2-(3,3,3-trifluoroprop-1-yn-1-yl)naphthalene | 1227931-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3,3,3-trifluoroprop-1-yn-1-yl)naphthalene
• 英文别名: 2-(3,3,3-Trifluoro-1-propynyl)naphthalene；2-(3,3,3-trifluoroprop-1-ynyl)naphthalene
• CAS: 1227931-86-3
• 化学式: C₁₃H₇F₃
• 分子量: 220.194
• InChiKey: OXFROVTWACNPTO-UHFFFAOYSA-N

物化性质

• 沸点：
  256.2±40.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,3,3-trifluoroprop-1-yn-1-yl)naphthalene 在 dioxo-molybdenum dichloride bis-dimethylformamide 、 copper diacetate 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  铜催化的氢芳基化反应及随后的降钙环化反应合成3-芳基-2-（三氟甲基）吲哚

  摘要：

  （三氟甲基）炔与（邻硝基苯基）硼酸的铜催化加氢芳基化选择性地得到带有邻硝基苯基的三取代的（三氟甲基）烯烃。经由钼催化的Cadogan环化，将所获得的氢芳基化产物高产率地转化成3-芳基-2-（三氟甲基）吲哚。类似地，由（邻-硝基苯基）（三氟甲基）炔和（对-茴香基）硼酸制备的加氢芳基化产物也经历了Cadogan环化，尽管反应时间更长，以高收率提供了所需的吲哚产物。

  DOI：

  10.1002/adsc.201700122
• 作为产物：
  描述：

  trimethyl(2-(naphthalen-2-yl)ethynyl)silane 在 四丁基氟化铵 、 联硼酸频那醇酯 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(3,3,3-trifluoroprop-1-yn-1-yl)naphthalene
  参考文献：
  名称：

  Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF₃]

  摘要：

  A domino hydroboration/trifluoromethylation (formal hydrotrifluoromethylation) of alkynes using the fluoroform-derived [CuCF3] reagent is achieved. Synthetically useful (E)-alkenyl-CF3 building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes. The ultimate source of CF3 is the inexpensive industrial waste fluoroform.

  DOI：

  10.1021/acs.joc.7b00755

文献信息

• Copper(I)-Catalyzed Interrupted Click Reaction with TMSCF₃: Synthesis of 5-Trifluoromethyl 1,2,3-Triazoles
  作者：Kelvin Pak Shing Cheung、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.7b01116

  日期：2017.6.2

  We herein describe a Cu(I)-catalyzed interrupted click reaction, using (trifluoromethyl)trimethylsilane (TMSCF3) as a nucleophilic CF3 source, to synthesize 5-trifluoromethyl 1,2,3-triazoles in one step from readily available terminal alkynes and azides. The reaction shows complete regioselectivity, broad substrate scope, and good functional group tolerability. The application of the reaction has been

  我们在本文中描述了使用（三氟甲基）三甲基硅烷（TMSCF 3）作为亲核CF 3来源的Cu（I）催化的间断点击反应，可从易于获得的末端炔烃中一步合成5-三氟甲基1,2,3-三唑和叠氮化物。该反应显示出完全的区域选择性，广泛的底物范围和良好的官能团耐受性。该反应的应用已在抗癫痫药鲁芬酰胺的三氟甲基化类似物的合成中得到证明。
• An Improved Copper-Mediated Oxidative Trifluoromethylation of Terminal Alkynes
  作者：Ke Zhang、Xiao-Long Qiu、Yangen Huang、Feng-Ling Qing

  DOI：10.1002/ejoc.201101550

  日期：2012.1

  An improved method for the efficient copper-mediated trifluoromethylation of terminal alkynes has been developed. This protocol highlights the convenient access to a variety of aryl-substituted trifluoromethylated alkynes by oxidative trifluoromethylation with two equivalents of TMSCF3 at room temperature.

  已开发出一种用于有效铜介导的末端炔烃三氟甲基化的改进方法。该协议强调了在室温下通过氧化三氟甲基化与两当量的 TMSCF3 方便地获得各种芳基取代的三氟甲基化炔烃。
• Direct Synthesis of a Trifluoromethyl Copper Reagent from Trifluoromethyl Ketones: Application to Trifluoromethylation
  作者：Hiroki Serizawa、Kohsuke Aikawa、Koichi Mikami

  DOI：10.1002/chem.201303828

  日期：2013.12.23

  fluorine: The direct synthesis of CuCF3 from a cuprate reagent and trifluoromethyl ketones, as one of the most economical and efficient trifluoromethyl sources, was accomplished. The advantages of this method are all of reagents employed are low‐cost, operation is simple, and the yield of CuCF3 is virtually quantitative (see scheme). Furthermore, three types of trifluoromethylations smoothly proceeded

  用氟经济：由铜酸盐试剂和三氟甲基酮（最经济，最有效的三氟甲基来源之一）直接合成CuCF 3。该方法的优势在于所使用的所有试剂成本低，操作简单且CuCF 3的产率实际上是定量的（请参阅方案）。此外，三种类型的三氟甲基化顺利进行以提供高产率的相应产物。
• Copper-Catalyzed Defluorinative Thioannulation of Trifluoropropynes for the Synthesis of 1,2-Dithiole-3-thiones
  作者：Feng Wei、Xiao-Qin Shen、Xiao-Hong Zhang、Xing-Guo Zhang

  DOI：10.1002/adsc.201800846

  日期：2018.10.18

  A simple and practical strategy for the preparation of 1,2‐dithiole‐3‐thiones via copper‐catalyzed defluorinative thioannulation of trifluoropropynes has been developed using elemental sulfur as the sole sulfur source. This reaction displays a wide substrate scope and high functional group tolerance to afford the corresponding S‐heterocycles in moderate to good yields and features efficient construction

  通过元素硫作为唯一的硫源，开发了一种简单实用的方法，该方法通过铜催化的三氟丙炔的脱氟硫代环化反应制备1,2-二硫代3-硫酮。该反应显示出较宽的底物范围和较高的官能团耐受性，能够以中等至良好的产率提供相应的S-杂环，并具有通过CF 3基团的CF键断裂有效构建多个CS键的特征。
• Fluoroform-Derived CuCF₃ for Trifluoromethylation of Terminal and TMS-Protected Alkynes
  作者：Lisi He、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.6b00999

  日期：2016.6.17

  An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.