(E,E)-2,6-bis[2,2,2-trifluoroethylidene]cyclohexanone | 152500-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,E)-2,6-bis[2,2,2-trifluoroethylidene]cyclohexanone
• 英文别名: 2,6-Bis(2,2,2-trifluoroethylidene)cyclohexanone；(2E,6E)-2,6-bis(2,2,2-trifluoroethylidene)cyclohexan-1-one
• CAS: 152500-07-7
• 化学式: C₁₀H₈F₆O
• 分子量: 258.163
• InChiKey: CZZNPQJCROKGCB-YDFGWWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 (E,E)-2,6-bis[2,2,2-trifluoroethylidene]cyclohexanone 以 环己烷 为溶剂， 反应 1.0h， 以26%的产率得到3,3''-bis(trifluoromethyl)dispiro[bicyclo[2.2.1]heptane-2,1'-cyclohexane-3',2''-bicyclo[2.2.1]heptane]-5,5''-dien-2'-one
  参考文献：
  名称：

  Synthetic Applications of α-Fluoroalkylated Enones. 1. Use as Dienophiles in Diels−Alder Cycloadditions

  摘要：

  beta-Fluoroalkylated enones are efficient dienophiles in Diels-Alder cycloadditions to prepare various fluorinated cylic compounds. However, the presence of the fluoroalkyl moiety modifies the reactivity and the selectivity of these cycloadditions.

  DOI：

  10.1021/jo052567+
• 作为产物：
  描述：

  2,6-bis[1-(4-benzylpiperazino)-2,2,2-trifluoroethyl]cyclohexanone 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以75%的产率得到(E,E)-2,6-bis[2,2,2-trifluoroethylidene]cyclohexanone
  参考文献：
  名称：

  Reactivity of Stable Trifluoroacetaldehyde Hemiaminals. 1. An Unexpected Reaction with Enolizable Carbonyl Compounds

  摘要：

  In the presence of enolizable carbonyl compounds, hemiaminals of fluoral and related polyfluoro-aldehydes behave as equivalents of fluoroalkyl iminium compounds and provide beta -polyfluoroalkyl beta -dialkylamino ketones, which are easily transformed, under acidic conditions, into beta -polyfluoroalkylenones.

  DOI：

  10.1021/jo015587u

文献信息

• Trifluoroethylidenation of compounds with activated methylene groups
  作者：Célal Ates、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/s0040-4039(00)73840-8

  日期：1993.9

  α-trifluoromethyl iminium trifluoroacetates 5 can be prepared from N-oxides 4 and used in situ or after isolation. Condensation occurs with carbonyl activated methylene groups to give useful β-trifluoromethyl vinyl ketones 8.

  α-三氟甲基亚胺基三氟乙酸盐5可以由N-氧化物4制备并原位使用或分离后使用。与羰基活化的亚甲基发生缩合，得到有用的β-三氟甲基乙烯基酮8。
• Synthetic Applications of α-Fluoroalkylated Enones. 1. Use as Dienophiles in Diels−Alder Cycloadditions
  作者：Julia Leuger、Gaëlle Blond、Roland Fröhlich、Thierry Billard、Günter Haufe、Bernard R. Langlois

  DOI：10.1021/jo052567+

  日期：2006.3.31

  beta-Fluoroalkylated enones are efficient dienophiles in Diels-Alder cycloadditions to prepare various fluorinated cylic compounds. However, the presence of the fluoroalkyl moiety modifies the reactivity and the selectivity of these cycloadditions.
• Reactivity of Stable Trifluoroacetaldehyde Hemiaminals. 1. An Unexpected Reaction with Enolizable Carbonyl Compounds
  作者：Gaëlle Blond、Thierry Billard、Bernard R. Langlois

  DOI：10.1021/jo015587u

  日期：2001.7.1

  In the presence of enolizable carbonyl compounds, hemiaminals of fluoral and related polyfluoro-aldehydes behave as equivalents of fluoroalkyl iminium compounds and provide beta -polyfluoroalkyl beta -dialkylamino ketones, which are easily transformed, under acidic conditions, into beta -polyfluoroalkylenones.