methyl 3-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]propanoate | 1639427-86-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]propanoate
• CAS: 1639427-86-3
• 化学式: C₈H₁₀F₃NO₄
• 分子量: 241.167
• InChiKey: PLTMAURZGJCOMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙酰丙酸甲酯 在 吡啶 、 盐酸羟胺 、 对甲苯磺酸 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 methyl 3-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]propanoate
  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 Renewable Levulinic Acid to a Diversity of 3-(Azol-3-yl)Propanoates
  作者：Alex F. C. Flores、Luciana A. Piovesan、Lucas Pizzuti、Darlene C. Flores、Juliana L. Malavolta、Marcos A. P. Martins

  DOI：10.1002/jhet.1774

  日期：2014.5

  3‐(trihalomethylated‐1,2‐azol‐3‐yl)propanoate is reported. Preparation of the key methyl 7,7,7‐trihalo‐4‐methoxy‐6‐oxohept‐4‐enoate precursors from levulinic acid is also described. The synthetic potential of this synthetic protocol was indicated by the production of several methyl and ethyl 3‐(isoxazol‐3‐yl)propanoates and 3‐(1H‐pyrazol‐3‐yl)propanoates, and the respective acid derivatives, in good (70–95%)

  将7,7,7-三氟-4-甲氧基-6-氧代-4-庚烯酸甲酯和7,7,7-三氯-4-甲氧基-6-氧代-4-庚烯酸甲酯高效杂环化为异恶唑和吡唑衍生物代表报告了一种新型的谷氨酸样3-（三卤代甲基化1,2-氮杂-3-基）丙酸酯。还描述了从乙酰丙酸制备关键的7,7,7-三卤代-4-甲氧基-6-氧杂庚酸酯-甲基丙烯酸甲酯前体。这种合成规程的合成潜力通过生产3-（异恶唑-3-基）丙酸甲酯和乙酯和3-（1H-吡唑-3-基）丙酸酯和相应的酸衍生物来表明。 （70–95％）的产量。5-（3-乙氧基-3-氧丙基）-1 H-吡唑-3-羧酸乙酯的晶体结构（10c）是通过单晶X射线衍射分析确定的。N–H … H分子间氢键将分子连接到分解异构体中。