1,1,1-trichloro-4-methoxy-6-phenyl-3-hexen-2-one | 1445753-84-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 1,1,1-trichloro-4-methoxy-6-phenyl-3-hexen-2-one
• 英文别名: 1,1,1-trichloro-4-methoxy-6-phenylhex-3-en-2-one
• CAS: 1445753-84-3
• 化学式: C₁₃H₁₃Cl₃O₂
• 分子量: 307.604
• InChiKey: JQVUTKKNMKLBRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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-trichloro-4-methoxy-6-phenyl-3-hexen-2-one 在 水 作用下， 生成 1,1,1-trichloro-6-phenyl-2,4-hexanedione
  参考文献：
  名称：

  2,2,2-三氟乙基1 H-吡唑羧酸酯的合成：对三氯甲基水解机理的认识

  摘要：

  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

  DOI：

  10.1016/j.jfluchem.2016.05.009
• 作为产物：
  描述：

  苄基丙酮 在 吡啶 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 生成 1,1,1-trichloro-4-methoxy-6-phenyl-3-hexen-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

• 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.