1-硝基-4-(2,2,2-三氟乙基)苯 | 3764-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-硝基-4-(2,2,2-三氟乙基)苯
• 英文名称: 1-nitro-4-(2,2,2-trifluoroethyl)benzene
• CAS: 3764-36-1
• 化学式: C₈H₆F₃NO₂
• 分子量: 205.136
• InChiKey: TWBBLUSIUSNNAH-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  228.4±40.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  1-硝基-4-(2,2,2-三氟乙基)苯 在 palladium on activated charcoal 溴 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 21.25h， 生成 6-(2,2,2-Trifluoro-ethyl)-benzothiazol-2-ylamine
  参考文献：
  名称：

  Riluzole Series. Synthesis and in Vivo “Antiglutamate” Activity of 6-Substituted-2-benzothiazolamines and 3-Substituted-2-imino-benzothiazolines

  摘要：

  Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2-benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo "antiglutamate" activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a beta-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2-methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazlines (61 and 64, ED50 = 10 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.

  DOI：

  10.1021/jm980202u
• 作为产物：
  描述：

  对硝基苯乙酸 在 sulfur tetrafluoride 作用下， 反应 72.0h， 以90%的产率得到1-硝基-4-(2,2,2-三氟乙基)苯
  参考文献：
  名称：

  A Facile Synthesis of Isomeric C-(2,2,2-Trifluoroethyl)anilines

  摘要：

  Three isomers of C-(2,2,2-trifluoroethyl) aniline were prepared on a multigram scale from readily available nitrophenylacetic acids in two steps. First, the carboxy groups of the latter were converted into the trifluoromethyl moieties by treatment with sulfur tetrafluoride. The obtained 2,2,2-trifluoroethyl-substituted nitrobenzenes were reduced catalytically into the corresponding anilines.

  DOI：

  10.1055/s-0031-1290295

文献信息

• Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2‐Trifluoroethyl)arenes
  作者：Zhensheng Zhao、Kevin C. Y. Ma、Claude Y. Legault、Graham K. Murphy

  DOI：10.1002/chem.201902818

  日期：——

  hydrazones of arylaldehydes with Togni's CF3 -benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this

  在氢氧化钾和氟化铯的存在下，芳基醛的azo与Togni的CF3-苯并恶唑酮试剂反应，会引发脱氮加氢三氟甲基化反应，从而生成（2,2,2-三氟乙基）芳烃。这种新颖的反应可耐受许多电子多样性的官能团和取代方式，以及萘基和杂芳基衍生的底物。该方法的优点包括容易大规模获得speed前体，速度和操作简便性，并且不含过渡金属。
• Dehydroxylative Trifluoromethylthiolation, Trifluoromethylation, and Difluoromethylation of Alcohols
  作者：Wei Zhang、Jin‐Hong Lin、Wenfeng Wu、Yu‐Cai Cao、Ji‐Chang Xiao

  DOI：10.1002/cjoc.201900364

  日期：2020.2

  functionalities for drug development. Despite significant accomplishments in the trifluoromethylthiolation, trifluoromethylation and difluoromethylation reactions, directly converting common functional groups into CF3S, CF3 or HCF2 groups is still highly desirable. Described here is the dehydroxylative trifluoromethylthiolation, trifluoromethylation and difluoromethylation of alcohols promoted by a R3P/ICH2CH2I

  CF 3 S，CF 3和HCF 2基团已被确定为药物开发的有价值的功能。尽管在三氟甲基硫醇化，三氟甲基化和二氟甲基化反应方面取得了重大成就，仍然非常需要将常见的官能团直接转化为CF 3 S，CF 3或HCF 2基团。在此描述的是由R 3 P / ICH 2 CH 2 I体系促进的醇的脱羟基三氟甲基硫醇化，三氟甲基化和二氟甲基化。所有这些脱羟基反应都是在温和条件下通过R活化羟基而实现的3 P / ICH 2 CH 2 I系统。观察到较宽的底物范围和良好的官能团耐受性。
• Metal-Free Construction of the C(sp³)–CF₃ Bond: Trifluoromethylation of Hydrazones with Togni’s Reagent under Mild Conditions
  作者：Huiying Zeng、Zhen Luo、Xinlong Han、Chao-Jun Li

  DOI：10.1021/acs.orglett.9b02072

  日期：2019.8.2

  A metal-free trifluoromethylation of hydrazones with Togni’s reagent under mild conditions was developed. Various functional groups including ester, methoxy, dimethoxy, nitro, halogen, and heterocyclic compounds were tolerated. This simple and green strategy provides a practical tool to construct C(sp3)–CF3 bonds.

  开发了在温和条件下用Togni试剂对进行的无金属三氟甲基化反应。容许各种官能团，包括酯，甲氧基，二甲氧基，硝基，卤素和杂环化合物。这种简单而绿色的策略提供了构建C（sp 3）–CF 3键的实用工具。
• Three-Component Reactions of α-CF₃ Carbonyls, NaN₃, and Amines for the Synthesis of <i>NH</i>-1,2,3-Triazoles
  作者：Leiyang Lv、Ge Gao、Yani Luo、Kuantao Mao、Zhiping Li

  DOI：10.1021/acs.joc.1c02288

  日期：2021.12.3

  important molecules including carbohydrates, nucleosides, and peptides and exhibits broad substrate scopes. We further demonstrate that the NH-1,2,3-triazoles can be smoothly converted to the regiospecific N-2 alkylated 1,2,3-triazole products. Mechanistic studies based on experiments and density functional theory calculations showed that this transformation proceeds via defluorination-initiated programmed

  由于该基序在各个科学领域的广泛应用，1,2,3-三唑组装方法的开发是一个重要课题。在这项工作中，我们证明了α-CF 3羰基、NaN 3和胺的三组分组装是为了在过渡金属下选择性构建各种 5-氨基NH -1,2,3-三唑。 - 免费和露天条件。该方法为功能化生物重要分子（包括碳水化合物、核苷和肽）提供了一种通用且操作简单的途径，并具有广泛的底物范围。我们进一步证明了NH -1,2,3-三唑可以顺利地转化为区域特异性N-2 烷基化 1,2,3-三唑产物。基于实验和密度泛函理论计算的机理研究表明，这种转变通过脱氟引发的程序取代/环化/H-转移进行，得到 4,5-双官能化的NH -1,2,3-三唑产物。
• Trifluoromethylation of haloarenes with a new trifluoro-methylating reagent Cu(O₂CCF₂SO₂F)₂
  作者：Gang Zhao、Hao Wu、Zhiwei Xiao、Qing-Yun Chen、Chao Liu

  DOI：10.1039/c6ra09011g

  日期：——

  A new trifluoromethylating reagent Cu(O2CCF2SO2F)2, which easily decomposes to generate active CuCF3 species in DMF at room temperature, has been conveniently prepared from inexpensive starting materials on scale. This new...

  新型三氟甲基化试剂Cu（O2CCF2SO2F）2易于在室温下分解，在DMF中生成活性CuCF3，已由廉价的起始原料大规模制备。这个新的...