二氟(3,3,3-三氟丙-1-炔基)硼烷 | 663152-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 二氟(3,3,3-三氟丙-1-炔基)硼烷
• 英文名称: perfluoroprop-1-ynyldifluoroborane
• 英文别名: trifluoropropynyldifluoroborane；Difluoro(3,3,3-trifluoroprop-1-yn-1-yl)borane；difluoro(3,3,3-trifluoroprop-1-ynyl)borane
• CAS: 663152-72-5
• 化学式: C₃BF₅
• 分子量: 141.836
• InChiKey: SMRWIMHYLAZPJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二氟(3,3,3-三氟丙-1-炔基)硼烷 在 三氟化硼 作用下， 以 1,1,1,3,3-五氟丙烷 为溶剂， 反应 1.0h， 以31%的产率得到bis(trifluoroprop-1-yn-1-yl)bromonium tetrafluoroborate
  参考文献：
  名称：

  双（全氟有机基）溴鎓盐[（R F）2 Br] Y（R F  =芳基，烯基和炔基）

  摘要：

  溴鎓盐[（R ˚F）2溴- ] Y与全氟化基团- [R ˚F Ç 6 ˚F 5，CF 3 CF CF，C 2 ˚F 5 CF CF，和CF 3 C≡C，从BRF的反应分离出3，其中R ˚F BF 2在弱配位溶剂（wcs）中，例如CF 3 CH 2 CHF 2（PFP）或CF 3 CH 2 CF 2 CH 3（PFB），收率30-90％。C 6 F 5高炉2仅仅与化学计量无关地形成[[C 6 F 5）2 Br] [BF 4 ]。BrF 3与硅烷C 6 F 5 SiY 3（Y = F，Me）的1：2反应以不同的产物– C 6 F 5 BrF 2或[（C 6 F 5）2 Br] [SiF 5 ] –终止纯的个体，取决于Y和反应温度（Y = F）。在≥−30°C时使用C 6 F 5 SiF 3 [[C 6 F 5）2 Br] [SiF5 ]导致产率为92％，而具有较少路易斯酸性C 6 F 5 SiMe

  DOI：

  10.1016/j.jfluchem.2010.06.006
• 作为产物：
  描述：

  potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate 在 三氟化硼 作用下， 以 various solvent(s) 为溶剂， 反应 0.17h， 以93%的产率得到二氟(3,3,3-三氟丙-1-炔基)硼烷
  参考文献：
  名称：

  A well feasible and general route to (organoethynyl)difluoroboranes, RHCCBF2, and their perfluorinated analogues, RFCCBF2

  摘要：

  A representative series of (organoethynyl)difluoroboranes RC equivalent to CBF2 (R=C4H9, (CH3)(3)C, CF3, C3F7, (CF3)(2)CF, CF3CF=CF, C4F9CF=CF, C6F5) was prepared by abstraction of fluoride from the corresponding K[RC equivalent to CBF3] salts with BF3 in appropriate solvents' (1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluorobutane, or dichloromethane). (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.12.012

文献信息

• Organoethynylxenon(II) Tetrafluoroborates, [RC≡CXe][BF ₄ ] – The First Examples of Isolated Alkynylxenonium Salts: Preparation and Multi‐NMR Characterisation
  作者：Hermann‐Josef Frohn、Vadim V. Bardin

  DOI：10.1002/ejic.200600366

  日期：2006.10

  perfluorinated organoethynylxenon(II) salts, [RC≡CXe][BF4] [R = CF3, C3F7, (CF3)2CF, cis-, trans-CF3CF=CF, C6F5], were prepared by the reaction of XeF2 with the corresponding perfluoroorganoethynyldifluoroboranes, RC≡CBF2, in 1,1,1,3,3-pentafluoropropane (PFP) or CH2Cl2 at –60 to –40 °C and isolated in 30–98 % yield. Similarly, the non-fluorinated organoethynylxenon(II) salts [C4H9C≡CXe][BF4] and [(CH3)3CC≡CXe][BF4]

  全氟化有机乙炔基氙 (II) 盐 [RC≡CXe][BF4] [R = CF3, C3F7, ( )2CF, cis-, trans- CF=CF, C6F5]，通过 XeF2 与相应的反应制备全氟有机乙炔基二氟硼烷，RC≡CBF2，在 –60 至 –40 °C 的 1,1,1,3,3-五氟丙烷 (PFP​​) 或 CH2Cl2 中，并以 30–98% 的产率分离。类似地，非氟化有机乙炔基氙(II)盐[ C≡CXe][BF4]和[(CH3)3CC≡CXe][BF4]的产率为20%至40%。所有 [RC≡CXe][BF4] 盐都可溶于无水 HF (aHF)，并且 R = C4H9 或 R = ( )3C 的盐在弱配位溶剂 和 PFP 中显示出足够的溶解度。鎓盐[RC≡CXe][BF4]通过它们在溶液中的1H-、11B-、13C-、19F-和129Xe NMR光谱进行了明确表征。(©
• Trifluoropropynylxenon(<scp>ii</scp>) tetrafluoroborate [CF₃CCXe] [BF₄] – isolation of an alkynylxenon(<scp>ii</scp>) compound for the first time
  作者：Hermann-Josef Frohn、Vadim V. Bardin

  DOI：10.1039/b307583d

  日期：——

  The salt [CF3CCXe] [BF4] was prepared as neat compound by the reaction of the hitherto unknown alkynyldifluoroborane CF3CCBF2 with XeF2 in 1,1,1,3,3-pentafluoropropane (PFP) at −45 °C in 59% yield. [CF3CCXe] [BF4] was unambiguously characterised by multinuclear NMR spectroscopy in anhydrous HF (aHF) solution.

  通过将迄今未知的炔基二氟硼烷 CF3CCBF2 与 XeF2 在 1,1,1,3,3- 五氟丙烷 (PFP) 中于 â45 °C 进行反应，制备出了纯化合物 [CF3CCXe] [BF4]，收率为 59%。[CF3CCXe][BF4]在无水 HF (aHF) 溶液中通过多核核磁共振光谱得到了明确的表征。
• New types of asymmetrical bromonium salts [RF(RF′)Br]Y where RF and/or RF′ represent perfluorinated aryl, alkenyl, and alkynyl groups
  作者：Hermann-Josef Frohn、Matthias Giesen、Vadim V. Bardin

  DOI：10.1016/j.jfluchem.2010.06.022

  日期：2010.10

  A series of previously unknown asymmetrical fluorinated bis(aryl)bromonium, alkenyl(aryl)bromonium, and alkynyl(aryl)bromonium salts was prepared by reactions of C6F5BrF2 or 4-CF3C6H4BrF2 with aryl group transfer reagents Ar'SiF3 (Ar' = C6F5, 4-FC6H4, C6H5) or perfluoroorganyl group transfer reagents R-F'BF2 (R-F = C6F5, trans-CF3CF=CF, C3F7C C) preferentially in weakly coordinating solvents (CCl3F, CCl2FCClF2, CH2Cl2, CF3CH2CHF2(PFP), CF3CH2CF2CH3 (PFB)). The presence of the base MeCN and the influence of the adducts R-F'BF2 center dot NCMe (R-F = C6F5, CF3C C) on reactions aside to bromonium salt formation are discussed. Reactions of C6F5BrF2 with Alk(F)'BF2 in PFP gave mainly C6F5Br and Alk(F)'F (Alk(F)' = C6F13, C6F13CH2CH2), presumably, deriving from the unstable salts [C6F5(Alk(F)')Br]Y (Y = [Alk(F)'BF3](-)). Prototypical reactivities of selected bromonium salts were investigated with the nucleophile I- and the electrophile H+. [4-CF3C6H4(C6F5)Br][BF4] showed the conversion into 4-CF3C6H4Br and C6F5I when reacted with [Bu4N]I in MeCN. Perfluoroalkynylbromonium salts [CnF2n+1C C(R-F)Br][BF4] slowly added HF when dissolved in aHF and formed [Z-CnF2n+1CF=CH(R-F)Br][BF4]. (C) 2010 Elsevier B.V. All rights reserved.