5-trichloromethyl-5-hydroxy-3-(1-thiomethylethyl)-4,5-dihydroisoxazole | 1445753-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 5-trichloromethyl-5-hydroxy-3-(1-thiomethylethyl)-4,5-dihydroisoxazole
• 英文别名: 3-(1-methylsulfanylethyl)-5-(trichloromethyl)-4H-1,2-oxazol-5-ol
• CAS: 1445753-82-1
• 化学式: C₇H₁₀Cl₃NO₂S
• 分子量: 278.587
• InChiKey: XBUXJGKQJDCLMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲巯基-2-丁酮 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 5-trichloromethyl-5-hydroxy-3-(1-thiomethylethyl)-4,5-dihydroisoxazole
  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

• Synthesis in Water and Antimicrobial Activity of 5-Trichloromethyl-4,5-dihydroisoxazoles
  作者：Alex F. C. Flores、Luciana A. Piovesan、Alynne A. Souto、Mariano A. Pereira、Marcos A. P. Martins、Tatiane L. Balliano、Givanildo S. da Silva

  DOI：10.1080/00397911.2012.706349

  日期：2013.9.2

  Two series of 5-trichloromethylisoxazoles were synthesized from the cyclocondensation of 1,1,1-trichloro-4-methoxy-3-alken-2-ones [Cl3CC(O)C(R-2)=C(R-1)OMe, where R-1=H, Me, Et, Pr, iso-Pr, cyclo-Pr, Bu, terc-Bu, CH2Br, CHBr2, CH(Me)SMe, (CH2)(2)Ph, and Ph, and R-2=H; R-1=H and R-2=Me and Et; R-1 and R-2=-(CH2)(4)- and -(CH2)(5)-; and R-1=Et and Ph and R-2=Me] with hydroxylamine hydrochloride through a rapid one-pot reaction in water. The 5-trichloromethyl-4,5-dihydroisoxazoles were aromatized by reaction with concentrated sulfuric acid to obtain the respective 5-trichloromethylisoxazoles. Their structures were confirmed by elemental analysis, H-1/C-13 nuclear magnetic resonance, and electron impact mass spectroscopy. Crystal structure analysis for 5-triclhoromethyl-5-hydroxy-3-propyl-4,5-dihydroisoxazole (2d) and 5-trichloromethyl-5-hydroxy-3,4-hexamethylene-4,5-dihydroisoxazole (2o) is presented. The antimicrobial activities of the 5-trichloromethyl-4,5-dihydroisoxazole derivatives were examined using the standard twofold dilution method against Gram-positive bacteria (Staphylococcus aureus), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and yeasts (Candida spp. and Cryptococcus neoformans). All of the tested 5-trichloromethyldihydroisoxazoles exhibited antibacterial and antifungal activities at the tested concentrations. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• 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.