1-isoquinolyl trifluoromethanesulfonate | 123172-86-1

• 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: 1-isoquinolyl trifluoromethanesulfonate
• 英文别名: Isoquinolin-1-yl trifluoromethanesulfonate
• CAS: 123172-86-1
• 化学式: C₁₀H₆F₃NO₃S
• 分子量: 277.224
• InChiKey: LKRXPWBAEDPVJK-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43 °C
• 沸点：
  368.6±42.0 °C(Predicted)
• 密度：
  1.555±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-isoquinolyl trifluoromethanesulfonate 在 乙酰氯 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以90%的产率得到1-碘异喹啉
  参考文献：
  名称：

  Microwave-Assisted Trans-Halogenation Reactions of Various Chloro-, Bromo-, Trifluoromethanesulfonyloxy- and Nonafluorobutanesulfonyloxy-Substituted Quinolines, Isoquinolines, and Pyridines Leading to the Corresponding Iodinated Heterocycles

  摘要：

  Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic. anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.

  DOI：

  10.1021/jo9008386
• 作为产物：
  描述：

  三氟甲磺酸酐 、 1-羟基异喹啉 在 吡啶 作用下， 反应 16.0h， 以79%的产率得到1-isoquinolyl trifluoromethanesulfonate
  参考文献：
  名称：

  Crisp, Geoffrey T.; Papadopoulos, Spiros, Australian Journal of Chemistry, 1989, vol. 42, # 2, p. 279 - 285

  摘要：

  DOI：

文献信息

• Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides
  作者：Jiang Wu、Yafei Liu、Changhui Lu、Qilong Shen

  DOI：10.1039/c6sc00082g

  日期：——

  A palladium-catalyzed difluoromethylthiolation of heteroaryl halides and triflates under mild conditions was described. A vast range of heteroaryl halides such as pyridyl, quinolinyl, benzothiazolyl, thiophenyl, carbazolyl and pyazolyl halides could be difluoromethylthiolated efficiently, thus providing medicinal chemists with new tools for their search of new lead compounds for drug discovery. Likewise

  描述了在温和条件下钯催化的杂芳基卤化物和三氟甲磺酸二氟甲基硫醇化反应。各种杂芳基卤化物（例如吡啶基，喹啉基，苯并噻唑基，硫代苯基，咔唑基和吡唑基卤化物）可以有效地被二氟甲基硫醇化，从而为药物化学家提供了寻找新的先导化合物以发现药物的新工具。同样，在改良的反应条件下，高产率地将芳基碘化物二氟甲基硫醇化。
• A New Approach to Polycyclic Azonia Cations by Ring-Closing Metathesis
  作者：Ana Núñez、Ana M. Cuadro、Julio Alvarez-Builla、Juan J. Vaquero

  DOI：10.1021/ol070773t

  日期：2007.8.1

  metathesis (RCM) reaction of N-vinyl-alpha-(2-styryl)azinium salts, using the Hoveyda-Grubbs catalyst, leads to different tricyclic and tetracyclic azonia cations with moderate to good yields. This is the first time that a highly electron-deficient alkene such as an N-vinylpyridinium has been involved in an RCM process.

  使用Hoveyda-Grubbs催化剂的N-乙烯基-α-（2-苯乙烯基）叠氮盐的闭环复分解（RCM）反应可产生不同的三环和四环氮阳离子，且收率中等至良好。这是首次在RCM工艺中引入高度缺乏电子的烯烃（例如N-乙烯基吡啶鎓）。
• Synthesis of AzaaromaticBorane Intramolecular Complexes by Palladium-Catalyzed Reaction of Azaaromatic Halides with Alkynyl(triaryl)borates
  作者：Naoki Ishida、Mizuna Narumi、Masahiro Murakami

  DOI：10.1002/hlca.201200554

  日期：2012.12

  A diversity‐oriented method to synthesize (E)‐azastilbenes having an intramolecular BN coordination bond from alkynyl(triaryl)borates and azaaromatic halides is described. The obtained π‐conjugated compounds exhibit an intense blue fluorescence and a high electron affinity, indicating their potential to be used as n‐type light‐emitting materials.

  一个面向分集的方法来合成（É）-azastilbenes具有分子内乙从炔基（三芳基）硼酸盐和azaaromatic卤化物Ñ配位键进行说明。所获得的π共轭化合物表现出强烈的蓝色荧光和高电子亲和力，表明它们具有用作n型发光材料的潜力。
• Water-Soluble Luminescent Cyclometalated Gold(III) Complexes with<i>cis</i>-Chelating Bis(N-Heterocyclic Carbene) Ligands: Synthesis and Photophysical Properties
  作者：Faan-Fung Hung、Wai-Pong To、Jing-Jing Zhang、Chensheng Ma、Wai-Yeung Wong、Chi-Ming Che

  DOI：10.1002/chem.201403103

  日期：2014.7.7

  A new class of cyclometalated AuIII complexes containing various bidentate C‐deprotonated C^N and cis‐chelating bis(N‐heterocyclic carbene) (bis‐NHC) ligands has been synthesized and characterized. These are the first examples of AuIII complexes supported by cis‐chelating bis‐NHC ligands. [Au(C^N)(bis‐NHC)] complexes display emission in solutions under degassed condition at room temperature with emission

  合成并表征了一类新型的含各种双齿C-去质子化的C ^ N和顺式螯合双（N-杂环卡宾）（bis-NHC）配体的环金属化的Au III配合物。这些是顺式螯合双-NHC配体支持的Au III络合物的第一个实例。[金（C ^ N）（双- NHC）]在室温下，与发射最大值（脱气的条件下的解决方案的复合物显示发射λ最大）在高达10.1％的498-633 nm，发射量子产率。发射被分配给C ^ N配体的三重态配位体（IL）π→π*跃迁。金III复杂的含有C ^ N（C-去质子化的萘取代的喹啉）配位体具有扩展的π共轭展品提示荧光和强度可比的磷光具有λ最大在454和611纳米的分别。使用磺酸盐官能化的bis-NHC配体，制备了四种水溶性发光Au III配合物，包括同时显示荧光和磷光的配合物。与乙腈相比，它们在水中的光物理性质相似。具有C-去质子化萘取代的喹啉配体的水溶性AuIII配合物的磷光寿命长，使其可用作氧气的比例传感器。这些水溶性Au
• Syntheses of acetylquinolines and acetylisoquinolines via palladium-catalyzed coupling reactions
  作者：Jean-Yves Legros、Gaëlle Primault、Jean-Claude Fiaud

  DOI：10.1016/s0040-4020(01)00076-x

  日期：2001.3

  acetylisoquinolines were obtained from the corresponding chloro-, bromo- or trifluoromethylsulfonyloxy-heteroaromatics via four different palladium-catalyzed coupling reactions: (i) Stille coupling with tri(n-butyl)-1-ethoxyvinylstannane; (ii) Negishi coupling with 1-ethoxyvinylzinc chloride; (iii) cross-coupling with tri(1-ethoxyvinyl)indium; (iv) Heck arylation of n-butyl vinyl ether.

  Acetylquinolines和acetylisoquinolines从相应的氯得到的，溴-或通过四种不同的钯催化偶联反应三氟甲基磺酰氧基-杂芳族化合物：（ⅰ）的Stille与三（耦合Ñ丁基）-1- ethoxyvinylstannane; （ii）Negishi与1-乙氧基乙烯基锌氯化物偶联；（iii）与三（1-乙氧基乙烯基）铟交叉偶联；（iv）正丁基乙烯基醚的Heck芳基化。