2-(4,4,4-trifluorobut-1-yn-1-yl)naphthalene | 1390640-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4,4,4-trifluorobut-1-yn-1-yl)naphthalene
• 英文别名: 2-(4,4,4-trifluorobut-1-ynyl)naphthalene
• CAS: 1390640-19-3
• 化学式: C₁₄H₉F₃
• 分子量: 234.221
• InChiKey: HHTKMAQVIXYGLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-碘萘 在 三乙烯二胺 、 bis-triphenylphosphine-palladium(II) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 三乙胺 、 双(2-二苯基磷苯基)醚 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 26.42h， 生成 2-(4,4,4-trifluorobut-1-yn-1-yl)naphthalene
  参考文献：
  名称：

  Palladium-Catalyzed Trifluoroethylation of Terminal Alkynes with 1,1,1-Trifluoro-2-iodoethane

  摘要：

  An efficient C-sp-CH2CF3 bond-forming reaction via Pd-catalyzed 2,2,2-trifluoroethylation of aryl and alkyl terminal alkynes has been developed. This protocol proceeds under mild conditions using the readily available and cheap reagent CF3CH2I as the source of the CH2CF3 group. Various terminal aryl alkynes as well as alkylacetylenes can be transformed Into the corresponding trifluoroethylated products In good-to-excellent yields. The method is tolerant of carbonyl, nitro, ester, cyano, and even formyl groups.

  DOI：

  10.1021/ol400099h

文献信息

• Trifluoromethylation of Propargylic Halides and Trifluoroacetates Using (Ph₃P)₃Cu(CF₃) Reagent
  作者：Tony S. N. Zhao、Kálmán J. Szabó

  DOI：10.1021/ol3017287

  日期：2012.8.3

  A copper-mediated trifluoromethylation of propargylic halides and trifluoroacetates was performed with high allenyl or propargyl selectivity. The reaction proceeds smoothly with aliphatic and aromatic substituents bearing either electron-withdrawing or -supplying groups. Preliminary mechanistic results indicate an ionic mechanism involving nucleophilic transfer of the CF3 group from the Cu complex

  炔丙基卤和三氟乙酸酯的铜介导的三氟甲基化以高的烯基或炔丙基选择性进行。该反应与带有吸电子或供电基的脂族和芳族取代基平稳进行。初步的机械结果表明，离子机制涉及CF 3基团从Cu络合物到炔丙基底物的亲核转移。
• Copper-catalyzed nucleophilic trifluoromethylation of propargylic halides
  作者：Yoshihiro Miyake、Shin-ichi Ota、Masashi Shibata、Kazunari Nakajima、Yoshiaki Nishibayashi

  DOI：10.1039/c3cc44434a

  日期：——

  Reactions of propargylic halides with trifluoromethyltrimethylsilane in the presence of a catalytic amount of copper(I) thiophene-2-carboxylate (CuTC) have been found to give the corresponding trifluoromethylated products in good to high yields with a high selectivity.

  已经发现炔丙基卤化物与三氟甲基三甲基硅烷在催化量的噻吩-2-羧酸铜（I）存在下的反应以高选择性高收率地得到相应的三氟甲基化产物。
• Copper-Catalyzed Decarboxylative Trifluoromethylation of Propargyl Bromodifluoroacetates
  作者：Ryan Altman、Brett Ambler、Santosh Peddi

  DOI：10.1055/s-0033-1339128

  日期：——

  The development of efficient methods for accessing fluorinated functional groups is desirable. Herein, we report a two-step method that utilizes catalytic copper for the decarboxylative trifluoromethylation of propargyl bromodifluoroacetates is described. This protocol affords a mixture of propargyl trifluoromethanes and trifluoromethyl allenes.
• Cu-Catalyzed C–H Trifluoromethylation of 3-Arylprop-1-ynes for the Selective Construction of Allenic Csp²–CF₃ and Propargyl Csp³–CF₃ Bonds
  作者：Yun-Long Ji、Jia-Jia Luo、Jin-Hong Lin、Ji-Chang Xiao、Yu-Cheng Gu

  DOI：10.1021/acs.orglett.6b00120

  日期：2016.3.4

  A new method has been developed for the Cu-catalyzed C-H trifluoromethylation of 3-arylprop-1-ynes for the selective construction of allenic Csp(2)-CF3 and propargyl Csp(3)-CF3 bonds. The selective formation of allenic Csp(2)-CF3 and propargyl Csp(3)-CF3 bonds can be controlled by modifying the reaction conditions.