4-(1-naphthyl)-1,1,1-trifluoro-4-methoxybut-3-en-2-one | 868662-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(1-naphthyl)-1,1,1-trifluoro-4-methoxybut-3-en-2-one
• 英文别名: 1,1,1-trifluoro-4-methoxy-4-naphthalen-1-ylbut-3-en-2-one
• CAS: 868662-40-2
• 化学式: C₁₅H₁₁F₃O₂
• 分子量: 280.246
• InChiKey: IHMYOTYCMWBXCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  4-(1-naphthyl)-1,1,1-trifluoro-4-methoxybut-3-en-2-one 、 2,3-二氨基吡啶 以 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到N³-[1-(1-naphthyl)-3-oxo-4,4,4-trifluorobut-1-en-1-yl]-2,3-diaminopyridine
  参考文献：
  名称：

  新的2-氨基-和2,3-二氨基吡啶三氟乙酰基烯胺衍生物的制备及其在含三氟甲基的3 H-吡啶并[2,3- b ] [1,4]二氮杂醇中的应用

  摘要：

  一系列新型中间体N 2（N 3）-[1-烷基（芳基/杂芳基）-3-氧代-4,4,4-三氟烷-1-烯-1-基] -2-氨基吡啶的合成[F 3 CC（O）CH CR 1（2 NH C 5 H 3 N）]和2,3-二氨基吡啶[F 3 CC（O）CH CR 1（2-NH 2 -3-NH C 5 H 3 N ）]，其中R 1 = H中，Me，C 6 H ^ 5，4-FC 6 H ^ 4，4-CIC 6 ħ 4，4- BRC 6ħ 4，4-CH 3 C ^ 6 ħ 4，4-OCH 3 C ^ 6 ħ 4，4,4'-联苯基，1-萘基，2-噻吩基，2-呋喃基报道。从相应的三氟乙酰基烯胺的分子内环化反应或直接得到的2-芳基（杂芳基）-4-三氟甲基-3 H-吡啶并[2,3- b ] [1,4]二氮杂-4-醇的相应系列还报道了在温和条件下4-甲氧基-1,1,1-三氟烷-3-烯-2-酮与2,3-二氨基吡啶的环缩合反应。

  DOI：

  10.1002/jhet.5570450619
• 作为产物：
  描述：

  1-萘基甲醛二甲基缩醛 、 三氟乙酸酐 以 吡啶 、 氯仿 为溶剂， 反应 16.0h， 以81%的产率得到4-(1-naphthyl)-1,1,1-trifluoro-4-methoxybut-3-en-2-one
  参考文献：
  名称：

  一种高效且区域特异性的三氟甲基取代的4-（1 H-吡唑-1-基）-7-氯喹啉

  摘要：

  一系列新的4- [3-烷基（芳基）（杂芳基）-5-羟基-5-三氟甲基-4,5-二氢-1 H-吡唑-1-基] -7-氯喹啉，其中[烷基= CH 3；芳= C 6 H ^ 5，4-CH 3 C ^ 6 ħ 4，4-FC 6 H ^ 4，4-CLC 6 ħ 4，4- BRC 6 ħ 4，4-CH 3 OCgH 4，4-NO 2 CGH 4，4-联苯基，1-萘基；杂芳基＝ 2-呋喃基和2-噻吩基]是由7-氯-4-肼基喹啉与4-取代的-1,1,1-三氟-4-甲氧基丁-3-en-2-的反应在区域上确定的。收率为61-96％。随后，在酸性条件下4,5-二氢吡喃-唑基喹啉的脱水反应在73-96中提供了一系列新的4-（3-取代的5-三氟甲基-1 H-吡唑-基-1-基）-7-氯喹啉。 ％ 屈服。

  DOI：

  10.1002/jhet.5570420604

文献信息

• Regioselective synthesis and antimicrobial evaluation of new 1-aryloxyacetyl-, 1-thiophenoyacetyl- and 1-phenylaminoacetyl-substituted 3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazoles
  作者：Helio Gauze Bonacorso、Everton P. Pittaluga、Sydney H. Alves、Larissa F. Schaffer、Susiane Cavinatto、Liliane M. F. Porte、Gisele R. Paim、Marcos A. P. Martins、Nilo Zanatta

  DOI：10.3998/ark.5550190.0013.806

  日期：——

  regioselective synthesis of new series of twenty 1-aryloxy(thio)acetyl and 1-(phenylamino)acetyl-substituted 5-trifluoromethyl-5hydroxy-4,5-dihydro-1H-pyrazoles (3) in 34–96% yields from the cyclocondensation reaction of 4-alkoxy-4-alkyl-(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones with different substituted acetohydrazides. Dehydration reactions of 3, carried out in the presence of thionyl chloride, furnished

  本文描述了一种区域选择性合成新系列 20 个 1-芳氧基（硫代）乙酰基和 1-（苯氨基）乙酰基取代的 5-三氟甲基-5羟基-4,5-二氢-1H-吡唑 (3) 的有效方法4-烷氧基-4-烷基-（芳基/杂芳基）-1,1,1-三氟烷-3-en-2-酮与不同取代乙酰肼的环缩合反应产率为34-96%。在亚硫酰氯存在下进行的 3 的脱水反应提供了两个芳香族 5-三氟甲基-1H-吡唑衍生物的例子，产率为 78-82%。抗菌试验证明，白色念珠菌对 1-(苯基氨基)乙酰基取代的 3-烷基-2-吡唑啉衍生物的作用特别敏感；然而，与标准药物相比，最初的结果仍然很弱。
• An Easy Approach to the Synthesis of New Fused 3-Aryl-5- trifluoromethyl-7,8-dihydro-6H-thieno [2,1-f] [1,2] thiazine 1-Oxide System
  作者：Helio Bonacorso、Renata Vezzosi、Roberta Drekener、Nilo Zanatta、Marcos Martins

  DOI：10.2174/157017809787582726

  日期：2009.3.1

  A new series of 4-alkyl(aryl)-4-tetramethylenesulfoximide-1,1,1-trifluoroalk-3-en-2-ones has been prepared from the O,N-exchange reactions of 4-alkyl(aryl)-4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones with the cyclic S,Stetramethylenesulfoximide in absence of solvent, in good yields. Subsequently, the easy preparation of a new series of a fused heterocyclic system of 3-aryl-5-trifluoromethyl-7,8-dihydro-6H-thieno[2,1-f][1,2]thiazine 1-oxide derivatives (60- 85% yields) from intramolecular cyclization reactions of sulfoximide enones employing potassium t-butoxide in diethyl ether at reflux is also reported.

  通过 4-烷基（芳基）-4-烷氧基-1,1,1-三氟烷基-3-烯-2-酮与环状 S,Stetramethylenesulfoximide（四甲基亚磺酰亚胺）在无溶剂条件下发生 O,N-交换反应，制备了一系列新的 4-烷基（芳基）-4-四甲基亚磺酰亚胺-1,1,1-三氟烷基-3-烯-2-酮，收率良好。随后，本研究还报道了利用 t-丁醇钾在二乙醚中于回流条件下进行的亚磺酰亚胺烯酮分子内环化反应，轻松制备出一系列新的融合杂环体系 3-芳基-5-三氟甲基-7,8-二氢-6H-噻吩并[2,1-f][1,2]噻嗪 1-氧化物衍生物（产率为 60- 85%）。
• New trifluoromethyl-containing (E)-N′-arylidene-[3-alkyl(aryl/heteroaryl)-4,5-dihydro-1H-pyrazol-1-yl]carbohydrazides: Synthesis, crystal structure and antimicrobial/antioxidant activity
  作者：Helio G. Bonacorso、Susiane Cavinatto、Patrick T. Campos、Liliane M.F. Porte、Jussara Navarini、Gisele R. Paim、Marcos A.P. Martins、Nilo Zanatta、Caroline Z. Stuker

  DOI：10.1016/j.jfluchem.2011.12.010

  日期：2012.3

  A new series of twenty-one trifluoromethyl-containing (E)-N'-arylidene-1H-pyrazole-1-carbohydrazides (4) was synthesized by the cyclocondensation reactions of six 3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazole-1-carbohydrazides (2) with eleven aryl/heteroaryl aldehydes and acetophenone (3) in 52-97% yields and six new carbohydrazides 2 were easily obtained from the reaction of 1,1,1-trifluoro-4-alkyl(aryl/heteroaryl)-4-methoxy-3-alken-2-ones (1) with carbohydrazide. Subsequently, four examples of carbohydrazides 4 were fully studied by X-ray diffraction and the twenty-seven pyrazolyl-carbohydrazides 2 and 4 screened for their antioxidant and antimicrobial proprieties and evaluated by DPPH and MIC methods, respectively. Both series 2 and 4 showed ability to capture DPPH free radical for IC50 from 47.57 to 487 mu g/mL. Most of the compounds presented fungistatic and bacteriostatic activity only for high MIC levels ranging from 0.25 mg/mL to 0.5 mg/mL. (C) 2011 Elsevier B.V. All rights reserved.
• The first application of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones in a three-component condensation protocol for the synthesis of 3-acyl-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones
  作者：Helio G. Bonacorso、Jussara Navarini、Carson W. Wiethan、Guilherme P. Bortolotto、Gisele R. Paim、Susiane Cavinatto、Marcos A.P. Martins、Nilo Zanatta、Miguel S.B. Caro

  DOI：10.1016/j.jfluchem.2010.12.011

  日期：2011.3

  The one-pot, simple and efficient three-component condensation protocol for the preparation of a series of twenty-five new 3-acy1-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7.8-tetrahydro-2H-chromen-5(6H)-ones, where aryl = Ph, 4-tolyl, 4-CIPh, 4-NO2Ph and 4-CHOPh, and acyl = Ac, Bz, 4-FBz, furan-2-oyl, thien-2-oyl and naphth-1-oyl, employing 1,3-cyclohexanedione, five aryl aldehydes and for the first time, six 4-alkyl(aryl/heteroaryl)-4-methoxy-1,1,1-trifluoroalk-3-en-2-ones, is described. Yields in 15-75% were obtained when the MCRs were performed in the presence of a catalytic amount of triethylamine (25 mol%) and in ethanol as solvent under reflux for 16 h. A representative X-ray diffraction data for 3-acetyl-4-phenyl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one is also showed. (C) 2010 Elsevier B.V. All rights reserved.
• One‐pot synthesis of <i>N</i> ² ‐aminoprotected 6‐substituted and cycloalka[ <i>d</i> ] 4‐trifluoromethyl‐2‐acetylaminopyrimidines
  作者：Helio G. Bonacorso、Adriana Ferla、Cleber A. Cechinel、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.1002/jhet.5570450228

  日期：2008.3

  Abstractmagnified imageThe one‐pot synthesis of a novel series of amino‐protected 6‐alkyl‐, 6‐aryl‐, 6‐heteroaryl‐ and 5,6‐fused‐cycloalkane 4‐trifluoromethyl‐2‐acetylaminopyrimidines, where alkyl = Me; aryl = Ph, 4‐CH3Ph, 4‐FPh, 4‐ClPh, 4‐BrPh, 4‐OCH3Ph, 4‐NO2Ph, 4,4′‐biphenyl, 1‐naphthyl; heteroaryl = 2‐thienyl, 2‐furyl and cycloalkyl = c‐C6H4, c‐C7H5 from the reaction of substituted 4‐methoxy‐1,1,1‐trifluoroalk‐3‐en‐2‐ones with 1‐acetylguanidine in acetonitrile or propan‐2‐ol as solvent, is reported. The acetylamino group of 2‐acetylaminopyrimidines was hydrolyzed under three different conditions to afford the corresponding free 2‐aminopyrimidines.