2,2’,3,3’,4,5,5’,6,6’-nonafuoro-4’’-methoxy-1,1’,2’,1’’-terphenyl | 1562625-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2’,3,3’,4,5,5’,6,6’-nonafuoro-4’’-methoxy-1,1’,2’,1’’-terphenyl
• 英文别名: 2,2',3,3',4,5,5',6,6'-nonafluoro-4''-methoxy-1,1':4',1''-terphenyl；1,2,3,4,5-Pentafluoro-6-[2,3,5,6-tetrafluoro-4-(4-methoxyphenyl)phenyl]benzene；1,2,3,4,5-pentafluoro-6-[2,3,5,6-tetrafluoro-4-(4-methoxyphenyl)phenyl]benzene
• CAS: 1562625-61-9
• 化学式: C₁₉H₇F₉O
• 分子量: 422.25
• InChiKey: GFVCQAVXOQKXDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  十氟联苯 、 4-甲氧基苯基溴化镁 以 四氢呋喃 为溶剂， 反应 24.0h， 以96%的产率得到2,2’,3,3’,4,5,5’,6,6’-nonafuoro-4’’-methoxy-1,1’,2’,1’’-terphenyl
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Fluorinated Arenes from Perfluorinated Arenes Coupled with Grignard Reagents

  摘要：

  A simple method to obtain organofluorine compounds from perfluorinated arenes coupled with Grignard reagents in the absence of a transition-metal catalyst was reported. In particular, the perfluorinated arenes could react not only with aryl Grignard reagents but also with alkyl Grignard reagents in moderate to good yields.

  DOI：

  10.1021/om4011609

文献信息

• Transition‐Metal‐Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles
  作者：Lucie Finck、Martin Oestreich

  DOI：10.1002/chem.202101731

  日期：2021.8.2

  coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N’-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (SNAr). These reactions typically proceed at room temperature

  报道了足够缺电子的氟化芳烃和官能化的N-芳基-N'-甲硅烷基二氮烯作为掩蔽的芳基亲核试剂的化学选择性 C(sp 2 )-C(sp 2 ) 偶联。氟化物促进的转化涉及原位生成用各种敏感官能团修饰的芳基亲核试剂，然后逐步进行亲核芳族取代 (S N Ar)。这些反应通常在室温下在几分钟内进行。这种催化过程允许两个偶联伙伴的功能化，以良好的产率提供高度氟化的联芳基化合物。
• Palladium-Catalyzed Coupling Reaction of Perfluoroarenes with Diarylzinc Compounds
  作者：Masato Ohashi、Ryohei Doi、Sensuke Ogoshi

  DOI：10.1002/chem.201303451

  日期：2014.2.10

  to promote the oxidative addition of one CF bond of C6F6 to palladium. Stoichiometric reactions revealed that an expected oxidative‐addition product, trans‐[Pd(C6F5)I(PCy3)2], generated from the reaction of [Pd(PCy3)2] with C6F6 in the presence of lithium iodide, was not involved in the catalytic cycle. Instead, a transient three‐coordinate, monophosphine‐ligated species, [Pd(C6F5)I(PCy3)], emerged

  该报告描述了六氟苯（C 6 F 6）与二芳基锌化合物的首次Pd 0催化交叉偶联，得到了多种五氟苯基芳烃。该反应可以应用于其他全氟芳烃，例如八氟甲苯，五氟吡啶和全氟萘，以得到相应的多氟偶联产物。在该催化反应中的最佳配体是PCy 3，碘化锂作为偶联反应的添加剂是必不可少的。碘化锂在该催化反应中的作用之一是促进C 6 F 6的一个CF键的氧化加成。钯。化学计量反应表明，在存在条件下，[Pd（PCy 3）2 ]与C 6 F 6的反应产生了预期的氧化加成产物反式[Pd（C 6 F 5）I（PCy 3）2 ]。碘化锂的一部分不参与催化循环。取而代之的是，瞬态三配位单膦连接的物质[Pd（C 6 F 5）I（PCy 3）]出现为催化循环中的潜在中间体。因此，我们分离了一种新型的Pd II复合物[Pd（C 6 F 5）I（PCy3）（py）]，其中吡啶（py）充当不稳定的配体以生成瞬态物质。实际上，在碘化锂的存在下，发现该Pd
• Transition-Metal-Free Synthesis of Fluorinated Arenes from Perfluorinated Arenes Coupled with Grignard Reagents
  作者：Yunqiang Sun、Hongjian Sun、Jiong Jia、Aiqin Du、Xiaoyan Li

  DOI：10.1021/om4011609

  日期：2014.2.24

  A simple method to obtain organofluorine compounds from perfluorinated arenes coupled with Grignard reagents in the absence of a transition-metal catalyst was reported. In particular, the perfluorinated arenes could react not only with aryl Grignard reagents but also with alkyl Grignard reagents in moderate to good yields.