2-trifluoroacetyl-1-methoxycycloheptene | 881020-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-trifluoroacetyl-1-methoxycycloheptene
• 英文别名: 2,2,2-Trifluoro-1-(2-methoxycyclohepten-1-yl)ethanone；2,2,2-trifluoro-1-(2-methoxycyclohepten-1-yl)ethanone
• CAS: 881020-28-6
• 化学式: C₁₀H₁₃F₃O₂
• 分子量: 222.207
• InChiKey: PHVCPFRFTVLURG-UHFFFAOYSA-N

物化性质

• 沸点：
  83-85 °C(Press: 1.8 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-trifluoroacetyl-1-methoxycycloheptene 在 吡啶 、 盐酸羟胺 作用下， 以 水 为溶剂， 反应 24.0h， 以85%的产率得到3-hydroxy-3-trifluoromethyl-3H-3a,4,5,6,7,8-hexahydro-cyclohepta[c]isoxazole
  参考文献：
  名称：

  2-三氟乙酰基-1-甲氧基环烯烃：方便的前体，用于合成发芽的聚亚甲基三氟甲基取代的杂环

  摘要：

  本文介绍了允许同时引入三氟甲基和稠合到杂环衍生物的7、8和10元环烷烃环的方法。由三种衍生自下列物质的2-三氟乙酰基-1-甲氧基环烯烃的反应以中等至良好的收率获得了一系列10个由聚亚甲基三氟甲基取代的异恶唑啉，吡唑，嘧啶酮和吡唑基-喹啉的衍生物环庚酮，辛酮和环十二酮与羟胺盐酸盐，盐酸肼，尿素和7-氯-4-肼基喹啉。J.杂环化​​学，（2009）。

  DOI：

  10.1002/jhet.66
• 作为产物：
  描述：

  环庚酮 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 40.0h， 生成 2-trifluoroacetyl-1-methoxycycloheptene
  参考文献：
  名称：

  Synthesis, 17O NMR spectroscopy and structure of 2-trifluoroacetyl-1-methoxycycloalkenes

  摘要：

  Among the synthesis of a series of five well-known 2-trifluoroacetyl-1-methoxycycloalkenes derived from cyclopentanone and substituted cyclohexanones, this paper describes the synthesis of three new 2-trifluoroacetyl-1-methoxycycloalkenes derived from cycloheptanone, cyclooctanone and cyclododecanone in 60-68% yield. Subsequently, the O-17 NMR chemical shift analysis of the carbonyl and the methoxy groups for these cyclic molecules clearly showed the electron push-pull phenomenon and revealed large and irregular variations of O-17 NMR chemical shifts with the ring size. Finally, a more stable conformation of these trifluoroacetyl-containing cycloalkenes was determined by energy minimization calculations using Austin Model 1 (AM1) semi-empirical method and correlations between O-17 NMR data and torsion angles or oxygen net charge calculated by AMI semi-empirical method were performed. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.08.003

文献信息

• General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues
  作者：Helio G. Bonacorso、Rosália Andrighetto、Nícolas Krüger、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.3390/molecules16042817

  日期：——

  A convenient and general method for the synthesis in 26–73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R1)OR, where R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furyl, 2-thienyl and R = Me, Et] with 2,6-diaminopyridine (2,6-DAP), under mild

  从 4-烷氧基-的直接环缩合反应合成新系列 7-烷基（芳基/杂芳基）-2-氨基-5-三氟甲基-1,8-萘啶的简便通用方法，产率为 26-73% 1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R1)OR, 其中 R1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4描述了 -BrPh、4-NO2Ph、2-呋喃基、2-噻吩基和 R = Me, Et] 与 2,6-二氨基吡啶 (2,6-DAP) 在温和条件下的反应。另一种合成路线还允许从五、六和七的直接或间接环缩合反应合成 2-氨基-5-三氟甲基-环烷[b][1,8]萘啶，产率为 33-36%。 2-三氟乙酰基-1-甲氧基-环烯烃与 2,6-DAP。
• From Levulinic Acid to Biheterocycles: Synthesis of 1-[(5-Hydroxy-5-trifluoromethyl-3-substituted-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)-3-(5-trifluoromethyl-1<i>H-</i>pyrazol-3-yl)propan-1-ones
  作者：Alex F. C. Flores、Juliana L. Malavolta、Leandro M. Frigo、Morgana Doneda、Darlene C. Flores

  DOI：10.1080/00397911.2014.1003352

  日期：2015.5.19

  We develop an efficient method to synthesize novel propionyl-spaced bisheterocyclic compounds. It entails cyclocondensation of 3-(5-trifluoromethyl-1H-pyrazol-3-yl)propanoyl hydrazide obtained from levulinic acid, with 1,1,1-trifluoro-4methoxy-3-alken-2-ones proceeding regiospecifically to 1-[(5-trifluoromethyl-5-hydroxy3-substituted-4,5-dihydro-1H-pyrazol-1-yl)-3-(5-trifluoromethyl-1H-pyrazol-3-yl)propan- I-one derivatives.
• Efficient Synthesis of New Biheterocyclic 5-[(5-Trifluoromethyl-5-hydroxy-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoromethylpyrazolo[1,5-<i>α</i>]pyrimidines
  作者：Alex F. C. Flores、Pauline F. Rosales、Juliana L. Malavolta、Darlene C. Flores

  DOI：10.5935/0103-5053.20140126

  日期：——
• Efficient synthesis of new biheterocyclic 1-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-3-(6-trifluoro methylpyrimidin-4-yl)-propan-1-ones
  作者：Juliana L. Malavolta、Alynne A. Souto、Debora L. de Mello、Darlene C. Flores、Alex F.C. Flores

  DOI：10.1016/j.jfluchem.2013.11.014

  日期：2014.2

  Several new 1-(5-hydroxy-5-trifluoromethyl-1H-pyrazol-1-yl)-3-(6-trifluoromethyl pyrimidin-4-yl)-propan-1-ones were prepared by cyclocondensation between two different 3-[6-trifluoromethyl-2(substituted)pyrimidin-4-yl]propanoylhydrazides derived from levulinic acid and versatile 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones. The structure of new propionyl-spaced bis trifluoromethylated biheterocycles was characterized based on H-1 and C-13 nuclear magnetic resonance spectroscopy and mass spectrometry data. (C) 2013 Elsevier B.V. All rights reserved.
• One‐pot synthesis of <i>N</i> ² ‐aminoprotected 6‐substituted and cycloalka[ <i>d</i> ] 4‐trifluoromethyl‐2‐acetylaminopyrimidines
  作者：Helio G. Bonacorso、Adriana Ferla、Cleber A. Cechinel、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.1002/jhet.5570450228

  日期：2008.3

  Abstractmagnified imageThe one‐pot synthesis of a novel series of amino‐protected 6‐alkyl‐, 6‐aryl‐, 6‐heteroaryl‐ and 5,6‐fused‐cycloalkane 4‐trifluoromethyl‐2‐acetylaminopyrimidines, where alkyl = Me; aryl = Ph, 4‐CH3Ph, 4‐FPh, 4‐ClPh, 4‐BrPh, 4‐OCH3Ph, 4‐NO2Ph, 4,4′‐biphenyl, 1‐naphthyl; heteroaryl = 2‐thienyl, 2‐furyl and cycloalkyl = c‐C6H4, c‐C7H5 from the reaction of substituted 4‐methoxy‐1,1,1‐trifluoroalk‐3‐en‐2‐ones with 1‐acetylguanidine in acetonitrile or propan‐2‐ol as solvent, is reported. The acetylamino group of 2‐acetylaminopyrimidines was hydrolyzed under three different conditions to afford the corresponding free 2‐aminopyrimidines.