2-氟-2,2-二硝基乙醇 | 17003-75-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-氟-2,2-二硝基乙醇
• 英文名称: 2-fluoro-2,2-dinitroethanol
• 英文别名: FDNE；2,2-dinitro-2-fluoroethanol
• CAS: 17003-75-7
• 化学式: C₂H₃FN₂O₅
• mdl: MFCD01727928
• 分子量: 154.055
• InChiKey: DKSPPEUUPARRFY-UHFFFAOYSA-N

物化性质

• 沸点：
  62-64 °C(Press: 2 Torr)
• 密度：
  1.6894 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氟-2,2-二硝基乙醇 在 sodium dichromate 、 硫酸 作用下， 生成 二硝基氟甲烷
  参考文献：
  名称：

  Direct fluorination of secondary nitronate salts

  摘要：

  DOI：

  10.1021/jo00828a077
• 作为产物：
  描述：

  2,2-二硝基乙醇 在 fluorine 作用下， 生成 2-氟-2,2-二硝基乙醇
  参考文献：
  名称：

  Dinitromethane

  摘要：

  DOI：

  10.1021/jo00412a014

文献信息

• Study on the synthesis of 2-fluoro-2,2-dinitroethyl esters as a potential melt cast matrix in explosive charges
  作者：Jinchao Ma、Hongwei Yang、Guangbin Cheng

  DOI：10.1039/c7nj02717f

  日期：——

  Polynitro energetic compounds with low melting points, high thermal stabilities, good detonation properties, and considerably mechanical insensitivities are reported; some of these compounds are promising potential replacements of TNT used in melt cast explosives.

  聚硝基能量化合物具有低熔点、高热稳定性、良好的爆轰性能和相当的机械不敏感性；其中一些化合物有望成为熔融铸造炸药中用于取代TNT的有前途的潜在替代品。
• Facile Addition of Poorly Nucleophilic Alcohols to Unactivated Alkenes
  作者：Dale F. Shellhamer

  DOI：10.1055/s-1997-1313

  日期：1997.9

  Electronegative substituted (polyfluorinated and polynitroaliphatic), poorly nucleophilic alcohols are efficiently added to model alkenes norbornene, cyclohexene, hex-1-ene, and hex-3-ene under mild conditions by the use of boron trifluoride-diethyl ether complex catalyst, forming the corresponding ethers.

  电负性取代的（含氟和含硝环烷基的）、弱亲核性的醇类在温和条件下，通过使用三氟化硼二乙醚络合物催化剂，有效地加成到模型烯烃降樟烯、环己烯、己-1-烯和己-3-烯中，形成相应的醚。
• Addition reactions of alkenes with electronegatively substituted alcohols in the presence of xenon difluoride
  作者：Melvin L. Druelinger、Dale F. Shellhamer、Robert D. Chapman、Scott A. Shackelford、Maurice E. Riner、Steven L. Carter、Ryan P. Callahan、Cameron R. Youngstrom

  DOI：10.1039/a604677k

  日期：——

  The electrophilic reactivity of proposed alkoxyxenon fluoride (ROXeF) intermediates based on electronegatively substituted (polyfluorinated and polynitroaliphatic) alcohols has been characterized with model alkenes norbornene, 2-methylpent-1-ene and hex-1-ene. The alkoxyxenon fluorides can react as positive oxygen electrophiles—initially incorporating alkoxy substituents—or as apparent fluorine electrophiles—resulting in initial fluorine incorporation—depending on conditions. Efficient simple addition of poorly nucleophilic alcohols to norbornene was observed in certain systems. Selectivity between the various reaction paths (simple fluorination, alkoxyfluorination or alcohol addition) was observed to be a sensitive function of various reaction conditions, especially solvent, temperature and catalyst.

  根据电负性取代的（多氟化和多硝基脂肪族）醇，提出的醇氧氟氙（ROXeF）中间体的电亲反应性已通过模型烯烃如内苯、2-甲基戊-1-烯和己-1-烯进行表征。这些醇氧氟氙可作为正氧电亲体反应——最初引入醇氧取代基——或作为表观氟电亲体反应——导致初始氟的引入——具体取决于反应条件。在某些体系中，观察到欠亲核醇与内苯之间的高效简单加成。不同反应路径（简单氟化、醇氧氟化或醇加成）之间的选择性被认为是各种反应条件的敏感函数，特别是溶剂、温度和催化剂。
• Trinitromethylation reactions of chloro-1,3,5-triazines
  作者：A. A. Gidaspov、V. V. Bakharev、I. K. Kukushkin

  DOI：10.1007/s11172-009-0294-x

  日期：2009.10

  Reactions of chloro-1,3,5-triazines with trinitromethane salts were studied. Depending on conditions, trinitromethane salts used and special additives, six types of 2,4,6-trichloro-1,3,5-triazine trinitromethylation reactions were revealed, namely, bis-trinitromethylation-nitro-nyloxylation, bis-trinitromethylation-amination, bis-trinitromethylation-hydroxylation, trinitromethylation-dialkoxylation, trinitromethylation-diaryloxylation, and trinitromethylation-alkoxylation-aryloxylation. The mechanisms of reactions are proposed.

  对氯代-1,3,5-三嗪与三硝基甲烷盐的反应进行了研究。根据反应条件、所用三硝基甲烷盐及特定添加剂，揭示了六种类型的2,4,6-三氯-1,3,5-三嗪三硝基甲基化反应，即：双三硝基甲基化-硝基-氮氧基化、双三硝基甲基化-氨基化、双三硝基甲基化-羟基化、三硝基甲基化-双烷氧基化、三硝基甲基化-双芳氧基化，以及三硝基甲基化-烷氧基化-芳氧基化。提出了反应机制。
• Synthesis of vinyl ethers
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US04426540A1

  公开（公告）日：1984-01-17

  Vinyl ethers are prepared by reacting divinyl ether with a primary alcohol in the presence of a catalytic amount of red mercuric oxide and trifluoroacetic acid. The vinyl ethers so produced are particularly useful as monomers which can be polymerized into energetic macromolecular binder materials with excellent mechanical, physical and energetic properties.

  乙烯醚是通过在存在少量红色氧化汞和三氟乙酸的催化剂下，将二乙烯醚与一种初级醇反应制备而成。所生产的乙烯醚特别适用作为单体，可聚合成具有优异机械、物理和能量特性的高分子粘合材料。