1,3-dinitro-5-(2,2,2-trifluoroethoxy)benzene | 208333-78-2

• 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: 1,3-dinitro-5-(2,2,2-trifluoroethoxy)benzene
• 英文别名: 1-(2,2,2-trifluoroethoxy)-3,5-dinitrobenzene
• CAS: 208333-78-2
• 化学式: C₈H₅F₃N₂O₅
• 分子量: 266.133
• InChiKey: DNLKNSZHTPDRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-dinitro-5-(2,2,2-trifluoroethoxy)benzene 在 氢氧化钾 、 硫酸 、 硝酸 、 sodium methylate 作用下， 以 异丙醇 为溶剂， 生成 3-amino-7-nitro-5-(2,2,2-trifluoroethoxy)-1,2,4-benzotriazine 1-oxide
  参考文献：
  名称：

  Synthesis of 5-alkoxy-3-amino-7-nitro-1,2,4-benzotriazine 1-oxides from 1,3,5-trinitrobenzene

  摘要：

  1-Alkoxy-3,5-dinitrobenzenes were nitrated to give 1-alkoxy-2,3,5-trinitrobenzenes. The reaction of the latter with guanidine affords N-(2-alkoxy-4,6-dinitrophenyl)guanidines, which undergo cyclization under the action of KOH to form 5-alkoxy-3-amino-7-nitro-1,2,4-benzotriazine 1-oxides.

  DOI：

  10.1007/bf02495174
• 作为产物：
  描述：

  1,3,5-三硝基苯 、 2,2,2-三氟乙醇 在 N-甲基吡咯烷酮 、 potassium carbonate 作用下， 以81%的产率得到1,3-dinitro-5-(2,2,2-trifluoroethoxy)benzene
  参考文献：
  名称：

  Reaction of polyfluorinated alcohols with 1,3,5-trinitrobenzene and its analogs

  摘要：

  DOI：

  10.1007/bf02495630

文献信息

• Dual reactivity of 1-chloro- and 1-bromo-3,5-dinitrobenzenes in aromatic nucleophilic substitution
  作者：Mikhail D. Dutov、Svyatoslav A. Shevelev、Vladimir N. Koshelev、David R. Aleksanyan、Olga V. Serushkina、Olga D. Neverova、Evgeniya V. Kolvina、Egor S. Bobrov

  DOI：10.1016/j.mencom.2017.03.018

  日期：2017.3

  Aromatic nucleophilic substitution reactions in 1-halo-3,5-dinitrobenzenes (where the halogen is bromine or chlorine) can occur with replacement of either a nitro group or a halogen atom, depending on the nature of anionic nucleophile Nu– as a Lewis base (hard, soft or intermediate), as well as on the polarity of the dipolar aprotic solvent.

  根据阴离子亲核试剂Nu–作为路易斯碱的性质，在1-卤代3,5-二硝基苯（卤素为溴或氯）中发生芳香亲核取代反应，同时取代硝基或卤素原子（硬，软或中间）以及偶极非质子溶剂的极性。
• Direct Amination of 1-Substituted 3,5-Dinitrobenzenes by 1,1,1-Trimethylhydrazinium Iodide
  作者：Vladimir V. Rozhkov、Svyatoslav A. Shevelev、Ivan I. Chervin、Alexander R. Mitchell、Robert D. Schmidt

  DOI：10.1021/jo005774c

  日期：2003.3.1

  The amination of 1-X-3,5-dinitrobenzenes via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK or NaOMe in DMSO was studied. It was observed (when X = OMe, OCH2CF3, OCH2CF2CF2H, OPh) that the amination occurs regioselectively (ratio of ortho/pares-isomers is similar to9:1) and with high yield. For X = SPh or SCH2Ph, the reaction proceeded with a low yield (less than 20%), with a ratio of ortho/pares-isomers approximate to 1:1. For X = PhSO2 and 2 equiv of TMHI, a double amination occurs and 2,4-diamino-3,5dinitro-1-phenylsulfonylbenzene predominates in the mixture of isomers. Under the same conditions, 1,3,5-trinitrobenzene undergoes a double amination to yield 2,4diamino-1,3,5-trinitrobenzene. A proposed mechanism for this reaction is discussed.
• ——
  作者：E. G. Nikiforova、M. A. Korolev、I. V. Shakhkel'dyan、M. D. Dutov、Yu. D. Grudtsyn、Yu. M. Atroshchenko、S. A. Shevelev、V. A. Subbotin

  DOI：10.1023/a:1012416322310

  日期：——

  A number of 7-polyfluoroalkoxy-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes were synthesized by reduction of 3,5-dinitrophenyl polyfluoroalkyl ethers with sodium tetrahydridoborate, followed by the Mannich reaction with formaldehyde and primary amines.
• Reaction of polyfluorinated alcohols with 1,3,5-trinitrobenzene and its analogs
  作者：S. A. Shevelev、M. D. Dutov、M. A. Korolev、O. Yu. Sapozhnikov、A. L. Rusanov

  DOI：10.1007/bf02495630

  日期：1998.8
• Synthesis of 5-alkoxy-3-amino-7-nitro-1,2,4-benzotriazine 1-oxides from 1,3,5-trinitrobenzene
  作者：V. V. Rozhkov、S. A. Shevelev

  DOI：10.1007/bf02495174

  日期：2000.9

  1-Alkoxy-3,5-dinitrobenzenes were nitrated to give 1-alkoxy-2,3,5-trinitrobenzenes. The reaction of the latter with guanidine affords N-(2-alkoxy-4,6-dinitrophenyl)guanidines, which undergo cyclization under the action of KOH to form 5-alkoxy-3-amino-7-nitro-1,2,4-benzotriazine 1-oxides.