2-methyl-4,5,6,7-tetrafluoroisoindole | 38053-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-methyl-4,5,6,7-tetrafluoroisoindole
• 英文别名: 4,5,6,7-tetrafluoro-2-methylisoindole；N-methyl-4,5,6,7-tetrafluoroisoindole；4,5,6,7-Tetrafluoro-2-methyl-2H-isoindole
• CAS: 38053-09-7
• 化学式: C₉H₅F₄N
• 分子量: 203.139
• InChiKey: GZGZEBKOUQJSOT-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177.5 °C
• 沸点：
  249.2±35.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-4,5,6,7-tetrafluoroisoindole 在 sodium hydroxide 、 苄基三乙基氯化铵 、 苯基锂 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 生成 1,2,3,4-tetrafluoro-7,10-dioctyltetracene
  参考文献：
  名称：

  Syntheses of Soluble, π-Stacking Tetracene Derivatives

  摘要：

  The syntheses of a series of fluorine- and alkyl/alkoxy-functionalized tetracenes are reported. These functional groups are found to improve the solubility in common organic solvents and tune molecular arrangement in solids. The crystal packing, electrochemical behavior, and UV-vis absorbance spectroscopy of these materials are discussed.

  DOI：

  10.1021/ol0526468
• 作为产物：
  描述：

  氯五氟苯 在 正丁基锂 、 3,6-二-2-吡啶基-1,2,4,5-四嗪 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 生成 2-methyl-4,5,6,7-tetrafluoroisoindole
  参考文献：
  名称：

  Synthesis and properties of novel fluorinated subnaphthalocyanines for organic photovoltaic cells

  摘要：

  Novel fluorinated subnaphthalocyanine derivatives were newly designed and synthesized as donor materials for low molecular organic photovoltaic cells using fullerene as an acceptor. They were designed to have the low-lying HOMO energy levels for improvement of open circuit voltage without any expense of short-circuit current density. The HOMO/LUMO energy levels of hexafluoro-, heptafluoro-, dodecafluoro-, tridecafluoro- and the parent subnaphthalocyanine estimated based on the photoelectron spectroscopy were -5.69/-3.93, -5.67/-3.90, -5.96/-4.19, -5.92/-4.11 and -5.30/-3.58 eV, respectively, showing that frontier orbital energy levels can be effectively tuned by fluorination. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.069

文献信息

• Structure Elucidation of 2D Polymer Monolayers Based on Crystallization Estimates Derived from Tip-Enhanced Raman Spectroscopy (TERS) Polymerization Conversion Data
  作者：Wei Wang、Feng Shao、Martin Kröger、Renato Zenobi、A. Dieter Schlüter

  DOI：10.1021/jacs.9b01765

  日期：2019.6.26

  Structural elucidation of 2D polymer monolayers proving long-range order is a challenge that limits the pace in which this recent field of polymer chemistry and of synthetic 2D materials develops. To overcome this bottleneck, we here present a method in which tip-enhanced Raman spectroscopy is combined with a random growth crystallization model to obtain global features from local spectroscopic information

  证明长程有序的二维聚合物单层的结构阐明是一项挑战，它限制了聚合物化学和合成二维材料这一最新领域的发展步伐。为了克服这个瓶颈，我们在这里提出了一种方法，将尖端增强拉曼光谱与随机生长结晶模型相结合，从局部光谱信息中获取全局特征。具体来说，我们证明了两种新的 2D 均聚物和一种（三种）新的 2D 共聚物的性质并确定了交联的转化数 X。假设随机和面内生长，我们的模型导致 93.1% 至 99.7% 的结晶度和 3-15 nm 的无缺陷结晶区域的平均半径，转换数为 84% < X < 98%。因此，我们为合成单层 2D 材料提供了强有力的证据，证明它们符合 2D 聚合物的条件，因此非常适合在更基本的方向和应用方面进行深入研究。这个例子展示了我们的方法如何影响当前对共价片的研究。
• Preparation and spectroscopic studies of the 1,4-dihydro- 1,4-iminonaphthalene (7-azabenzonorbornadiene) ring system
  作者：John W. Davies、Michael L. Durrant、Matthew P. Walker、Djaballah Belkacemi、John R. Malpass

  DOI：10.1016/s0040-4020(01)88190-4

  日期：——

  (7-azabenzonorbornadienes) and reduced derivatives is described together with 1,4-dihydro-1,4- and 9,10-dihydro-9,10- iminoanthracenes. VT NMR studies lead to unambiguous assignment of invertomer preferences; changes in the invertomer ratios and nitrogen inversion barriers are investigated as the electronic and steric environment is modified by variation of substituents in the carbon skeleton and at nitrogen

  描述了一系列N-烷基1,4-二氢-1,4-亚氨基萘（7-氮杂苯并降冰片二烯）和还原衍生物与1,4-二氢-1,4-和9,10-二氢-9的合成，10-亚氨基蒽。VT NMR研究可明确确定内向异构体的偏好。随着碳骨架中和氮原子上取代基的变化而改变了电子和空间环境，研究了转化体比率和氮转化障碍的变化。
• Synthesis and Nonlinear Optical Properties of Fluorine-Containing Naphthalocyanines
  作者：Guo Ying Yang、Michael Hanack、Yiew Wang Lee、Yu Chen、May Ka Yuen Lee、Danilo Dini

  DOI：10.1002/chem.200204683

  日期：2003.6.16

  The fluorine-containing metal naphthalocyanines [F16NcGaCl] (7) and [(F16NcGa)2O] (8), which represent the first examples of peripherally fluorine substituted naphthalocyanines, were synthesized, and the nonlinear optical transmission was studied. Peripheral substitution by fluorine atoms enhances the solubility and photostability of the naphthalocyanines. In particular, for the axially mu-oxo-bridged

  合成了代表周边被氟取代的萘菁的第一实例的含氟金属萘菁[F16NcGaCl]（7）和[（F16NcGa）2O]（8），并研究了非线性光学透射率。氟原子的周边取代增强了萘酞菁的溶解度和光稳定性。特别是，对于轴向多氧桥联萘酞菁二聚体8，在有机溶剂中几乎没有观察到聚集，并且当用波长为532 nm的激光脉冲照射时，它是有效的光学限制剂，脉冲持续时间为5 ns和20 Hz的重复频率。
• Novel ‘windscreen wiper’ cavity structures formed by the cycloaddition of N-substituted isoindoles onto molrac bis-alkenes
  作者：John R Malpass、Guangxing Sun、John Fawcett、Ronald N Warrener

  DOI：10.1016/s0040-4039(98)00364-5

  日期：1998.5

  strong N-substituent effect is observed in the reaction of isoindoles with cyclobutene-1,2-diesters: N-alkyloxycarbonyl derivatives react to form adducts with bent-frame stereostructures; N-alkylisoindoles produce both extended-frame (stable) and bent-frame (unstable) stereoisomers, but require high-pressure conditions (10–15 kbar); N-acyl isoindoles fail to react. Reaction of N-benzyl tetrafluoroisoindole

  在异吲哚与环丁烯-1，2-二酯的反应中观察到强烈的N-取代作用：N-烷氧羰基衍生物反应形成具有弯曲骨架立体结构的加合物；N-烷基异吲哚既能产生扩展骨架（稳定）又能弯曲骨架（不稳定）立体异构体，但需要高压条件（10-15 kbar）。N-酰基异吲哚不能反应。的反应Ñ苄tetrafluoroisoindole 6c中与双-烯烃13所产生的第一个“挡风玻璃刮水器” Ñ -bridged腔化合物12，其结构是由X射线分析确认。
• Stereoselective diels-alder reactions between 9-alkyl-1,4-dihydronaphthalen-1,4-imines and 2-alkylisoindoles
  作者：Gordon W. Gribble、Craig S. LeHoullier

  DOI：10.1016/0040-4039(81)89004-1

  日期：1981.1

  The Diels-Alder reaction between 9-alkyl-1,4-dihydronaphthalen-1,4-imines () and 2-alkylisoindoles () occurs in refluxing xylene to give exclusively the exo-endo cyclo-adducts ().

  9-烷基-1,4-二氢萘-1,4-亚胺（）和2-烷基异吲哚（）之间的Diels-Alder反应发生在回流的二甲苯中，仅得到外-内-环加合物（）。