1,1,1-三氟-3-(异丁氧基亚甲基)-2-丙酮 | 109317-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1,1-三氟-3-(异丁氧基亚甲基)-2-丙酮
• 英文名称: 1,1,1-trifluoro-3-(isobutoxymethylene)-2-propanone
• 英文别名: trans-4-Isobutoxy-1,1,1-trifluoro-3-buten-2-one；(E)-1,1,1-trifluoro-4-(2-methylpropoxy)but-3-en-2-one
• CAS: 109317-76-2
• 化学式: C₈H₁₁F₃O₂
• 分子量: 196.169
• InChiKey: IFCCXJXADBSREN-ONEGZZNKSA-N

物化性质

• 沸点：
  149.4±40.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-三氟-3-(异丁氧基亚甲基)-2-丙酮 在 氢氧化钾 、 水 作用下， 以 苯 为溶剂， 反应 7.0h， 以77%的产率得到(E)-3-Isobutoxy-acrylic acid
  参考文献：
  名称：

  A Convenient Synthetic Method for β-Alkoxy- and β-Phenoxyacrylic Acids and 3,4-Dihydro-2H-pyran-5- and 2,3-Dihydrofuran-4-carboxylic Acids

  摘要：

  反δ-²-三卤乙酰乙烯基醚 1 很容易在苯中被湿氢氧化钾水解，从而以极好的收率生成相应的酸 2。这种合成方法也可用于环乙烯基醚 3 和 5，从而以较高的产率制得 4 和 6。

  DOI：

  10.1055/s-1986-31854
• 作为产物：
  描述：

  [4,4,4-Trifluoro-1-(2-methylpropoxy)-3-oxobutyl] 2,2,2-trifluoroacetate 以 四氯化碳 为溶剂， 反应 19.2h， 生成 1,1,1-三氟-3-(异丁氧基亚甲基)-2-丙酮
  参考文献：
  名称：

  Addition-Elimination Reaction in the Trifluoroacetylation of Electron-Rich Olefins

  摘要：

  Reactions of electron-rich olefins such as vinyl ether 1 and vinyl sulfide 2 with trifluoroacetic anhydride in carbon tetrachloride at room temperature proceeded by the formation of addition products 7 and 8, respectively, which were identified as stable intermediates by H-1 NMR and IR spectra, eventually giving the, corresponding trifluoroacetylated olefins 5 and 6 as substitution products. These reactions were also observed in chloroform and dichloromethane in the absence. of base, such as pyridine. These results supported the addition-elimination mechanism. The processes of the addition and elimination were confirmed by the H-1 NMR spectrum and kinetic study which led to the following results: The addition products 7 and 8 were formed through a stepwise trans addition, and the trifluoroacetylated olefins 5 and 6 were self-catalytically formed from the addition products 7 and 8 through Ei, E2, or E1, depending on the stability of the cationic intermediates 3 and 4.

  DOI：

  10.1021/jo00116a045

文献信息

• Fluoro organics: A facile and exclusive synthesis of novel 2- or 4-trifluoromethyl(1H,5)arylodiazepines
  作者：A Chandra Sheker Reddy、P Shanthan Rao、R.V Venkataratnam

  DOI：10.1016/0040-4039(96)00402-9

  日期：1996.4

  Exclusive formation of either 2- or 4-trifluoromethyl(1H,5)arylodiazepines was observed in the condensation of 1,1,1-trifluoro-3-(isobutoxymethylene)-2-propanones (RH,COCF3) 2 with o-arylenediamines 1 under microwave irradiation conditions. Thermal reactions under the same temperature and time produced no products.

  在1,1,1-三氟-3-（异丁氧基亚甲基）-2-丙烷（RH，COCF 3）2与邻位缩合反应中观察到2-或4-三氟甲基（1H，5）芳基二氮杂的排他性形成。-芳基二胺1在微波辐射条件下。在相同温度和时间下的热反应不会产生任何产物。
• Reactions of β-alkoxyvinyl trifluoromethyl ketones with terminal alkynes — Reagent-controlled regioselectivity addition reactions
  作者：Shizheng Zhu、Guifang Jin、Huiling Jiang

  DOI：10.1139/v05-247

  日期：2005.12.1

  butyl lithium, les reactions des β-alcoxyvinyi trifluoromethyl cetones de formule generale ROCH=CHCOCF 3 (1; R = Et, Me 2 CHCH 2 ) et de leurs analogues cycliques, tels le 4-trifluoroacetyl-2,3-dihydrofurane (2a) et le 5-trifluoroacetyl-3,4-dihydro-2H-pyrane (2b) avec des alcynes vrais de formule generale R-C≡CH (3; R = Ph, PhCH 2 , HOCH 2 , C 5 H 11 ) conduisent principalement a des produits d'additions

  在脱丁基锂的存在下，从 β-alcoxyvinyi trifluoromethyl cetones deformule generale ROCH=CHCOCF 3 (1; R = Et, Me 2 CHCH 2 ) et de leurs 类似物 cycliques, tels le 4-trifluoroacetyl-2,3-dihydrofurane 的反应(2a) et le 5-trifluoroacetyl-3,4-dihydro-2H-pyrane (2b) avec des alcynes vrais deformule generale RC≡CH (3; R = Ph, PhCH 2 , HOCH 2 , C 5 H 11 ) principalement a des produits d'additions 1,2 (alcynylation du carbonyle)。Toutefois，lorsque
• Cycloaddition reactions of β-trifluoroacetylvinyl ethers
  作者：Shizheng Zhu、Guifang Jin、Weimin Peng、Qichen Huang

  DOI：10.1016/s0040-4020(03)00344-2

  日期：2003.4

  4-dihydro-2H pyrans. These products are formed by elimination and addition of the alcohol to the products of the normal hetero Diels–Alder reaction (2-alkoxyl-3-trifluoroacetyl-2,3-dihydro-2H pyrans). In contrast, 1,3-dipolar cycloaddition of ROCHCHCOCF3 with ArCHN(O)Me proceeds via a Z-endo transition state to give regio- and stereospecific 4-trifluoroacetyl substituted isoxazolidines and their derivatives

  β-三氟乙酰基乙烯基醚ROCH = CHCOCF 3作为亲二烯体与α，β-不饱和羰基化合物平稳反应，生成意外的2-烷氧基-5-三氟乙酰基-3,4-二氢-2 H吡喃。这些产物是通过消除醇并将其添加到常规杂Diels-Alder反应产物（2-烷氧基-3-三氟乙酰基-2,3-二氢-2 H吡喃）中而形成的。与此相反，ROCHCHCOCF的1,3-偶极环加成3与ArCHN（O）Me经由前进ž -内型过渡状态，得到区域选择性和立体有择的4-三氟乙酰基取代的异恶唑烷和它们的衍生物。
• A Convenient Synthesis of Fluorine-Containing Dihydrobenzo[b][1,4]diazepinols and Its Application to a Synthesis of Novel N-Sulfinylanilines
  作者：Yasuhiro Kamitori、Norio Ota、Takehisa Tomoda、Naoya Terai、Dai Shibata、Maurice Médebielle、Etsuji Okada

  DOI：10.3987/com-08-s(n)82

  日期：——
• Fluoro organics: Facile syntheses of novel 2- or 4-trifluoromethyl-1H-arylo-1,5-diazepines, oxazepines, thiazepines, 2 -(1,1,1-trifluoroacetonyl)imidazoles, oxazoles and thiazoles
  作者：A Chandra Sheker Reddy、P Shanthan Rao、R.V Venkataratnam

  DOI：10.1016/s0040-4020(97)00244-5

  日期：1997.4