2,2,2-trichloro-1-(2-methoxycyclohexen-1-yl)ethanone | 158432-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trichloro-1-(2-methoxycyclohexen-1-yl)ethanone
• CAS: 158432-51-0
• 化学式: C₉H₁₁Cl₃O₂
• 分子量: 257.544
• InChiKey: HOSUSCBBLMDOQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,2,2-trichloro-1-(2-methoxycyclohexen-1-yl)ethanone 在 硫酸 、 盐酸羟胺 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-(Trichloromethyl)-4,5,6,7-tetrahydro-2,1-benzoxazole
  参考文献：
  名称：

  Synthesis in Water and Antimicrobial Activity of 5-Trichloromethyl-4,5-dihydroisoxazoles

  摘要：

  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.

  DOI：

  10.1080/00397911.2012.706349

文献信息

• New one-pot, efficient, and regioselective method for the synthesis of 3-Trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs
  作者：Helio G. Bonacorso、Michele S. Correa、Liliane M.F. Porte、Everton P. Pittaluga、Nilo Zanatta、Marcos A.P. Martins

  DOI：10.1016/j.tetlet.2012.07.119

  日期：2012.10

  An efficient and regioselective procedure for the synthesis of a series of alkyl(aryl/heteroaryl) substituted 3-trifluoromethyl-1H-1-phenylpyrazoles and alkyl 3-carboxylate analogs, from the cyclocondensation reactions of 4-alkoxy-1,1,1-trihaloalk-3-en-2-ones [CX3C(O)CR2=CR1(OMe/OEt), where R1 = H, Me, Ph, 2-Furyl; R2 = H; R1-R2 = -C4H8- and X = F, Cl] and 1-phenylsemicarbazide in an acidified alcoholic

  从4-烷氧基-1,1,1的环缩合反应合成一系列烷基（芳基/杂芳基）取代的3-三氟甲基-1 H -1-苯基吡唑和3-羧酸烷基酯类似物的有效和区域选择性程序-trihaloalk-3-en-2-ones [CX 3 C（O）CR 2 = CR 1（OMe / OEt），其中R 1 = H，Me，Ph，2-呋喃基；R 2＝ H；在酸性醇介质（R 3 OH / H 2 SO 4）中，R 1 -R 2 = -C 4 H 8-和X = F，Cl]和1-苯基氨基脲，其中R 3 = Me，Et，Pr i 已成功应用，并在此处进行了详细说明。