1,1,1-trichloro-4-methoxyhept-3-en-2-one | 436850-03-2

• 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-methoxyhept-3-en-2-one
• CAS: 436850-03-2
• 化学式: C₈H₁₁Cl₃O₂
• 分子量: 245.533
• InChiKey: SOHLZALFUTUEDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  239.1±40.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 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-methoxyhept-3-en-2-one 在 盐酸羟胺 作用下， 以 水 为溶剂， 反应 1.0h， 以93%的产率得到5-trichloromethyl-5-hydroxy-3-propyl-4,5-dihydroisoxazole
  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
• Regiospecific Bromination of 2-Phenyl-3<i>H</i>-pyrimidin-4-ones
  作者：Nilo Zanatta、Leonardo Fantinel、Liana Fernandes、Ana Wouters、Helio Bonacorso、Marcos Martins

  DOI：10.1055/s-0028-1083178

  日期：——

  Three methods for the regiospecific bromination of 2-phenyl-3H-pyrimidin-4-ones are presented: bromination of the 5-position of the pyrimidine ring, bromination of the 6-benzylic position and simultaneous bromination of both the 5-position of the pyrimidine ring and 6-benzylic position. Reactions were carried out using simple protocols and the brominated pyrimidines were obtained in good yields.

  本文介绍了 3 种 2-苯基-3H-嘧啶-4-酮的特异性溴化方法：嘧啶环 5 位溴化、6-苄基位溴化以及嘧啶环 5 位和 6-苄基位同时溴化。反应采用简单的方案进行，溴化嘧啶的收率很高。
• 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]
• Influence of bulky and halogen substituents on crystal packing of pyrazolo[1,5-a]pyrimidines
  作者：Clarissa P. Frizzo、Alexandre R. Meyer、Guilherme S. Caleffi、Letícia V. Rodrigues、Mara R.B. Marzari、Patrick T. Campos、Dayse N. Moreira、Helio G. Bonacorso、Nilo Zanatta、Marcos A.P. Martins

  DOI：10.1016/j.molstruc.2011.07.018

  日期：2011.10

  Abstract The crystalline structure of five 3-(R3) and/or 5-(R5)-substituted 7-trichloromethyl-2-methylpyrazolo[1,5-a]pyrimidines [where R3, R5 = H, Pr (1); Br, H (2); Br, Me (3); H, H (4); and H, Me (5)] were studied from X-ray diffractometry data. It was found that compounds presented themselves as main intermolecular interactions: Cl⋯Cl (1), Br⋯Cl (2,3); and Cl⋯N-pyrimidine (4,5). In compounds 1–3

  摘要 五个 3-(R3) 和/或 5-(R5)-取代的 7-三氯甲基-2-甲基吡唑并[1,5-a]嘧啶的晶体结构 [其中 R3, R5 = H, Pr (1); 溴，H（2）；溴，我（3）；H, H (4); 和 H, Me (5)] 是从 X 射线衍射数据中研究的。发现化合物本身表现为主要的分子间相互作用：Cl⋯Cl (1), Br⋯Cl (2,3)；和 Cl⋯N-嘧啶 (4,5)。在化合物1-3中，其他相互作用增强了晶体结构的稳定性，例如C-H⋯N-嘧啶（1,2）Cl⋯π-吡唑（1）；C-Br⋯π-嘧啶 (2); 和吡唑-π⋯π-嘧啶、嘧啶-π⋯π-嘧啶 (3)。该研究表明，化合物4和5中存在的Cl⋯N-嘧啶相互作用是典型的卤素⋯碱Lewis相互作用。Cl⋯Br和Cl⋯Cl相互作用的几何信息可以用σ-hole概念来解释。在化合物 2 中，氯原子与其σ-空穴一起参与，而在化合物3中，相互
• An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H-pyrazoles in ionic liquid
  作者：Dayse N. Moreira、Clarissa P. Frizzo、Kelvis Longhi、Nilo Zanatta、Helio G. Bonacorso、Marcos A. P. Martins

  DOI：10.1007/s00706-008-0874-8

  日期：2008.9

  The synthesis of eleven 1-cyanoacetyl-5-hydroxy-5-halomethyl-4,5-dihydro-1H-pyrazoles from the reaction of 4-alkoxy-3-alken-2-ones f((RC)-C-3(O)C(R-2) = C(R-1)OR, where R-3 = CF3, CCl3, CHCl2, CO2 Et; R-2/R-1 = H/H, H/Me, H/Et, -(CH2)(4)-, Me/H, H/Pr, and R = Me, Et) with cyanoacetohydrazide is reported. The reaction was carried out in the ionic liquid ([bmim][BF4]) and molecular solvents. The results showed that when the ionic liquid was used as reaction medium, the reaction time was drastically decreased and the yield was improved.