2,2,2-三氟-1-(2-甲氧基-1-环戊烯-1-基)乙酮 | 158432-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2,2-三氟-1-(2-甲氧基-1-环戊烯-1-基)乙酮
• 英文名称: 2-trifluoroacetyl-1-methoxycyclopentene
• 英文别名: 2,2,2-Trifluoro-1-(2-methoxycyclopent-1-en-1-yl)ethan-1-one；2,2,2-trifluoro-1-(2-methoxycyclopenten-1-yl)ethanone
• CAS: 158432-46-3
• 化学式: C₈H₉F₃O₂
• 分子量: 194.153
• InChiKey: WXHFXYXDADBXDG-UHFFFAOYSA-N

物化性质

• 沸点：
  49-50 °C(Press: 2.4 Torr)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  2,2,2-三氟-1-(2-甲氧基-1-环戊烯-1-基)乙酮 在 盐酸羟胺 作用下， 以 盐酸 为溶剂， 反应 12.0h， 以71%的产率得到4,5-trimethylene-3-trifluoromethyl-5-hydroxy-4,5-dihydroisoxazole
  参考文献：
  名称：

  卤代乙酰化的烯醇醚。6 [5]。4,5-三亚甲基-4,5-二氢异恶唑的合成

  摘要：

  据报道，研究了环戊烷环对2-乙酰基环戊酮1a-d和β-甲氧基乙烯基三氟甲基酮衍生物2a与羟胺盐酸盐反应的区域化学的影响。该反应以良好的产率以区域特异性方式得到4,5-三亚甲基-4,5-二氢异恶唑3a-d。

  DOI：

  10.1002/jhet.5570330437
• 作为产物：
  描述：

  环戊酮 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 2,2,2-三氟-1-(2-甲氧基-1-环戊烯-1-基)乙酮
  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

• Haloacetylated enol ethers.<b>14</b>[6]. Reaction of β-alkoxyvinyl trifluoromethyl ketones with<i>N</i>-methylhydroxylamine
  作者：Marcos A. P. Martins、Alex F. C. Flores、Giovani P. Bastos、Nilo Zanatta、Helio G. Bonacorso

  DOI：10.1002/jhet.5570360402

  日期：1999.7

  The reaction of a series of β-methoxyvinyl trifluoromethyl ketones [CF3COC(R2)C(OMe)R1, where R1 = Me, -(CH2)3-C3, -CH2)4-C3, Ph and R2 = H, Me, -(CH2)3-C4, -(CH2)4-C4] with N-methylhydroxylamine is reported. The regiochemistry of the reaction are explained by MO calculation data.

  一系列β-甲氧基乙烯基三氟甲基酮[CF 3 COC（R 2）C（OMe）R 1的反应，其中R 1 = Me，-（CH 2）3 - C 3，-CH 2）4 - C 3中，Ph和R 2 = H，Me中， - （CH 2）3 - ç 4， - （CH 2）4 - C ^ 4] ñ -methylhydroxylamine报道。反应的区域化学由MO计算数据解释。
• 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。
• Synthesis of Alkyl-, Aryl- and Heteroaryl-Substituted 2-[3-Oxo-2,3-dihydro-1<i>H</i>-pyrazol-2-yl]-6(4)-trifluoromethylpyrimidines from β-Alkoxyvinyl Trifluoromethyl Ketones
  作者：Helio Bonacorso、Demétrius Martins、Marcos Martins、Nilo Zanatta、Alex Flores

  DOI：10.1055/s-2005-861824

  日期：——

  A general method for the synthesis of a novel series of 4-alkyl, 4-aryl, and 4-heteroaryl-substituted 2-[4-(2-hydroxyethyl)-5-methyl-3-oxo-2,3-dihydro-1H-pyrazol-2-yl]-6(4)-trifluoromethylpyrimidines, in 35-80% yields, by cyclocondensation of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones with 1-amidino-4-(2-hydroxyethyl)-3-methyl-3-pyrazolin-5-one in the presence of anhydrous potassium carbonate, is described.

  描述了一种通过4-烷氧基-1,1,1-三氟-3-烯-2-酮与1-氨基-4-(2-羟基乙基)-3-甲基-3-吡唑啉-5-酮在无水碳酸钾存在下进行环缩合，从而合成一系列新型4-烷基、4-芳基和4-杂芳基取代的2-[4-(2-羟基乙基)-5-甲基-3-氧代-2,3-二氢-1H-吡唑-2-基]-6(4)-三氟甲基嘧啶，收率在35-80%之间。
• Synthesis of Tetrahydro‐2(1<i>H</i>)quinazolinones, Cyclopenta[<i>d</i>]‐2(1<i>H</i>)pyrimidinones, and Their Thioxo Analogs from 2‐Trifluoroacetyl‐1‐methoxycycloalkenes
  作者：Helio G. Bonacorso、Michelle B. Costa、Itamar S. Lopes、Marlí R. Oliveira、Roberta L. Drekener、Marcos A. P. Martins、Nilo Zanatta、Alex F. C. Flores

  DOI：10.1080/00397910500278818

  日期：2005.12

  A series of six (8)-alkyl-4-trifluoromethyl-5,6,7,8-tetrahydro-2(1H)quinazolinones, 4-trifluoromethyl-cyclopenta[d]-2(1H)pyrimidinones, and their thioxo analogs from the reaction of five beta-alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan-2-ol as solvent and boron trifluoride diethyl etherate as catalyst in 18-65% yield.
• Synthesis, 17O NMR spectroscopy and structure of 2-trifluoroacetyl-1-methoxycycloalkenes
  作者：Helio G. Bonacorso、Michelle B. Costa、Sidnei Moura、Lucas Pizzuti、Marcos A.P. Martins、Nilo Zanatta、Alex F.C. Flores

  DOI：10.1016/j.jfluchem.2005.08.003

  日期：2005.10

  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.