3-benzoyl-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one | 1313223-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one
• 英文别名: 3-Benzoyl-4-phenyl-2-(trifluoromethyl)-2-hydroxy-2,3,4,6,7,8-hexahydro-5H-1-benzopyran-5-one；3-benzoyl-2-hydroxy-4-phenyl-2-(trifluoromethyl)-4,6,7,8-tetrahydro-3H-chromen-5-one
• CAS: 1313223-81-2
• 化学式: C₂₃H₁₉F₃O₄
• 分子量: 416.397
• InChiKey: YFNVOVQTNNIWGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one 在 二甲氨基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到3-benzoyl-2-fluoro-4-phenyl-2-(trifluoromethyl)-4,6,7,8-tetrahydro-3H-chromen-5-one
  参考文献：
  名称：

  Chemoselective fluorination of 2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones using DAST

  摘要：

  In this study, diethylaminosulfur trifluoride (DAST) was successfully applied in monofluorination reactions of some trifluoromethyl substituted 2-hydroxy-2H-chromenones, employing a general, mild, and efficient methodology. The fluorinated compounds (2-fluoro-2H-chromenones) were synthesized as unique products by a chemoselective reaction in 63-81% yield despite the presence of different reactive sites subjected to reactions with DAST. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.070
• 作为产物：
  描述：

  (1,1-二甲氧基乙基)苯 在 吡啶 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 3-benzoyl-2-hydroxy-4-phenyl-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2010.12.011

文献信息

• ANRORC rearrangement in tetrahydro-2H-chromenones. Synthesis and structural assignment by NMR, MS, X-ray and DFT calculations of 2-[3(5)-trifluoromethyl-1H-pyrazol-4-yl)arylmethyl]cyclohexenones and derivatives
  作者：Helio G. Bonacorso、Jussara Navarini、Liliane M.F. Porte、Everton P. Pittaluga、Andrizia F. Junges、Alexandre R. Meyer、Marcos A.P. Martins、Nilo Zanatta

  DOI：10.1016/j.jfluchem.2013.03.014

  日期：2013.7

  chloride easily converted a pyrazole like 2 to its N-benzyl derivative (4), at 69% yield. Finally, the structural assignment of compounds 2–4 was deduced by mass spectrometry, X-ray crystal diffraction and density functional theory (DFT) calculations, which clearly and unambiguously furnished values very close to those determined from 1H, 13C and 19F NMR data.

  本文首先描述了一种新系列3-羟基-2的合成- [（3（5） - （甲基/苯基）-5（3） - （三氟甲基）-1 ħ吡唑-4-基）芳甲基]环己-2-烯-1-酮（2），其中芳基= C 6 H ^ 5，4-NO 2 C ^ 6 ħ 4，4-OCH 3 C ^ 6 ħ 4，从3-酰基的ANRORC环转化反应-4-芳基-2-（三氟甲基）-2-羟基-3,4,7,8-四氢-2- ħ -苯并吡喃5（6 ħ）-一（1），在水合肼存在下，酰基=乙酰基和苯甲酰基，产率63-90％。在随后的步骤，从2-氧化芳构化反应在碘/甲醇介质做了的3（5）三氟甲基- 5（3） -甲基- 4的制备- [（2,6-二甲氧基苯基） - （4-甲氧基苯基甲基）] - 1 H ^吡唑（3）在72％的产率。此外，使用苄基氯烷基化反应容易地转化的吡唑类2以它的Ñ -苄基衍生物（4）中，在69％收率。最后，化合物2-4的结构分配通过质谱法，
• Efficient entry to trifluoromethyl substituted chromanes from oxidative aromatization of tetrahydro-2H-chromen-5(6H)-ones using iodine/alcohol with conventional and microwave methods
  作者：Helio G. Bonacorso、Jussara Navarini、Carson W. Wiethan、Andrizia F. Junges、Susiane Cavinatto、Rosália Andrighetto、Marcos A.P. Martins、Nilo Zanatta

  DOI：10.1016/j.jfluchem.2012.06.024

  日期：2012.10

  This paper describes the one-pot simple and efficient oxidative aromatization reaction employing an iodine/alcohol medium for the preparation of a series of 11 new 3-acyl-2-hydroxy-5-alkoxy-4-aryl-2-(trifluoromethyl)chromanes, where acyl = Ac, Bz, furan-2-oyl; aryl = Ph, 4-NO2C6H4, 4-OCH3C6H4 and alkoxy = OMe, O-Pr-n, EtO and OBn from the respective 3-acyl-4-aryl-2-(trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones. Yields in the range of 50-89% were obtained when the oxidative reactions were performed using both conventional thermal heating (CTH) and microwave (MW) procedures. In general, the MW method produced similar yields with shorter reaction times and easier reaction workups. As an example, a representative X-ray diffraction ORTEP for 3-benzoyl-2-hydroxy-5-methoxy-4-methoxyphenyl-2-(trifluoromethyl)chromane is also shown. (C) 2012 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.
• Chemoselective fluorination of 2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones using DAST
  作者：Helio G. Bonacorso、Liliane M.F. Porte、Jussara Navarini、Gisele R. Paim、Fábio M. Luz、Lenon M. Oliveira、Carson W. Whietan、Marcos A.P. Martins、Nilo Zanatta

  DOI：10.1016/j.tetlet.2011.04.070

  日期：2011.6

  In this study, diethylaminosulfur trifluoride (DAST) was successfully applied in monofluorination reactions of some trifluoromethyl substituted 2-hydroxy-2H-chromenones, employing a general, mild, and efficient methodology. The fluorinated compounds (2-fluoro-2H-chromenones) were synthesized as unique products by a chemoselective reaction in 63-81% yield despite the presence of different reactive sites subjected to reactions with DAST. (C) 2011 Elsevier Ltd. All rights reserved.