2-methylisoquinolin-2-ium trifluoromethanesulfonate | 124401-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-methylisoquinolin-2-ium trifluoromethanesulfonate
• 英文别名: isoqinolinium triflate；N-methylisoquinolinium triflate
• CAS: 124401-76-9
• 化学式: CF₃O₃S*C₁₀H₁₀N
• 分子量: 293.267
• InChiKey: VOWQAWXFIHTBSK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.08
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methylisoquinolin-2-ium trifluoromethanesulfonate 在 potassium carbonate 、 亚磷酸二甲酯 作用下， 以 甲基叔丁基醚 为溶剂， 反应 16.0h， 以84%的产率得到2-甲基异喹啉-1(2H)-酮
  参考文献：
  名称：

  有机催化剂结合的α-氨基烷基自由基中间体，用于控制亚胺离子的好氧氧化†

  摘要：

  研发了一种由催化剂与催化剂结合的亚胺基α-氨基烷基自由基中间体，以控制其形成和与好氧的反应性。通过容易形成自由基中间体及其随后的反应性证明了催化剂的影响，包括使用手性亚磷酸酯催化剂进行的第一催化剂控制的对映选择性好氧氧化反应。

  DOI：

  10.1039/c8ob01032c
• 作为产物：
  描述：

  异喹啉 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 以80%的产率得到2-methylisoquinolin-2-ium trifluoromethanesulfonate
  参考文献：
  名称：

  有机催化剂结合的α-氨基烷基自由基中间体，用于控制亚胺离子的好氧氧化†

  摘要：

  研发了一种由催化剂与催化剂结合的亚胺基α-氨基烷基自由基中间体，以控制其形成和与好氧的反应性。通过容易形成自由基中间体及其随后的反应性证明了催化剂的影响，包括使用手性亚磷酸酯催化剂进行的第一催化剂控制的对映选择性好氧氧化反应。

  DOI：

  10.1039/c8ob01032c

文献信息

• Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations
  作者：Jiří Šturala、Soňa Boháčová、Josef Chudoba、Radka Metelková、Radek Cibulka

  DOI：10.1021/jo502865f

  日期：2015.3.6

  prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability

  制备了一系列的单取代的嘧啶鎓和吡嗪鎓三氟甲磺酸酯和3,5-二取代的吡啶鎓三氟甲磺酸酯，并使用硫氧化作为模型反应，对过氧化氢的简单氧化催化剂进行了测试。它们的催化效率在很大程度上取决于取代基的类型，并且对于具有吸电子基团的衍生物而言是显着的，其反应性与黄酮盐相当，后者是氧合作用的主要有机催化剂。由于它们的高稳定性和良好的可及性，4-（三氟甲基）嘧啶鎓和3,5-二硝基吡啶鎓三氟甲磺酸盐是选择的催化剂，并显示出催化脂肪族和芳香族硫化物氧化为亚砜的作用，定量转化率高，制备产率高，并且具有优异的性能。化学选择性。K R +值（p K R + <5）和较小的负还原电位（E red > -0.5 V）。在催化氧化过程中原位形成的过氧化氢加合物充当底物氧化剂。通过在B3LYP / 6-311 ++ g（d，p）水平上的计算获得的从这些杂环氢过氧化物到硫代苯甲醚的转移的吉布斯自由能表明，它们是比烷基氢过氧化
• Concurrent one- and two-electron processes in electrophile/nucleophile interactions of organometallic ion pairs
  作者：R. E. Lehmann、T. M. Bockman、J. K. Kochi

  DOI：10.1021/ja00157a076

  日期：1990.1

  Interaction electrophyle/nucleophile entre CpMo(CO) 3 − et (η 5 -L)Fe(CO) 3 + , L=cyclohexadienyl, cycloheptadienyl, pentadienyl, hexadienyl

  亲电体/亲核体相互作用 entre CpMo(CO) 3 − et (η 5 -L)Fe(CO) 3 + , L=环己二烯基、环庚二烯基、戊二烯基、己二烯基
• Addition of Alcohols onto Electron-Deficient Heteroarenium Salts: A Reversible Covalent Bonding Process under Basic Conditions
  作者：Baoli Chen、En Li、Jiean Chen、Yong Huang、Feifei Song、Nicolas Guimond

  DOI：10.1055/a-2005-5372

  日期：——

  addition of benzyl alcohol onto heteroarenium salts under basic conditions was studied. Fine-tuning of the nature of the arenium and substituents allowed the discovery of a range of pyrimidinium substrates that can undergo C6-selective alcohol addition. Crossover experiments were also performed to confirm the addition-elimination equilibrium under basic conditions.

  研究了在碱性条件下苯甲醇与杂芳基盐的可逆加成反应。通过微调芳基和取代基的性质，可以发现一系列可以进行 C6 选择性醇加成的嘧啶底物。还进行了交叉实验以确认碱性条件下的加消平衡。
• Stepwise assembly of charge-transfer complexes within zeolite supercages as visual probes for shape selectivity
  作者：K. B. Yoon、J. K. Kochi

  DOI：10.1021/j100162a063

  日期：1991.5

  The shape-selective formation of various aromatic charge-transfer complexes occurs within zeolite supercages doped with methylviologen (MV2+) and other large mono- and dipyridinium acceptors. For example, ion exchange leads to a series of acceptor-doped zeolite Y such as MV(x)Y, typically with x = 1 and 2 MV2+ per supercage. Mere exposure of a hexane slurry of the colorless MVY to various substituted benzenes, naphthalenes, and anthracenes leads immediately to brilliant, distinctively colored yellow, orange, and purple zeolites, while the supernatant solution remains singularly colorless. The diffuse reflectance spectra of the colored zeolites show characteristic charge-transfer bands that are the same as those obtained in solution with MV2+ and the corresponding arene. Thus, the successful isolation of the bright orange, single crystal of a naphthalene complex with MV2+ allows X-ray crystallography to establish the relevant cofacial donor-acceptor arrangement within the zeolite cavity. Steric restrictions of the supercage are indicated in these zeolite experiments by the size and shape of the arene donors-all the methylbenzenes including pentamethylbenzene rapidly forming brilliant yellow zeolites, the single striking exception being hexamethylbenzene. Shape selectivity is also indicated by the exclusion of 1,4-dimethoxynaphthalene (but not the 2,6-isomer) as well as 9-phenyl- and 9,10-dimethylanthracene (but not 9-methylanthracene). A van der Waals "width" of roughly 8 angstrom is sufficient to inhibit an arene from complex formation, and it represents the maximum value for the kinetic diameter sigma of arenes in zeolite Y catalysis. Mass transport through zeolite Y is quantitatively evaluated by measuring the solvent effect on the rates of intercalation and extraction of various arene substrates.
• Nucleophilic addition versus electron transfer in carbonylmetallate salts. Donor-acceptor interactions in the precursor ion pairs
  作者：T. Michael Bockman、Jay K. Kochi

  DOI：10.1002/(sici)1099-1395(199707)10:7<542::aid-poc918>3.0.co;2-o

  日期：1997.7