(E)-2-[2,2,2-trifluoroethylidene]-3,4-dihydro-1(2H)-naphthalenone | 355137-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-2-[2,2,2-trifluoroethylidene]-3,4-dihydro-1(2H)-naphthalenone
• 英文别名: (E)-2-(2,2,2-trifluoroethylidene)-3,4-dihydronaphthalen-1(2H)-one；(2E)-2-(2,2,2-trifluoroethylidene)-3,4-dihydronaphthalen-1-one
• CAS: 355137-28-9
• 化学式: C₁₂H₉F₃O
• 分子量: 226.198
• InChiKey: QWPLPUYIYOOIPG-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-[2,2,2-trifluoroethylidene]-3,4-dihydro-1(2H)-naphthalenone 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (R,R)-f-spiroPhos 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以27.1 mg的产率得到2-(2,2,2-trifluoroethyl)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Efficient Rh-Catalyzed Chemo- and Enantioselective Hydrogenation of 2-CF₃–Chromen/Thiochromen-4-ones

  摘要：

  DOI：

  10.1021/acs.joc.3c01723
• 作为产物：
  描述：

  2-[1-(4-benzylpiperazino)-2,2,2-trifluoroethyl]-3,4-dihydro-1(2H)-naphthalenone 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以81%的产率得到(E)-2-[2,2,2-trifluoroethylidene]-3,4-dihydro-1(2H)-naphthalenone
  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

• A Concise Synthesis of Trifluoromethylated Cyclohexenones: A One-Pot, Five-Step Domino Reaction
  作者：Carole Christophe、Thierry Billard、Bernard R. Langlois

  DOI：10.1002/ejoc.200500218

  日期：2005.9

  β-Trifluoromethylated aromatic enones can undergo, in one pot, a five-step domino process leading, with good yields, to 5-trifluoromethylated cyclohexenones that constitute valuable functionalized fluorinated building-blocks. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  β-三氟甲基化芳族烯酮可以在一锅中经历五步多米诺骨牌过程，以良好的产率得到 5-三氟甲基化环己烯酮，构成有价值的功能化氟化结构单元。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• 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.
• Efficient Rh-Catalyzed Chemo- and Enantioselective Hydrogenation of 2-CF₃–Chromen/Thiochromen-4-ones
  作者：Chaochao Xie、Qianling Guo、Xiaoxue Wu、Weiping Ye、Guohua Hou

  DOI：10.1021/acs.joc.3c01723

  日期：2023.11.17