| 1594082-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1594082-98-0
• 化学式: C₁₄H₂₃Cl₃O₂
• 分子量: 329.694
• InChiKey: OACFBRNPCDMEHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  在 盐酸肼 作用下， 生成 methyl 3-nonyl-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Synthesis of Fatty Trichloromethyl-β-diketones and New 1H-Pyrazoles as Unusual FAMEs and FAEEs

  摘要：

  The efficient synthesis of new fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones [Cl3CC(O)C(R-2)=C(R-1)OMe, where R-1=n-hexyl, heptyl, nonyl, undecyl, tridecyl and R-2 = H] and 1,1,1-trichloro-2,4-alkanediones [Cl3CC(O)(CHRC)-C-2(O)R-1, where R-1 = n-pentyl and R-2 = Me, R-1 = Et and R-2 = n-butyl, R-1 = n-butyl and R-2 = n-propyl] in good yields (85-95%) from acetal acylation with trichloroacetyl chloride is reported. The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and 1,1,1-trichloro-2,4-alkanediones were reacted with hydrazine hydrochloride, leading to respective 1H-pyrazole-5-carboxylates, unusual class of fatty acid methyl (FAMEs) and ethyl (FAEEs) esters. Their structures were confirmed by elemental analysis and H-1 and C-13 nuclear magnetic resonance (NMR). The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and 1H-pyrazole derivatives are new oleochemicals with potentially interesting and differential properties.

  DOI：

  10.5935/0103-5053.20130237
• 作为产物：
  描述：

  2,2-二甲氧基十一烷 、 三氯乙酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Fatty Trichloromethyl-β-diketones and New 1H-Pyrazoles as Unusual FAMEs and FAEEs

  摘要：

  The efficient synthesis of new fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones [Cl3CC(O)C(R-2)=C(R-1)OMe, where R-1=n-hexyl, heptyl, nonyl, undecyl, tridecyl and R-2 = H] and 1,1,1-trichloro-2,4-alkanediones [Cl3CC(O)(CHRC)-C-2(O)R-1, where R-1 = n-pentyl and R-2 = Me, R-1 = Et and R-2 = n-butyl, R-1 = n-butyl and R-2 = n-propyl] in good yields (85-95%) from acetal acylation with trichloroacetyl chloride is reported. The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and 1,1,1-trichloro-2,4-alkanediones were reacted with hydrazine hydrochloride, leading to respective 1H-pyrazole-5-carboxylates, unusual class of fatty acid methyl (FAMEs) and ethyl (FAEEs) esters. Their structures were confirmed by elemental analysis and H-1 and C-13 nuclear magnetic resonance (NMR). The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and 1H-pyrazole derivatives are new oleochemicals with potentially interesting and differential properties.

  DOI：

  10.5935/0103-5053.20130237

文献信息

• Synthesis of 2,2,2-trifluoroethyl 1H-pyrazole carboxylates: Insight into the mechanism of trichloromethyl group hydrolysis
  作者：Helena A. Gonçalves、Bruna A. Pereira、Wystan K.O. Teixeira、Sidnei Moura、Darlene C. Flores、Alex F.C. Flores

  DOI：10.1016/j.jfluchem.2016.05.009

  日期：2016.7

  one-pot synthesis of 2,2,2-trifluoroethyl 1H-pyrazole-5(3)-carboxylates via cyclocondensation of 1,1,1-trichloro-4-alkoxy-3-alken-2-ones [Cl3CC(O)C(R2) = C(R1)OMe, where R1 = H, CH3, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, −(CH2)2Ph, 4-ClC6H4, 4-BrC6H4 and R2 = H] and 1,1,1-trichloro-2,4-alkanediones, 1-aryl-4,4,4-trichloro-1,3-butanediones [Cl3CC(O)CHR2C(O)R1, where R1 = H, CH3, −(CH2)2Ph

  本文报道了通过1,1,1-三氯-4-烷氧基-3-烯烃-2-酮的环缩合反应一锅法合成2,2,2-三氟乙基1H-吡唑-5（3）-羧酸盐[Cl 3 CC（O）C（R 2）= C（R 1）OME，其中R 1  = H，CH 3，ñ辛基，ñ壬基，ñ癸基，ñ -十一烷基，正-十三烷基， - （CH 2）2 Ph，4-ClC 6 H 4，4 -BrC 6 H 4和R 2  = H]和1,1,1-三氯-2,4-烷二酮，1-芳基-4,4,4-三氯- 1,3-丁二酮[Cl3 CC（O）CHR 2 C（O）R 1，其中R 1  = H，CH 3， - （CH 2）2 PH，PH，4-FC 6 H ^ 4 ， 4- BRC 6 ħ 4，R 2  = H，R 1  ＝ Ph，R 2  ＝ CH 3，R 1，R 2  ＝环-（CH 2）5-]与盐酸肼在2,2,2-三氟乙醇（TFE）中的混合。考虑到TFE相对于甲醇或乙醇的低亲核性，该结果为连接在1
• An Acetal Acylation Methodology for Producing Diversity of Trihalomethyl- 1,3‑dielectrophiles and 1,2-Azole Derivatives
  作者：Valéria Bareño、Daiane Santos、Leandro Frigo、Debora de Mello、Juliana Malavolta、Rogerio Blanco、Lucas Pizzuti、Darlene Flores、Alex Flores

  DOI：10.21577/0103-5053.20190160

  日期：——

  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.