1,1,1-trichloro-4-methoxy-5-methylhex-3-en-2-one | 470467-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1-trichloro-4-methoxy-5-methylhex-3-en-2-one
• CAS: 470467-28-8
• 化学式: C₈H₁₁Cl₃O₂
• 分子量: 245.533
• InChiKey: CURHRUPLVLVUBK-UHFFFAOYSA-N

物化性质

• 沸点：
  233.6±40.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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-5-methylhex-3-en-2-one 在 盐酸羟胺 作用下， 以 水 为溶剂， 反应 1.0h， 以91%的产率得到3-Isopropyl-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol
  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

• Regiospecific synthesis of 3<i>H</i>-pyrido[2,3-<i>b</i>][1,4]diazepin-4(5<i>H</i>)-ones<i>via</i>haloform reaction with the isolation of<i>N</i>³-[3-oxo-4,4,4-trichloroalk-1-en-1-yl]-2,3-diaminopyridine intermediates
  作者：Helio G. Bonacorso、Rogério V. Lourega、Liliane M. F. Porte、Everton D. Deon、Nilo Zanatta、Alex F. C. Flores、Marcos A. P. Martins

  DOI：10.1002/jhet.89

  日期：2009.7

  2-aryl/heteroaryl-3H-pyrido[2,3-b][1,4]diazepin-4(5H)-ones obtained from intramolecular cyclization reaction of the first series of trichloroacetyl enamines or from the direct cyclocondensation reaction of 4-methoxy-1,1,1-trichloalk-3-en-2-ones with 2,3-diaminopyridine, under mild conditions, is also demonstrated. J. Heterocyclic Chem., (2009).

  一系列新的类似的中间体的合成Ñ 3 - [1 -烷基（芳基/杂芳基）-3-氧代- 4,4,4- trichloroalk -1-烯-1-基] -2,3-二氨基吡啶和Ñ 2 - （甲磺酰基）[氯3 CC（O）CH CRNH（C 5 H ^ 3 N）NHY]，其中R = H中，Me，C 6 H ^ 5，4-FC 6 H ^ 4，4-CLC 6 ħ 4， 4- BRC 6 ħ 4，4-CH 3 C ^ 6 ħ 4，4-OCH 3 C ^ 6 ħ 4据报道，有4,4'-联苯，1-萘基，2-噻吩基，2-呋喃基，且Y ＝ H，SO 2 Me。从第一系列三氯乙酰基烯胺的分子内环化反应获得的新的相应系列的2-芳基/杂芳基-3 H-吡啶并[2,3- b ] [1,4]二氮杂-4-4（5 H）- 4-甲氧基-1,1,1-trichloalk-3-en-2-ones与还证明了在温和条件下的2，3-二氨基吡啶。J
• Evaluation of the synthesis of 1-(pentafluorophenyl)-4,5-dihydro-1H-pyrazoles using green metrics
  作者：Marcos A. P. Martins、Paulo H. Beck、Lilian Buriol、Clarissa P. Frizzo、Dayse N. Moreira、Mara R. B. Marzari、Marcileia Zanatta、Pablo Machado、Nilo Zanatta、Helio G. Bonacorso

  DOI：10.1007/s00706-013-0930-x

  日期：2013.7

  (CX3C(O)CH=C(R1)OR, where X = F, Cl; R = Me, Et; R1 = H, Me, Et, n-Pr, i-Pr, n-Bu, i-Pent, Ph, 4-Cl-C6H4, 4-Br-C6H4, 4-F-C6H4) with pentafluorophenyl hydrazine. Pyrazoles were obtained under microwave irradiation in solvent-free conditions or under conventional heating in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIM][BF4]. These procedures furnished products in moderate to good yields

  摘要1-（五氟苯基）-4,5-二氢-1 H-吡唑是根据4-烷氧基-1,1,1-三卤-3-烯丙基-2-酮的环缩合反应合成的（CX 3 C（O）CH = C（R 1）OR，其中X =氟，氯; R =甲基，乙基; R 1  = H，ME等，ñ -Pr，我-Pr，ñ -Bu，我-戊中，Ph，4- CL-C 6 H ^ 4，4 -溴-C 6 H ^ 4，4-FC 6 H ^ 4）与五氟苯基肼。吡唑是在无溶剂条件下于微波辐射下或在常规液体中于离子液体四氟硼酸1-丁基-3-甲基咪唑鎓[BMIM] [BF 4 ]中获得的。这些步骤在短的反应时间内以中等至良好的产率提供了产品。确定了在微波（MW）/无溶剂和常规热加热/ [BMIM] [BF 4 ]条件下进行的环缩合反应的原子经济性，反应质量效率（RME）和环境因子（E-factor）。RME和E因子表明，考虑到分离出的产物时，无溶剂程序的绿色始终低于[BMIM]
• Simplified Approach to the Regiospecific Synthesis of Trichloromethylpyrazolines Using Microwave Irradiation
  作者：Marcos A. P. Martins、Paulo Muraro、Paulo Beck、Pablo Machado、Clarissa P. Frizzo、Nilo Zanatta、Helio G. Bonacorso

  DOI：10.1080/00397910802162926

  日期：2008.9.29

  Twelve novel 3-alkyl[aryl]-1-carboxamides-5-trichloromethyl-5-hydroxy-4,5- dihydro-lH-pyrazole have been synthesized in good yields (72-90%) using environmentally benign microwave-induced techniques. The compounds were synthesized from the cyclocondensation of 4-alkoxy-1,1,1-trichloro-3- alkyl[aryl]-2-ones [Cl3CC(O)C(R-2)=C(R-1)OR, where R=Me, Et; R-1=H, Me, Et, Pr, i-Pr, i-Bu, t-Bu, Ph, Ph-4-NO2, Ph-4-F, Ph-4-Cl, Ph-4-Br; and R-2=H, Me] with semicarbazide hydrochloride in the presence of pyridine and using methanol/water (3:1 v/v) as the solvent. The advantages of using microwave irradiation, rather than a conventional method, were demonstrated.