1,1,1-trifluoro-3-nitrobut-2-ene | 401-66-1

• 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
• 英文名称: 1,1,1-trifluoro-3-nitrobut-2-ene
• CAS: 401-66-1
• 化学式: C₄H₄F₃NO₂
• mdl: MFCD09738674
• 分子量: 155.076
• InChiKey: LCWQUYWZQHRBAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-phenyl-cyclohexane-1,3-dione 、 1,1,1-trifluoro-3-nitrobut-2-ene 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 168.0h， 以50%的产率得到2-methyl-6-phenyl-3-(trifluoromethyl)-6,7-dihydro-1-benzofuran-4(5H)-one
  参考文献：
  名称：

  Synthesis of β-(trifluoromethyl)furans and spiro-gem-dichlorocyclopropanes from cyclic 1,3-dicarbonyl compounds and α-(trihaloethylidene)nitroethanes

  摘要：

  While 1,3-dicarbonyl compounds react with (E)-1,1,1-trifluoro-3-nitrobut-2-ene in the presence of sodium acetate to produce the target beta-(trifluoromethyl)furans, their reaction with (E)-1,1,1-trichloro-3-nitrobut-2-ene, under the same conditions, took an entirely different course and gave spiro-gem-dichlorocyclopropanes bearing a 1-nitroethyl moiety, with high diastereoselectivity and in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.129

文献信息

• A novel synthesis of γ-nitro ketones via detrifluoroacetylative Michael addition of 1-trifluoromethyl-1,3-diketones to conjugated nitroalkenes
  作者：Alexey Yu. Barkov、Vladislav Yu. Korotaev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.tetlet.2013.10.008

  日期：2013.12

  A novel synthesis of γ-nitro ketones via detrifluoroacetylative Michael addition of 1-trifluoromethyl-1,3-diketones to conjugated nitroalkenes in the presence of sodium acetate in ethanol at room temperature is developed. A series of trifluoromethylated 1,3-diones and nitroalkenes are surveyed to determine the scope of this high-yielding reaction.

  通过在乙醇中在乙酸钠存在下于室温下，通过将1-三氟甲基-1,3-二酮的三氟乙酰化迈克尔加成到共轭硝基烯烃上，开发了一种新颖的γ-硝基酮合成方法。对一系列三氟甲基化的1，3-二酮和硝基烯烃进行了研究，以确定该高产率反应的范围。
• Uncatalyzed reactions of α-(trihaloethylidene)nitroalkanes with push–pull enamines: a new type of ring–ring tautomerism in cyclobutane derivatives and the dramatic effect of the trihalomethyl group on the reaction pathway
  作者：Vladislav Yu. Korotaev、Alexey Yu. Barkov、Pavel A. Slepukhin、Mikhail I. Kodess、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.tetlet.2011.08.109

  日期：2011.11

  A new type of ring–ring isomerism, which consists of the reversible transformation of cyclobutane derivatives into substituted 1,2-oxazine N-oxides was found and studied by NMR spectroscopy and X-ray diffraction analysis. The starting materials were prepared by the stereoselective reaction of α-(trifluoroethylidene)nitroalkanes, which react with ethyl β-morpholino- and β-piperidinocrotonates at the

  发现了一种新型的环-环异构体，其由环丁烷衍生物可逆地转化为取代的1,2-恶嗪N-氧化物组成，并通过NMR光谱学和X射线衍射分析进行了研究。原料是通过α-（三氟乙叉基）硝基烷烃的立体选择反应制备的，后者在更亲核的α位置与乙基β-吗啉代和β-哌啶子丁酸酯反应，而α-（三氯乙叉基）硝基烷烃的反应则在α-（三氟乙叉基）硝基烷进行。 β-甲基基团给出相应的线性产物。
• N-Substituted α-trifluoromethyl β-nitro amines in the synthesis of fluorine-containing 1,2-diamines, amino alcohols, and β-amino acids
  作者：V. Yu. Korotaev、A. Yu. Barkov、M. I. Kodess、I. B. Kutyashev、P. A. Slepukhin、A. Ya. Zapevalov

  DOI：10.1007/s11172-009-0257-2

  日期：2009.9

  Reactions of 2-diazo-1,1,1-trifluoro-3-nitropropane or 1-trifluoromethyl-2-nitroethenes with amines and amino alcohols afforded N-mono- and N,N-disubstituted α-trifluoromethyl β-nitro amines, which were used to obtain a number of trifluoromethyl-containing 1,2-diamines, amino alcohols, and β-amino acids.

  2-重氮-1,1,1-三氟-3-硝基丙烷或1-三氟甲基-2-硝基乙烯与胺和氨基醇反应生成N-单和N,N-二取代的α-三氟甲基β-硝基胺，用于获得许多含三氟甲基的 1,2-二胺、氨基醇和 β-氨基酸。
• Synthesis of 1-hetaryl-5,6-dihydropyrrolo[2,1-a]isoquinolines from 1-hetarylmethyl-3,4-dihydroisoquinolines and 1,1,1-trifluoro-3-nitrobut-2-ene
  作者：V. Yu. Korotaev、V. Ya. Sosnovskikh、A. Yu. Barkov、P. A. Slepukhin、Yu. V. Shklyaev

  DOI：10.1007/s11172-015-0950-2

  日期：2015.4

  1-Hetarylmethyl-3,4-dihydroisoquinolines and their crown-containing derivatives reacted with 1,1,1-trifluoro-3-nitrobut-2-ene upon reflux in isobutanol or in toluene at room temperature to form 1-hetaryl-5,6-dihydropyrrolo[2,1-a]isoquinolines, including those with the benzocrown ether fragments.

  1-杂芳基甲基-3,4-二氢异喹啉及其含冠衍生物与1,1,1-三氟-3-硝基丁-2-烯在异丁醇或甲苯中室温回流反应生成1-杂芳基-5， 6-二氢吡咯并[2,1-a]异喹啉，包括带有苯并冠醚片段的那些。
• Synthesis of β-(trifluoromethyl)furans and spiro-gem-dichlorocyclopropanes from cyclic 1,3-dicarbonyl compounds and α-(trihaloethylidene)nitroethanes
  作者：Alexey Yu. Barkov、Vladislav Yu. Korotaev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.tetlet.2013.05.129

  日期：2013.8

  While 1,3-dicarbonyl compounds react with (E)-1,1,1-trifluoro-3-nitrobut-2-ene in the presence of sodium acetate to produce the target beta-(trifluoromethyl)furans, their reaction with (E)-1,1,1-trichloro-3-nitrobut-2-ene, under the same conditions, took an entirely different course and gave spiro-gem-dichlorocyclopropanes bearing a 1-nitroethyl moiety, with high diastereoselectivity and in good yields. (C) 2013 Elsevier Ltd. All rights reserved.