1-isopropyl-2,3-dimethylimidazolium iodide | 425603-66-3

• 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-isopropyl-2,3-dimethylimidazolium iodide
• 英文别名: 1,2-Dimethyl-3-propan-2-ylimidazol-1-ium;iodide；1,2-dimethyl-3-propan-2-ylimidazol-1-ium;iodide
• CAS: 425603-66-3
• 化学式: C₈H₁₅N₂*I
• 分子量: 266.125
• InChiKey: FMHJDPZBLLIZSJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.79
• 重原子数：
  11
• 可旋转键数：
  1
• 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-isopropyl-2,3-dimethylimidazolium iodide 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 2-(3-isopropyl-1-methyl-1H-imidazol-3-ium-2-yl)acetate
  参考文献：
  名称：

  Fast CO₂ Sequestration, Activation, and Catalytic Transformation Using N-Heterocyclic Olefins

  摘要：

  N-Heterocyclic Olefin (NHO) with high electronegativity at the terminal carbon atom was found to show a strong tendency for CO2 sequestration, affording a CO2 adduct (NHO-CO2). X-ray single crystal analysis revealed the bent geometry of the binding CO2 in the NHO-CO2 adducts with an O-C-O angle of 127.7-129.9 degrees, dependent on the substitute groups of N-heterocyclic ring. The length of the C-carboxylate-C-NHO bond is in the range of 1.55-1.57 angstrom, significantly longer than that of the C-carboxylate-C-NHC bond (1.52-1.53 angstrom) of the previously reported NHC-CO2 adducts. The FTIR study by monitoring the v(CO2) region of transmittance change demonstrated that the decarboxylation of NHO-CO2 adducts is easier than that of the corresponding NHC-CO2 adducts. Notably, the NHO-CO2 adducts were found to be highly active in catalyzing the carboxylative cyclization of CO2 and propargylic alcohols at mild conditions (even at ambient temperature and 0.1 MPa CO2 pressure), selectively giving alpha-alkylidene cyclic carbonates in good yields. The catalytic activity is about 10-200 times that of the corresponding NHC-CO2 adducts at the same conditions. Two reaction paths regarding the hydrogen at the alkenyl position of cyclic carbonates coming from substrate (path A) or both substrate and catalyst (path B) were proposed on the basis of deuterium labeling experiments. The high activity of NHO-CO2 adduct was tentatively ascribed to its low stability for easily releasing the CO2 moiety and/or the desired product, a possible rate-limiting step in the catalytic cycle.

  DOI：

  10.1021/ja405114e
• 作为产物：
  描述：

  1,2-二甲基咪唑 、 2-碘代丙烷 以 乙腈 为溶剂， 以77%的产率得到1-isopropyl-2,3-dimethylimidazolium iodide
  参考文献：
  名称：

  含咪唑鎓离子液体的大体积基团的便捷合成

  摘要：

  我们报告了基于咪唑鎓的离子液体的庞大基团的合成。使用方便的方法将庞大的基团引入咪唑环的N-1，C-2和N-3位置。J.杂环化​​学。（2012）。

  DOI：

  10.1002/jhet.751

文献信息

• IMIDAZOLIUM CATIONS WITH EXCEPTIONAL ALKALINE STABILITY
  申请人：Cornell University

  公开号：EP4108691A1

  公开（公告）日：2022-12-28

  The invention provides a compound of formula (II): wherein: R1 is wherein ∗ represents the point of attachment to the nitrogen atom at position 1 of the imidazolium ring; m is 0 or 1; n is 1-8, provided that the sum of m + n does not exceed 8; R2 is phenyl substituted with 0 to 3 substituents R6 individually selected from C1-C3 alkyl; R3 is selected from C2-C16 hydrocarbyl; R4 and R5 are individually selected from C1-C16 hydrocarbyl, or taken together R4 and R5, together with the carbon atoms to which they are attached, form a ring selected from benzene, cyclooctene and norbornene; and X- is a counterion.

  本发明提供了一种式 (II) 的化合物： 其中 R1 是 其中 ∗ 代表与咪唑环位置 1 的氮原子的连接点； m 为 0 或 1； n 为 1-8，但 m+n 之和不超过 8； R2 是被 0 至 3 个单独选自 C1-C3 烷基的取代基 R6 取代的苯基； R3 选自 C2-C16 烃基； R4 和 R5 单独选自 C1-C16 碳氢基，或 R4 和 R5 与它们所连接的碳原子一起形成一个选自苯、环辛烯和降冰片烯的 环；以及 X- 是反离子。
• Imidazoles and imidazolium cations with exceptional alkaline stability
  申请人：CORNELL UNIVERSITY

  公开号：US11242432B2

  公开（公告）日：2022-02-08

  The invention provides: imidazole and imidazolium compounds of formulas (I) and (II): polymers containing a plurality of imidazolium-containing repeating units of formula (III′): and membranes and devices comprising the polymers. Also provided are methods of making the inventive compounds and polymers.

  本发明提供：式 (I) 和 (II) 的咪唑和咪唑鎓化合物： 含有多个式（III′）含咪唑重复单元的聚合物： 以及包含这些聚合物的膜和装置。此外，还提供了制造本发明化合物和聚合物的方法。
• Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships
  作者：Kristina M. Hugar、Henry A. Kostalik、Geoffrey W. Coates

  DOI：10.1021/jacs.5b02879

  日期：2015.7.15

  Highly base-stable cationic moieties are a critical component of anion exchange membranes (AEMs) in alkaline fuel cells (AFCs); however, the commonly employed organic cations have limited alkaline stability. To address this problem, we synthesized and characterized the stability of a series of imidazolium cations in 1, 2, or 5 M KOH/CD3OH at 80 degrees C, systematically evaluating the impact of substitution on chemical stability. The substituent identity at each position of the imidazolium ring has a dramatic effect on the overall cation stability. We report imidazolium cations that have the highest alkaline stabilities reported to date, >99% cation remaining after 30 days in 5 M KOH/CD3OH at 80 degrees C.
• IMIDAZOLES AND IMIDAZOLIUM CATIONS WITH EXCEPTIONAL ALKALINE STABILITY
  申请人：Cornell University

  公开号：EP3283535A2

  公开（公告）日：2018-02-21
• [EN] IMIDAZOLES AND IMIDAZOLIUM CATIONS WITH EXCEPTIONAL ALKALINE STABILITY<br/>[FR] IMIDAZOLES ET CATIONS D'IMIDAZOLIUM PRÉSENTANT UNE STABILITÉ ALCALINE EXCEPTIONNELLE
  申请人：UNIV CORNELL

  公开号：WO2016168468A2

  公开（公告）日：2016-10-20

  The invention provides: imidazole and imidazolium compounds of formulas (I) and (II): (Formulas (I), (II)); polymers containing a plurality of imidazolium-containing repeating units of formula (III'): (Formula (III')); and membranes and devices comprising the polymers. Also provided are methods of making the inventive compounds and polymers.