1-硝基-3-(3,3,3-三氟丙-1-炔基)苯 | 111727-06-1

• 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: 1-硝基-3-(3,3,3-三氟丙-1-炔基)苯
• 英文名称: 1-(3-nitrophenyl)-3,3,3-trifluoropropyne
• 英文别名: 1-nitro-3-(3,3,3-trifluoroprop1-yn-1-yl)benzene；1-nitro-3-(3,3,3-trifluoroprop-1-ynyl)benzene；1-Nitro-3-(3,3,3-trifluoroprop-1-YN-1-YL)benzene
• CAS: 111727-06-1
• 化学式: C₉H₄F₃NO₂
• 分子量: 215.131
• InChiKey: RVNSRMMWULUNLW-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 5 Torr)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-硝基苯乙炔	3-nitrophenylacetylene	3034-94-4	C8H5NO2	147.133
  ——	trimethyl((3-nitrophenyl)ethynyl)silane	183322-33-0	C11H13NO2Si	219.315

反应信息

• 作为反应物：
  描述：

  1-硝基-3-(3,3,3-三氟丙-1-炔基)苯 在 氯[2-(二叔丁基磷)二苯基]金 、 水 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以90%的产率得到3,3,3-trifluoro-1-(3-nitrophenyl)propan-1-one
  参考文献：
  名称：

  Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

  摘要：

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

  DOI：

  10.1021/acs.orglett.9b01379
• 作为产物：
  描述：

  trimethyl((3-nitrophenyl)ethynyl)silane 在 copper(l) iodide 、 四甲基乙二胺 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 1-硝基-3-(3,3,3-三氟丙-1-炔基)苯
  参考文献：
  名称：

  Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

  摘要：

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

  DOI：

  10.1021/acs.orglett.9b01379

文献信息

• Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me₃SiCF₃
  作者：Lingling Chu、Feng-Ling Qing

  DOI：10.1021/ja102175w

  日期：2010.6.2

  An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me(3)SiCF(3)) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO(2)Et, -Br, and -NO(2) were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful

  开发了一种有效的铜介导的末端炔烃与亲核三氟甲基化试剂 (Me(3)SiCF(3)) 的三氟甲基化。芳香族炔烃和脂肪族炔烃都是有效的，并且在反应条件下可以容忍各种官能团，例如氨基、-OMe、-CO(2)Et、-Br 和-NO(2)。该反应为制备三氟甲基化乙炔提供了一种通用、直接且实用的方法。
• Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkynes and Aryl Boronic Acids Using (Trifluoromethyl)trimethylsilane
  作者：Xueliang Jiang、Lingling Chu、Feng-Ling Qing

  DOI：10.1021/jo202566h

  日期：2012.2.3

  copper-mediated oxidative trifluomethylation of terminal alkynes and aryl boronic acids. This method allows a wide range of functional group tolerant trifluoromethylated acetylenes and arenes to be easily prepared. After the preliminary mechanistic studies of the oxidative trifluoromethylation of terminal alkyne, an efficient copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic

  三氟甲基化的乙炔和芳烃可广泛用于药物和农用化学品的合成。在2010年，我们小组报告了末端炔烃和芳基硼酸的铜介导的氧化三氟甲基化。该方法允许容易地制备宽范围的耐官能团的三氟甲基化的乙炔和芳烃。在对末端炔烃的氧化三氟甲基化进行了初步的机理研究之后，已经开发了有效的铜催化的末端炔烃和芳基硼酸的氧化三氟甲基化。通过使用注射泵将底物和一部分CF 3 TMS缓慢加入反应混合物中，成功实现了催化方案。
• Preparation of 1-Aryl- or 1-Alkenyl-2-(perfluoroalkyl)acetylenes
  作者：Norihiko Yoneda、Shigeru Matsuoka、Norio Miyaura、Tsuyoshi Fukuhara、Akira Suzuki

  DOI：10.1246/bcsj.63.2124

  日期：1990.7

  1-Aryl- or 1-alkenyl-2-(perfluoroalkyl)acetylenes were produced in high yields by the coupling reaction of aryl or alkenyl iodides with (perfluoroalkynyl)zinc compounds prepared from the corresponding (perfluoroalkyl)acetylenes in the presence of Pd catalyst.

  1-芳基-或1-烯基-2-(全氟烷基)乙炔通过芳基或烯基碘化物与(全氟炔基)锌化合物在Pd催化剂存在下由相应的(全氟烷基)乙炔制备的偶联反应以高产率制备。
• Aryl trifluoromethyl acetylenes
  作者：J.E. Bunch、C.L. Bumgardner

  DOI：10.1016/s0022-1139(00)82073-4

  日期：1987.8

  A wide variety of aryl trifluoromethyl acetylenes may be prepared in high yield by allowing CF3CCZnCl, generated from CF3CCH, to react with aryl iodides a catalytic amount of tetrakis(triphenylphosphine)-palladium.

  各种各样的芳基三氟甲基乙炔可以以高收率通过允许CF制备3 CCZnCl，从CF生成3 CCH，与芳基碘反应四（三苯膦）钯的催化量。
• Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives
  作者：Tsutomu Konno、Jungha Chae、Masashi Kanda、Go Nagai、Kazushige Tamura、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1016/s0040-4020(03)01199-2

  日期：2003.9

  Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2 equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2.TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh3)(4), reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields. (C) 2003 Elsevier Ltd. All rights reserved.