂环烯烃（NHOs）和双（六甲基二硅叠氮化镁）（Mg（HMDS）2）的双催化装置制备摩尔质量（M n）> 500 000 g mol -1的聚环氧丙烷通过GPC /光散射测定，在某些情况下甚至大于10 6  g mol -1。这是通过将两性离子路易斯对型机理的快速聚合特性与Mg II的有效环氧化物活化相结合而实现的物种。传统上阻碍合成高聚合度的聚醚的传统尝试是转移单体，但实际上已被这种方法作为限制因素而取消。NMR和MALDI-ToF MS实验揭示了所提出机制的关键方面，由此聚合反应是由NHO通过对活化单体的亲核攻击而引发的，从而生成两性离子物质。该策略也可以扩展到其他环氧化物，包括功能化单体。