1,1,1-trifluoro-4-methoxy-8-methylnona-3,7-dien-2-one | 1544273-18-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,1,1-trifluoro-4-methoxy-8-methylnona-3,7-dien-2-one
• 英文别名: 1,1,1-trifluoro-4-methoxy-8-methylnon-3,7-dien-2-one
• CAS: 1544273-18-8
• 化学式: C₁₁H₁₅F₃O₂
• 分子量: 236.234
• InChiKey: ZOIKMHUJSHINMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-4-methoxy-8-methylnona-3,7-dien-2-one 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  An Acetal Acylation Methodology for Producing Diversity of Trihalomethyl- 1,3‑dielectrophiles and 1,2-Azole Derivatives

  摘要：

  A series of functionalized 1,1,1-trihalo-4-methoxy-3-alken-2-ones [CX3C(O)CR1=CROMe, where X = F or Cl; R = n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, (CH2)(2)CH=C(Me)(2), (CH2)(2)Ph, (CH2)(2)-(4-HOC6H4), (CH2)(2)-(4-MeOC6H4), (CH2)(2)CO2Me, (CH2)(3)CO2Me, CH(SMe)CH3, CH2(2-MeOC6H4), and R-1 = H, and R = H and R-1 = n-decyl] were synthesized from respective alkyl methyl ketones or aldehyde via acetal acylation using trifluoroacetic anhydride and trichloroacetyl chloride. 1,1,1-Trihalo-4-methoxy-3-alken-2-ones with acid-compatible substituents were easily hydrolyzed to respective trihalomethyl-1,3-diketones. The 1,1,1-trihalo-4-methoxy-3-alken-2-ones and/or respective trihalomethyl-1,3-diketones were reacted regiospecifically with hydroxylamine hydrochloride, leading to isoxazole derivatives, and with hydrazines, leading to respective 1H-pyrazole derivatives. The structures of all compounds were assigned based on nuclear magnetic resonance (NMR) and mass spectrometric data. This method represents an efficient pathway for the regioselective trihaloacetylation of asymmetrically substituted alkyl methyl ketones and highly self-condensing aldehydes. Moreover, this approach allows the introduction of biologically recognizable moieties, such as those from levulinic acid, sulcatone (prenyl), benzylacetone, anisylacetone, and raspberry ketone, as synthetic molecular targets.

  DOI：

  10.21577/0103-5053.20190160
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 在 吡啶 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 生成 1,1,1-trifluoro-4-methoxy-8-methylnona-3,7-dien-2-one
  参考文献：
  名称：

  An Acetal Acylation Methodology for Producing Diversity of Trihalomethyl- 1,3‑dielectrophiles and 1,2-Azole Derivatives

  摘要：

  A series of functionalized 1,1,1-trihalo-4-methoxy-3-alken-2-ones [CX3C(O)CR1=CROMe, where X = F or Cl; R = n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, (CH2)(2)CH=C(Me)(2), (CH2)(2)Ph, (CH2)(2)-(4-HOC6H4), (CH2)(2)-(4-MeOC6H4), (CH2)(2)CO2Me, (CH2)(3)CO2Me, CH(SMe)CH3, CH2(2-MeOC6H4), and R-1 = H, and R = H and R-1 = n-decyl] were synthesized from respective alkyl methyl ketones or aldehyde via acetal acylation using trifluoroacetic anhydride and trichloroacetyl chloride. 1,1,1-Trihalo-4-methoxy-3-alken-2-ones with acid-compatible substituents were easily hydrolyzed to respective trihalomethyl-1,3-diketones. The 1,1,1-trihalo-4-methoxy-3-alken-2-ones and/or respective trihalomethyl-1,3-diketones were reacted regiospecifically with hydroxylamine hydrochloride, leading to isoxazole derivatives, and with hydrazines, leading to respective 1H-pyrazole derivatives. The structures of all compounds were assigned based on nuclear magnetic resonance (NMR) and mass spectrometric data. This method represents an efficient pathway for the regioselective trihaloacetylation of asymmetrically substituted alkyl methyl ketones and highly self-condensing aldehydes. Moreover, this approach allows the introduction of biologically recognizable moieties, such as those from levulinic acid, sulcatone (prenyl), benzylacetone, anisylacetone, and raspberry ketone, as synthetic molecular targets.

  DOI：

  10.21577/0103-5053.20190160

文献信息

• 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.