3-重氮基-1,1,1-三氟-2,4-戊二酮 | 170752-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-重氮基-1,1,1-三氟-2,4-戊二酮
• 英文名称: 3-diazo-1,1,1-trifluoro-2,4-pentanedione
• 英文别名: 3-diazo-1,1,1-trifluoropentane-2,4-dione；(Z)-3-diazonio-1,1,1-trifluoro-4-oxopent-2-en-2-olate
• CAS: 170752-47-3
• 化学式: C₅H₃F₃N₂O₂
• 分子量: 180.086
• InChiKey: JTVFQOYGMHAWGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-重氮基-1,1,1-三氟-2,4-戊二酮 以 乙醚 为溶剂， 生成 3-methylcarbonyl-6-phenyl-4-trifluoromethylpyridazine
  参考文献：
  名称：

  由氟化重氮二酮合成4-氟烷基取代的哒嗪

  摘要：

  两种方法被报告用于从含有氟烷基diazodiketones制备的3,4,6-三取代的哒嗪：维悌希/施陶丁格/序列氮杂-Wittig和施陶丁格/维蒂希/二氮杂-Wittig反应。与通过初始磷嗪相比，在第一阶段进行维蒂希反应可提高目标哒嗪的收率。在这两种方法中，合成的最后阶段（乙烯基膦嗪的形成和随后的diaza -Wittig反应）都是串联的过程。与未氟化的酰基和芳酰基羰基相比，R F活化的羰基在重氮二羰基和1,3-二氧杂磷嗪分子的Wittig烯化反应中具有更高的反应性（R FCO≫ COAlk，COAr），因此在相同条件下，非氟化的重氮二酮及其膦嗪不会产生哒嗪。

  DOI：

  10.1016/j.jfluchem.2007.01.004
• 作为产物：
  描述：

  三氟乙酰丙酮 在 4-methyl-3-nitrobenzenesulfonyl azide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到3-重氮基-1,1,1-三氟-2,4-戊二酮
  参考文献：
  名称：

  Wittig Reaction of a Series of Diazodiketones: Synthesis and Structure of Fluorine-Containing Vinyldiazoketones

  摘要：

  (烷氧羰基)-和(苯甲酰)-甲烯三苯基膦与含氟二氮烯二酮的反应导致了全氟酰基羰基的烯化，并形成了氟化的乙烯基二氮烯二酮。与非氟化二氮烯二酮的类似反应在相同条件下不发生。所得的含氟乙烯基二氮烯二酮具有E-构型，无论取代基的性质和大小如何。

  DOI：

  10.1055/s-2005-872180

文献信息

• Synthesis of Aryldiazoacetates through Palladium(0)-Catalyzed Deacylative Cross-Coupling of Aryl Iodides with Acyldiazoacetates
  作者：Fei Ye、Chengpeng Wang、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201407653

  日期：2014.10.20

  Palladium(0)‐catalyzed deacylative cross‐coupling of aryl iodides and acyldiazocarbonyl compounds can be achieved at room temperature under mild reaction conditions. The coupling reaction represents a highly efficient and general method for the synthesis of aryldiazocarbonyl compounds, which have found wide and increasing applications as precursors for generating donor/acceptor‐substituted metallocarbenes

  钯（0）催化的芳基碘化物和酰基重氮羰基化合物的脱酰基交叉偶联可在室温下在温和的反应条件下实现。偶联反应代表了合成芳基重氮羰基化合物的一种高效且通用的方法，该方法作为生成供体/受体取代的金属碳烯的前体已得到越来越广泛的应用。
• Facile Synthesis of Fluorinated Benzofuro- and Benzothieno[2,3-b]pyridines, α-Carbolines and Nucleosides Containing the α-Carboline Framework
  作者：Viktor Iaroshenko、Yan Wang、Biao Zhang、Dmitriy Volochnyuk、Vyacheslav Sosnovskikh

  DOI：10.1055/s-0029-1217396

  日期：2009.7

  Fluorinated benzofuro[2,3-b]pyridines, benzo­thieno[2,3-b]pyridines and 9H-pyrido[2,3-b]indoles (α-carbolines) were synthesized via regiospecific pyridine core annulation of a number of fluoro-containing 1,3-CCC-dielectrophiles to benzofuran-2-amine, benzothiophen-2-amine and 1H-indol-2-amine. Based on the 2,4-bis(trifluoromethyl)-9H-pyrido[2,3-b]indole thus synthesized, the preparative approach towards a set of nucleosides and nucleoside mimetics bearing the α-carboline framework was elaborated.

  合氟苯并呋喃[2,3-b]吡啶、苯并噻吩[2,3-b]吡啶和9H-吡啶[2,3-b]吲哚（α-卡宾）通过多种含氟的1,3-CCC-双电亲体与苯并呋喃-2-胺、苯并噻吩-2-胺和1H-吲哚-2-胺进行区域选择性的吡啶核心环化反应合成。基于所合成的2,4-二（三氟甲基）-9H-吡啶[2,3-b]吲哚，进一步阐述了制备一系列具有α-卡宾结构的核苷和核苷类似物的方法。
• Fluorinated Diazo Diketones in Rhodium(II)-Catalyzed Reactions with Sultams: ChemoselectiveO-Functionalization of Amide Carbonyl Groups
  作者：Valeria M. Zakharova、Bärbel Schulze、Ludmila L. Rodina、Joachim Sieler、Valerij A. Nikolaev

  DOI：10.1002/hlca.200590146

  日期：2005.7

  diketones in the presence of isothiazole-3(2H)-one 1,1-dioxides offers a chemoselective and useful tool for O-functionalization of their CO groups by interaction with transient fluorine-containing RhII-diketocarbenoids. The resulting O-alkylimidates of isothiazole 1,1-dioxides, bearing (trifluoromethyl)acetyl groups, easily react with traces of H2O giving rise to stable hydrates of the perfluoroacetyl

  在异噻唑-3（2 H）-1存在下，铑（II）催化的氟化重氮二酮的分解为1,1-二氧化物提供了一种化学选择性和有用的工具，可通过与瞬态含氟化合物相互作用来对其CO基进行O-官能化Rh II-二酮类化合物。所得的带有（三氟甲基）乙酰基的异噻唑1，1-二氧化物的O-烷基亚氨酸酯容易与痕量的H 2 O反应，产生稳定的全氟乙酰基水合物。没有ø Ñ的异构化ø -alkylimidates（类似于兰德-查普曼重排）研究了反应条件下进行了观察。
• Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study
  作者：G. Prakash、Valerij Nikolaev、Murat Supurgibekov

  DOI：10.1055/s-0032-1318309

  日期：——

  Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and trans-vinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF3, OTBS) at the C-3 atom of the vinyl double bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonyl compounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16-37%. An approach via diazo transfer followed by the Wittig reaction, in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37-69%). The configuration of the resulting F-and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.
• Stereochemical aspect of the intramolecular diaza-wittig reaction
  作者：M. B. Supurgibekov、L. Hennig、B. Schulze、V. A. Nikolaev

  DOI：10.1134/s1070428008120221

  日期：2008.12