(E)-1-methoxy-3-(3,3,4,4,5,5,6,6,6-nonafluorohexen-1-yl)benzene | 1374105-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-methoxy-3-(3,3,4,4,5,5,6,6,6-nonafluorohexen-1-yl)benzene
• 英文别名: (E)-1-methoxy-3-(3,3,4,4,5,5,6,6,6-nonafluorohex-1-en-1-yl)benzene
• CAS: 1374105-04-0
• 化学式: C₁₃H₉F₉O
• 分子量: 352.199
• InChiKey: BWLUPQCBKMOYFE-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1,3-bis(1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexan-1-yl)tetramethyldisiloxane 在 三氟化硼乙醚 、 四丁基氟化铵 、 palladium diacetate 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 180.0h， 生成 (E)-1-methoxy-3-(3,3,4,4,5,5,6,6,6-nonafluorohexen-1-yl)benzene
  参考文献：
  名称：

  Hiyama coupling reaction of fluorous alkenyl-fluorosilanes: Scope and mechanistic considerations

  摘要：

  Novel fluorous alkenyl-fluorosilanes (CnF2n+1CH=CHSiMe2F; n = 4, 6, 8; 5a-c) were synthetized in a three step procedure from perfluoroalkyliodides and dimethylvinylchlorosilane. They were first reacted with iodobenzene at room temperature in Hiyama coupling reaction (DMF, Pd(OAc)(2), TBAF, 72 h) to afford the appropriate omega-perfluoroalkyl-styrenes (CnF2n+1CH=CHC6H5, n = 4, 6, 8): then the reactivity of 5a with monosubstituted iodobenzenes was studied. The coupling reaction of Sa with o-substituted iodobenzenes usually failed, while that of with the m- and p-substituted ones gave fluorous styrenes [m- or p-(C4F9CH=CH)C6H4X], independently of the electronic effect of their substituent (X = Br, CF3, CH3, OCH3). These volatile products can easily be isolated by steam-distilltaion and purified further by distillation. The mechanism of the above coupling reactions was a pure Hiyama type involving fluoride-ion induced transmetallation without any Heck type contribution, since no coupling product of C6F13CH=CH2 and C6H5I was observed in blank control experiments using similar conditions (DMF, TBAF, Pd(OAc)(2), 72 h, 25 degrees C). (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.03.007

文献信息

• Fluoroalkenylation of boronic acids <i>via</i> an oxidative Heck reaction
  作者：Da Seul Lee、Eun Jin Cho

  DOI：10.1039/c9ob00332k

  日期：——

  A fluoroalkenylation of boronic acids with fluoroalkyl alkenes has been developed. The Pd-catalyzed oxidative Heck coupling reaction proceeds under an oxygen atmosphere at room temperature, in the absence of a base and/or a ligand, showing excellent practicality of the process. This simple transformation is highly stereoselective to provide only E-isomers. In addition to the general approach using

  已经开发了用氟代烷基烯烃对硼酸的氟代烯基化。Pd催化的氧化Heck偶联反应是在室温下在氧气气氛下，在没有碱和/或配体的情况下进行的，显示了该方法的极好的实用性。这种简单的转化是高度立体选择性的，仅提供E-异构体。除了将烯烃与官能化的氟代烷基试剂一起使用的一般方法外，该方法还通过将芳香族体系转移至缺电子的氟代烷基烯烃上，提供了一种有效的替代方法来生产有价值的有机氟。
• Mesoporous Graphitic Carbon Nitride Photocatalyzed Switchable Divergent Perfluoroalkylation of Terminal Alkynes
  作者：Xiaolin Shi、Tao Song、Qinglin Li、Xiuling Guo、Yong Yang

  DOI：10.1021/acs.orglett.2c03814

  日期：2022.12.2

  heterogeneous photocatalytic system for the switchable divergent perfluoroalkylation of terminal alkynes has been developed by employing mesoporous graphitic carbon nitride (mpg-CN) as a recyclable, nontoxic, and heavy-metal-free photocatalyst. Regulating the reaction solvents allowed libraries of perfluoroalkylated alkynes, alkenes, and alkenyl iodides to be synthesized in good-to-high yields. Furthermore

  通过使用介孔石墨氮化碳（mpg-CN）作为可回收、无毒、无重金属的光催化剂，开发了一种高效、环保的多相光催化体系，用于末端炔烃的可切换发散全氟烷基化。调节反应溶剂允许以良好到高的产率合成全氟烷基化炔烃、烯烃和烯基碘化物的库。此外，mpg-CN 适用于克级光合作用，并且可以很容易地回收以供连续重复使用。