Gingras' reagent

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Gingras' reagent
• 英文别名: tetra-n-butylammonium difluorotriphenylstannate；(n-Bu4N)(Ph3SnF2)；tetrabutylammonium triphenyldifluorostannate；[Ph3SnF2][NBu4]；tetrabutylammonium difluorotriphenylstannate；Tetrabutylazanium;triphenylstannanylium;difluoride；tetrabutylazanium;triphenylstannanylium;difluoride
• 化学式: C₁₆H₃₆N*C₁₈H₁₅F₂Sn
• 分子量: 630.492
• InChiKey: ODMXVCNGZGLSRS-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 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：

  Gingras' reagent 在 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 以99%的产率得到二苯二硫醚
  参考文献：
  名称：

  高价硅和锡化合物对亲电硫的反应性

  摘要：

  尝试使用几种亲电子硫试剂将硅和锡的高价络合物进行硫化，以在几乎中性的条件下形成碳硫键。我们提供了各种高价盐之间反应性的定性量表。开发了涉及无味元素硫的简单实用方法。它避免了在高碱性条件下使用H 2 S或含硫的标准有机锂和格氏溶液。

  DOI：

  10.1016/s0040-4039(00)00890-x
• 作为产物：
  描述：

  四丁基氟化铵 、 三苯基氟化锡 以 二氯甲烷 、 水 为溶剂， 生成 Gingras' reagent
  参考文献：
  名称：

  Observation of inter- and intramolecular CH⋯F hydrogen bonding in Gingras' salt: [n-Bu4N]+[Ph3SnF2]−

  摘要：

  The crystal and molecular structure of Gingras' salt [n-Bu4N](+) [Ph3SnF2] is reported. which reveals a variety of inter- and intramolecular C-H... F hydrogen bonding interactions, A Sn-119 MAS-NMR spectrum was recorded and a tensor analysis has been performed according to the method of Herzfeld and Berger. The results are discussed in terms of the molecular structure and are compared with the parent compound Ph3SnF as well as with Mes(3)SnF (Mes = mesityl). (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01419-x
• 作为试剂：
  描述：

  2-甲基-1-丁烯-3-酮 、 三甲基硅基苯甲酮 、 (三氟甲基)三甲基硅烷 在 四氯化钛 、 Gingras' reagent 作用下， 生成 2,2-difluoro-4-methyl-1-phenylhexane-1,5-dione
  参考文献：
  名称：

  Mixed organofluorine-organosilicon chemistry. 8. One-pot synthesis of 2,2-difluoro-1,5 diketones from acylsilanes, trifluoromethyltrimethylsilane and enones, and their annulation reaction

  摘要：

  We describe the synthesis of 2,2-difluoro-1,5-diketones in a one-pot procedure from an acylsilane and trifluoromethyltrimethylsilane, via reaction of difluoroenoxysilanes and enones under electrophilic activation. These diketones are interesting building blocks for the synthesis of gem-difluoro enones or substituted fluorophenols, depending on the annulation conditions. The annulation proceeds with complete regioselectivity controlled by the fluorine substitution. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00224-5

文献信息

• Triazolo-pyridazine derivatives as ligands for GABA receptors
  申请人：Merck Sharp & Dohme Limited

  公开号：US06579875B1

  公开（公告）日：2003-06-17

  1,2,4-triazolo[4,3-b]pyridazine derivatives, possessing a fluoro-substituted phenyl ring at the 3-position and a heteroaryl-alkoxy moiety at the 6-position, are selective ligands for GABAA receptors, in particular having high affinity for the &agr;2 and/or &agr;3 subunit thereof, are useful in the treatment of anxiety and convulsions.

  在1,2,4-三唑并［4,3-b］吡嗪衍生物中，其在3位具有含氟取代的苯环，而在6位具有杂环烷氧基官能团，是选择性GABAA受体配体，特别是具有高亲和力的α2和/或α3亚基，对于治疗焦虑和抽搐非常有用。
• Utilization of Redox and Acid/Base Chemistry for the Deprotection of a Mn(dmpe)₂(C⋮CSiMe₃)₂ Complex
  作者：Francisco J. Fernández、Montserrat Alfonso、Helmut W. Schmalle、Heinz Berke

  DOI：10.1021/om010172k

  日期：2001.7.1

  The reaction of the low-spin d5 complex Mn(dmpe)2(C⋮CSiMe3)2 (1) (dmpe = 1,2-bis(dimethylphosphino)ethane) with [NBu4][Ph3F2M] (M = Si or Sn) yields the SiMe3 metathesis products Mn(dmpe)2(C⋮CMPh3)2 (M = Si 2a, Sn 2b). When the Mn(II) species 1 was dissolved in MeOH in the presence of NaBF4, disproportionation occurred with formation of the Mn(I) products Mn(dmpe)2(C⋮CSiMe3)(CCH2) (3a) and [Mn(dmp

  低旋转d 5复合物Mn（dmpe）2（C⋮CSiMe 3）2（1）（dmpe = 1,2-双（二甲基膦基）乙烷）与[NBu 4 ] [Ph 3 F 2 M]的反应（M ＝ Si或Sn）产生SiMe 3复分解产物Mn（dmpe）2（C ＝ CMPh 3）2（M ＝ Si 2a，Sn 2b）。当在NaBF 4存在下将Mn（II）物质1溶解在MeOH中时，歧化发生，形成Mn（I）产物Mn（dmpe）2（C⋮CSiMe3）（C CH 2）（3a）和[Mn（dmpe）2（C⋮CSiMe 3）（⋮C-CH 3）] [BF 4 ]（5a）和阳离子Mn（III）络合物[Mn（dmpe） ）2（C⋮CSiMe 3）2 ] [BF 6 ]（4a）。以类似的方式将1转化为[Mn（dmpe）2（C⋮CSiMe 3）2 ] [H 2 F 3 ]（4b）和[Mn（dmpe）2（C⋮CSiMe 3）（⋮C-CH 3）]
• Low Temperature Multinuclear NMR Study of the Mechanism of Protonation of W(H)2Cl2(PMe2Ph)4
  作者：Helmut Rothfuss、Dmitry G. Gusev、Kenneth G. Caulton

  DOI：10.1021/ic00115a017

  日期：1995.5

  Protonation (CF3SO3H) of WH(2)Cl(2)L(4) (L = PMe(2)Ph) below -70 degrees C in CD2Cl2 gives A as the kinetic product. This shows two hydride signals at -85 degrees C, and inequivalent (A(2)M(2)) P-31 nuclei. By -70 degrees C, the kinetic product converts completely to the thermodynamic product W-VI(H)(3)Cl(2)L(4)(+), B, which has fluxional hydrides but inequivalent (A(2)M(2)) P-31 nuclei. The W-P coupling constants, the W/H T-1 value of B, and the green color of A support metal oxidation state IV for A and VI for B. By -30 degrees C, B reacts further to dissociate one phosphine, to produce stereochemically-rigid, C-3-symmetric W-VI(H)(3)Cl(2)L(3)(+), C Both the H-1 and P-31 NMR spectral patterns and the W-P coupling constant support the claimed oxidation state of W(VI) in C. Above 10 degrees C, C decomposes both in solution (CH2Cl2 or toluene) and also as a pure solid to a variety of uncharacterized products. Comparison to the result of protonation of W(H)(2)XYL(4) (XY = Br-2, I-2, CII, ClBr) support certain structural proposals for A-C and indicate how the diminished X-->W pi-donation by the heavier halides influences these oxidative and phosphine dissociation processes.
• A CONVENIENT ONE-POT SYNTHESIS OF STANNYLSILANES
  作者：Reinhard Hummeltenberg、Klaus Jurkschat、Frank Uhlig

  DOI：10.1080/10426509708044214

  日期：1997.4.1

  Stannylsilanes were synthesized in high yields by reaction of organotinchlorides with organofluorosilanes and magnesium. The fluorosilanes were prepared in good yields and under mild conditions by reaction of the corresponding chlorosilanes with [n-Bu4N][Ph3SnF2]. All products were characterized by Si-29, Sn-119 NMR spectroscopy and elemental analysis.
• Reactivity of hypervalent silicon and tin compounds toward electrophilic sulfur
  作者：Sébastien Kerverdo、Xavier Fernandez、Sophie Poulain、Marc Gingras

  DOI：10.1016/s0040-4039(00)00890-x

  日期：2000.7

  Sulfuration of hypervalent complexes of silicon and tin was attempted with several electrophilic sulfur reagents for making carbonsulfur bonds under almost neutral conditions. We provided a qualitative scale of reactivity between various hypervalent salts. Simple and practical methodologies involving non-odorous elemental sulfur were developed. It avoided the use of H2S or standardized organolithium

  尝试使用几种亲电子硫试剂将硅和锡的高价络合物进行硫化，以在几乎中性的条件下形成碳硫键。我们提供了各种高价盐之间反应性的定性量表。开发了涉及无味元素硫的简单实用方法。它避免了在高碱性条件下使用H 2 S或含硫的标准有机锂和格氏溶液。