3-[(2-三氟甲基)苯基]-1-丙烯 | 62826-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[(2-三氟甲基)苯基]-1-丙烯
• 英文名称: 1-allyl-2-(trifluoromethyl)benzene
• 英文别名: 3-[(2-Trifluoromethyl)phenyl]-1-propene；1-prop-2-enyl-2-(trifluoromethyl)benzene
• CAS: 62826-30-6
• 化学式: C₁₀H₉F₃
• 分子量: 186.177
• InChiKey: ZRIGNZQCLVRNQH-UHFFFAOYSA-N

物化性质

• 沸点：
  166.0±35.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  3-[(2-三氟甲基)苯基]-1-丙烯 在 甲基磺酰胺 、 AD-mix β 、 对甲苯磺酸 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 反应 24.0h， 生成 3-(2-(4-(2-(trifluoromethyl)benzyl)-1,3-dioxolan-2-yl)phenyl)pyrimidine
  参考文献：
  名称：

  Palladium-Catalyzed meta-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

  摘要：

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

  DOI：

  10.1021/acs.orglett.9b00433
• 作为产物：
  描述：

  2-(三氟甲基)苯硼酸 、 3-溴丙烯 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 3-[(2-三氟甲基)苯基]-1-丙烯
  参考文献：
  名称：

  Palladium-Catalyzed meta-C–H Olefination of Arene-Tethered Diols Directed by Well-Designed Pyrimidine-Based Group

  摘要：

  The palladium-catalyzed meta-olefination of arene-tethered diols attached to a well-designed pyrimidine moiety is presented. Applications of the protocol are illustrated by the synthesis of various diol-based natural products, such as coumarins, phenylpropanoids, stilbenes, and chalcones. Advantages of this method are demonstrated through the easy removal of the template and a gram-scale olefination reaction. Finally, experimental verification, including H-1 NMR, ESI-MS and IR, and DFT studies are undertaken to elucidate the mechanistic complexity.

  DOI：

  10.1021/acs.orglett.9b00433

文献信息

• Catalytic Semireduction of Internal Alkynes with All-Metal Aromatic Complexes
  作者：Pierre-Alexandre Deyris、Tatiana Cañeque、Yanlan Wang、Pascal Retailleau、Franca Bigi、Raimondo Maggi、Giovanni Maestri、Max Malacria

  DOI：10.1002/cctc.201500729

  日期：2015.10

  A simple catalytic method involving all‐metal aromatic frameworks as precatalysts ensures an efficient route to (Z)‐alkenes. Aromatic triangular palladium clusters were used to reduce internal alkynes without any trace of the formation of alkane side products. These trinuclear complexes provide a catalytic system that parallels the activity and selectivity of their best mononuclear peers, and the catalyst

  一种简单的催化方法，其中包含全金属芳族骨架作为预催化剂，可确保获得通往（Z）烯烃的有效途径。芳族三角钯簇被用于还原内部炔烃，而没有任何痕量的烷烃副产物形成。这些三核配合物提供了一种催化系统，可与它们最好的单核对等体的活性和选择性相提并论，并且该催化剂可能通过互补机制起作用。
• Functionalized Arylzinc Compounds in Ethereal Solvent:  Direct Synthesis from Aryl Iodides and Zinc Powder and Application to Pd-Catalyzed Reaction with Allylic Halides
  作者：Ryo Ikegami、Akiko Koresawa、Takanori Shibata、Kentaro Takagi

  DOI：10.1021/jo026746s

  日期：2003.3.1

  Arylzinc compounds, ArZnX, were conveniently prepared in high yields by the reaction of zinc powder with aryl iodides, which contain electron-withdrawing groups such as CO(2)CH(3), CN, Br, or CF(3) at the ortho-, meta- or para-position, or electron-donating groups such as CH(3), OCH(3), or H, at 70 degrees C in THF, at 100 degrees C, or at 130 degrees C in diglyme, respectively. Pd(dba)(2) exhibited

  通过锌粉与芳基碘化物的反应可方便地以高收率制备芳基锌化合物ArZnX，芳基碘化物在邻位含有吸电子基团，例如CO（2）CH（3），CN，Br或CF（3） -在70摄氏度的THF，100摄氏度或130摄氏度的二甘醇二甲醚中的间位或对位或电子给体基团，例如CH（3），OCH（3）或H 。Pd（dba）（2）对这些ArZnX醚溶液与烯丙基卤化物的交叉偶联显示出优异的高效催化作用，从而以高收率提供了多种官能化的烯丙基苯。反应大部分在0mol％，5mol％催化剂存在下进行5-30min。通过两个反应将芳基碘化物转化为烯丙基苯可以在一个罐中完成。
• Copper-Mediated Trifluoromethylation–Allylation of Arynes
  作者：Xinkan Yang、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.8b00101

  日期：2018.2.16

  An unprecedented three-component copper-mediated vicinal trifluoromethylation–allylation of arynes is described. A wide range of structurally diverse trifluoromethylated allylarenes can be quickly assembled in one step. The application of the method has been demonstrated in the expedient synthesis of the CF3-containing analogue of the antispasmodic drug papaverine. The new reactivity of the [CuCF3]

  描述了史无前例的三组分铜介导的邻位三氟甲基化-芳烃的烯丙基化。一步就可以快速组装多种结构多样的三氟甲基化烯丙基芳烃。该方法的应用已在合成抗痉挛药物罂粟碱的含CF 3的类似物中得到证明。由廉价的工业副产物氟仿生成的[CuCF 3 ]试剂具有新的优势，具有独特的优势。
• Catalytic Intermolecular Allylic C—H Alkylation
  作者：Andrew J. Young、M. Christina White

  DOI：10.1021/ja806867p

  日期：2008.10.29

  The first electrophilic Pd(II)-catalyzed allylic C H alkylation is reported, providing a novel method for formation of sp3-sp3 C C bonds directly from C H bonds. A wide range of aromatic and heteroaromatic linear (E)-alpha-nitro-arylpentenoates are obtained as single olefin isomers in excellent yields directly from terminal olefin substrates and methyl nitroacetate. The use of DMSO as a pi-acidic ligand

  报道了第一个亲电 Pd(II) 催化的烯丙基 CH 烷基化，为直接从 CH 键形成 sp3-sp3 CC 键提供了一种新方法。可以直接从末端烯烃底物和硝基乙酸甲酯以优异的收率获得作为单一烯烃异构体的各种芳族和杂芳族线性 (E)-α-硝基-芳基戊烯酸酯。发现使用 DMSO 作为 pi-酸性配体对于促进 pi-烯丙基钯中间体的功能化至关重要。该反应的产物是有价值的合成中间体，通过选择性还原和光学富集的 α,α-二取代氨基酸前体通过不对称共轭加成很容易转化为氨基酯。
• A Transition-Metal-Free Synthesis of Fluorinated Naphthols
  作者：Jeffrey M. Hammann、Teresa A. Unzner、Thomas Magauer

  DOI：10.1002/chem.201402098

  日期：2014.5.26

  electrocyclization, followed by rearomatization. This concept enables the rapid conversion (three steps) of various commercially available 3‐(trifluoromethyl)phenols into novel fluorine‐containing naphthols, which are difficult to prepare by previous methods. The reported sequence was also extended to a one‐pot transformation of 3‐(trifluoromethyl)phenols into 5‐fluoronaphthalen‐1‐ols.

  在此，我们描述了一种无过渡金属的方案，用于将简单的2-烯丙基3-（三氟甲基）苯酚转化为取代的5-氟萘-1-醇。该反应的关键事件包括的两个C选择性激活 F键和形成中的中间己三烯系统，其经历一个6πelectrocyclization，接着rearomatization。这一概念使各种市售的3-（三氟甲基）苯酚能够快速转化（三步）成新型的含氟萘酚，而这是以前的方法难以制备的。报告的序列还扩展为将3-（三氟甲基）苯酚一锅转化为5-氟萘-1-醇。