1,1,1-trichloro-4-ethoxy-3-methyl-3-buten-2-one | 83124-84-9

• 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-ethoxy-3-methyl-3-buten-2-one
• 英文别名: 1,1,1-trichloro-4-ethoxy-3-methylbut-3-en-2-one
• CAS: 83124-84-9
• 化学式: C₇H₉Cl₃O₂
• mdl: MFCD22989162
• 分子量: 231.506
• InChiKey: BGHXUMZQYBZECU-UHFFFAOYSA-N

物化性质

• 沸点：
  219.3±40.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1,1-trichloro-4-ethoxy-3-methyl-3-buten-2-one 、 N-甲基脲 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以60%的产率得到1,5-dimethyl-4-(trichloromethyl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  N-Alkyl-4-(trihalomethyl)-1H-pyrimidin-2-ones合成的化学选择性和产率的比较研究

  摘要：

  本文报道了通过 4-烷氧基-1,1,1-三卤代环缩合反应合成 N-烷基-4-(三卤甲基)-1H-嘧啶-2-酮的化学选择性和产率的比较研究。 3-alken-2-ones（烯酮）与甲基-和烯丙基脲，4-（三卤甲基）-1H-pyrimidin-2-ones 与甲基碘和烯丙基溴的 N-烷基化。为了确定所得产物的化学选择性，所有化合物均通过 1H 和 13C NMR 以及 2D HMBC 光谱进行了全面分析。该研究表明，环缩合反应产生更好的产率并提供 N1-或 N3-烷基化产物，这取决于反应条件和烯酮上的取代基，而嘧啶-2-酮的烷基化产生较低的总产率和N1-烷基化产物或N1-和O-烷基化产物的混合物。

  DOI：

  10.1002/ejoc.200800822
• 作为产物：
  描述：

  (E)-1-ethoxyprop-1-ene 、 三氯乙酰氯 在 三乙胺 作用下， 生成 1,1,1-trichloro-4-ethoxy-3-methyl-3-buten-2-one
  参考文献：
  名称：

  Effenberger, Franz; Maier, Roland; Schoenwaelder, Karl-Heinz, Chemische Berichte, 1982, vol. 115, p. 2766 - 2782

  摘要：

  DOI：

文献信息

• A simple one-pot synthesis of 3-alkoxy-3-cyanocarboxylic acids: a rapid entry to new GABA derivatives
  作者：Nilo Zanatta、Fabio M. da Silva、Luciana S. da Rosa、Louíse Jank、Helio G. Bonacorso、Marcos A.P. Martins

  DOI：10.1016/j.tetlet.2007.07.060

  日期：2007.9

  A simple one-pot procedure to obtain a series of new 3-alkoxy-3-cyanocarboxylic acids from the reaction of 4-alkoxy-1,1,1-trichloro-but-3-en-2-ones with sodium cyanide is described.

  描述了一种简单的一锅法，该方法可从4-烷氧基-1,1,1-三氯-丁-3-烯-2-酮与氰化钠的反应中获得一系列新的3-烷氧基-3-氰基羧酸。
• Synthesis and Characterization of Some Novel 2-(Trifluoromethyl)pyrimido[1,2-<b><i>a</i></b>]benzimidazoles and Pyrimido[1,2-<b><i>a</i></b>]benzimidazol-2<b><i>H</i></b>)-ones of Biological Interest
  作者：Nilo Zanatta、Aurea Echevarria、Simone Amaral、Andressa Esteves-Souza、Patrícia Brondani、Darlene Flores、Helio Bonacorso、Alex Flores、Marcos Martins

  DOI：10.1055/s-2006-942444

  日期：——

  The synthesis of some potentially active 2-(trifluoro-methyl)pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-a]benzimidazol-2(1H)-ones by the cyclization of 4-alkoxyvinyl trifluoro(chloro)methyl ketones with 2-aminobenzimidazole is described. The structure of the products was assigned based on 'H and 13 C NMR as well as 2D-NMR experiments. Some of the obtained products exhibited significant DNA-topoisomerase

  4-烷氧基乙烯基三氟(氯)环化合成一些具有潜在活性的2-(三氟甲基)嘧啶并[1,2-a]苯并咪唑和嘧啶并[1,2-a]苯并咪唑-2(1H)-one描述了具有 2-氨基苯并咪唑的甲基酮。产物的结构基于 1H 和 13 C NMR 以及 2D-NMR 实验确定。一些获得的产物表现出显着的DNA-拓扑异构酶I抑制活性。
• Synthesis and structural study of a new series of 2‐methylsulfanyl‐tetrahydropyrimidines from β‐alkoxyvinyl trihalomethyl ketones
  作者：Nilo Zanatta、Claudia C. Madruga、Patricia C. Marisco、Luciana S. Da Rosa、Liana Da S. Fernandes、Darlene C. Flores、Alex F. C. Flores、Robert A. Burrow、Helio G. Bonacorso、Marcos A P. Martins

  DOI：10.1002/jhet.5570450127

  日期：2008.1

  This work describes the synthesis of a novel series of 2-methylsulfanyl-tetrahydropyrimidines, from the cyclocondensation reaction of β-alkoxyvinyl trihalomethyl ketones with 2-methyl-2-thiopseudourea sulfate, in good yields. A detailed 1H- and 13C-NMR study was performed on the 2-methylsulfanyl-tetrahydropyrimidines obtained and 3D structures were proposed based on AM1 calculations supported by 1H

  这项工作描述了由β-烷氧基乙烯基三卤代甲基酮与2-甲基-2-硫代伪脲硫酸盐的高产率的环缩合反应，合成一系列新的2-甲基硫烷基-四氢嘧啶。对获得的2-甲基硫烷基-四氢嘧啶进行了详细的1 H-和13 C-NMR研究，并基于1 H NMR偶联常数和NOESY实验支持的AM1计算，提出了3D结构。
• An Efficient Two-Step Synthesis of New 5-Substituted-1<i>H</i>-tetrazoles of Biological Interest
  作者：Nilo Zanatta、Fabio M. da Silva、Andreia M. P. W. da Silva、Estefania da C. Aquino、Helio G. Bonacorso、Marcos A. P. Martins

  DOI：10.1002/jhet.1711

  日期：2013.7

  A simple procedure for the synthesis and characterization of new 3‐alkoxy‐3‐(1H‐tetrazol‐5‐yl)propionic acids and 2‐(1H‐tetrazol‐5‐yl)tetrahydrofuran‐ and ‐(1H‐tetrazol‐5‐yl)‐2H‐pyran‐3‐carboxylic acids from the [2 + 3] cycloaddition reactions between the nitrile group of β‐cyanocarboxylic acids with sodium azide in the presence of zinc chloride is described. The tetrazolic acids were isolated in moderate

  合成和表征新的3-烷氧基-3-（1 H-四唑-5-基）丙酸和2-（1 H-四唑-5-基）四氢呋喃和-（1 H-四唑）的简单程序描述了在氯化锌的存在下，β-氰基羧酸的腈基与叠氮化钠之间[2 + 3]环加成反应中的[ -5-基] -2 H-吡喃-3-羧酸。以中等至良好的产率分离出四唑酸，并且在结构上类似于琥珀酸。
• Experimental and calculated structural parameters of 5-trihalomethyl-4,5-dihydro-1H-pyrazole derivatives, novel analgesic agents
  作者：Pablo Machado、Patrick T. Campos、Glauber R. Lima、Fernanda A. Rosa、Alex F.C. Flores、Helio G. Bonacorso、Nilo Zanatta、Marcos A.P. Martins

  DOI：10.1016/j.molstruc.2008.07.016

  日期：2009.1

  The crystal structures of four novel analgesic agents, methyl 5-hydroxy-3- or 4-methyl-5-trichloro[trifluoro]methyl-4,5-dihydro-1H-pyrazole-1-carboxylate, have been determined by X-ray diffractometry. The data demonstrated that the molecular packing was stabilized mainly by O-H center dot center dot center dot O hydrogen bonds of the 5-hydroxy and 1-carboxymethyl groups. The 4,5-dihydro-1H-pyrazole rings were obtained as almost planar structures showing RMS deviation at a range of 0.0052-0.0805 angstrom. Additionally, computational investigation using semi-empirical AM1 and PM3 methods were performed to find a correlation between experimental and calculated geometrical parameters. The data obtained suggest that the structural data furnished by the AM1 method is in better agreement with those experimentally determined for the above Compounds. (c) 2008 Elsevier B.V. All rights reserved.