2-iodo-1,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate | 1236039-69-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-iodo-1,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate
• 英文别名: 2-Iodo-1,3-dimethylimidazol-1-ium;trifluoromethanesulfonate
• CAS: 1236039-69-2
• 化学式: CF₃O₃S*C₅H₈IN₂
• 分子量: 372.107
• InChiKey: JSGGGHDOCXBWJH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-iodo-1,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate 在 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Isothermal Calorimetric Titrations on Charge-Assisted Halogen Bonds: Role of Entropy, Counterions, Solvent, and Temperature

  摘要：

  We have conducted isothermal calorimetric titrations to investigate the halogen-bond strength of cationic bidentate halogen-bond donors toward halides, using bis(iodoimidazolium) compounds as probes. These data are intended to aid the rational design of halogen-bond donors as well as the development of halogen-bond-based applications in solution. In all cases examined, the entropic contribution to the overall free energy of binding was found to be very important. The binding affinities showed little dependency on the weakly coordinating counteranions of the halogen-bond donors but became slightly stronger with higher temperatures. We also found a marked influence of different solvents on the interaction strength. The highest binding constant detected in this study was 3.3 x 10(6) M-1.

  DOI：

  10.1021/ja2119207
• 作为产物：
  描述：

  2-碘-1-甲基-1H-咪唑 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 48.0h， 以76%的产率得到2-iodo-1,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate
  参考文献：
  名称：

  氢键诱导的氢键诱导的氢原子转移至C═N键

  摘要：

  制备了几种双齿二氢咪唑啉，并研究了用汉茨酯还原氢转移C═N键的催化剂。观察到喹啉和亚胺的高效反应，催化剂负载量低至2摩尔％。使用NMR研究和等温量热滴定法阐明了卤素键的存在。XB供体的结合常数也使用等温量热滴定法（ITC）进行测量。

  DOI：

  10.1021/ol501259q
• 作为试剂：
  描述：

  2-乙烯基-1H-吲哚 、 N-苄叉苯胺 在 2-iodo-1,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 以74%的产率得到4-(1H-indol-2-yl)-2-phenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  溶液相卤素键催化中的非键电子对与π电子：2-Vilinlindoles和亚胺的Povarov反应

  摘要：

  杂原子和π电子的非键电子对（n对）都是有效的卤素键（XB）受体。在固相和气相研究中，n对通常胜过π键轨道作为XB受体，而关于固溶相偏好的研究很少。在本文中，对通过C–I⋅⋅·N XB相互作用的Povarov反应和通过C–I⋅⋅⋅π XB相互作用的[4 + 2]环加成进行了评估，表明n对在XB催化中占主导地位。解决方案中的系统。XB供体催化的Povarov反应以良好的收率得到了多种吲哚基-四氢喹啉衍生物。还开发了吲哚基喹啉的合成方法。

  DOI：

  10.1002/adsc.202000494

文献信息

• Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study
  作者：Alexandra A. Sysoeva、Alexander S. Novikov、Mikhail V. Il'in、Vitalii V. Suslonov、Dmitrii S. Bolotin

  DOI：10.1039/d1ob01158h

  日期：——

  electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2 > 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive

  本报告展示了静电表面电位分布分析在评估一系列基于唑鎓的卤素键供体的相对催化活性方面的成功应用。观察到卤素原子上 σ 空穴的正静电势与模型反应活化的吉布斯自由能（即，卤素抽象和羰基活化）。实验证实了所应用方法的预测能力。还确定了基于唑鎓的卤素键供体的催化活性通常由唑鎓循环的结构决定，而杂环上的取代基对活性的影响有限。最终，这项研究强调了四种最有希望的唑鎓卤素键供体，预计它们将表现出高催化活性。
• ENAMINE COMPOUND AND USE THEREOF
  申请人：JAPAN SCIENCE AND TECHNOLOGY AGENCY

  公开号：US20200087245A1

  公开（公告）日：2020-03-19

  Provided are a donor-acceptor type compound having a novel structure and its use. An enamine compound represented by general formula (1) (in the formula: R 1 represents an electron-withdrawing group; A represents a divalent aromatic hydrocarbon group which may contain a substituent, a divalent aromatic heterocyclic group which may contain a substituent or a divalent unsaturated aliphatic hydrocarbon group which may contain a substituent; R 2 represents a hydrogen atom or a hydrocarbon group which may contain a substituent; R 3 and R 4 are the same or different from each other and represent an aromatic hydrocarbon group which may contain a substituent or an aromatic heterocyclic group which may contain a substituent, or R 3 and R 4 together form an optionally substituted bicyclic aromatic heterocyclic group containing two or more nitrogen atoms or a nitrogen atom and an oxygen atom or a sulfur atom, or a tricyclic aromatic heterocyclic group which may contain a substituent; and R 2 and A, or R 2 and R 3 may together form a cyclic structure).

  提供一种具有新颖结构的给受体型化合物及其用途。一种由通式（1）表示的恩胺化合物（在该式中：R1代表电子吸引基团；A代表可能含有取代基的二价芳香烃基团、可能含有取代基的二价芳香杂环基团或可能含有取代基的二价不饱和脂肪烃基团；R2代表氢原子或可能含有取代基的烃基团；R3和R4彼此相同或不同，代表可能含有取代基的芳香烃基团或可能含有取代基的芳香杂环基团，或R3和R4一起形成一个含有两个或更多个氮原子或一个氮原子和一个氧原子或一个硫原子的可选择取代的二环芳香杂环基团，或可能含有取代基的三环芳香杂环基团；以及R2和A，或R2和R3可能一起形成一个环状结构）。
• Balancing Activity and Stability in Halogen-Bonding Catalysis: Iodopyridinium-Catalyzed One-Pot Synthesis of 2,3-Dihydropyridinones
  作者：Yi Li、Yicen Ge、Rui Sun、Xiao Yang、Shipeng Huang、Huajian Dong、Yunyao Liu、Haodan Xue、Xiaoyan Ma、Haiyan Fu、Zeqin Chen

  DOI：10.1021/acs.joc.3c01028

  日期：2023.8.4

  as the halogen bond catalyst. The desired [4+2] cycloaddition products, bearing aryl, heteroaryl, alkyl, and alicyclic substituents, were successfully furnished in 28–99% yields. Mechanistic investigations proved that a strong halogen-bonding interaction forged between the iodopyridinium catalyst and imine intermediate was essential to dynamically masking the vulnerable C–I bond on the catalyst and accelerating

  以3-氟-2-碘-1-甲基吡啶鎓三氟甲磺酸盐为卤键催化剂，完成了2,3-二氢吡啶酮合成的一锅级联反应。成功地制备了所需的带有芳基、杂芳基、烷基和脂环族取代基的[4+2]环加成产物，产率为28-99%。机理研究证明，碘吡啶鎓催化剂和亚胺中间体之间形成的强卤素键相互作用对于动态掩盖催化剂上脆弱的C-I键并加速随后的氮杂-狄尔斯-阿尔德反应至关重要。
• ORGANIC OPTICAL MATERIAL
  申请人：Japan Science and Technology Agency

  公开号：EP3674381A1

  公开（公告）日：2020-07-01

  Provided is a novel donor-acceptor type compound which emits light even in a solid state. The present invention provides an organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein the complex is solid at ordinary temperature; and the organic optical material has a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift having a value corresponding to 5% or more of the value of a maximum absorption wavelength from the maximum absorption wavelength toward the long wavelength side.

  本发明提供了一种即使在固态下也能发光的新型供体-受体型化合物。本发明提供了一种有机光学材料，该材料包括由(1)具有(a)至少一个电子供体位点、(b)至少一个电子受体位点和(c)同一分子中至少一个共轭位点的共轭分子和(2)具有质子供体特性或电子对受体特性的化合物形成的复合物，该复合物在电子受体位点具有非共价相互作用，其中该复合物在常温下为固体；有机光学材料具有发射具有最大荧光波长的光的特性，该最大荧光波长会引起斯托克斯偏移，其值相当于最大吸收波长值的 5%或更多，从最大吸收波长向长波侧偏移。