2-benzoyl-6,6-dimethyl-3-(4-tolyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyl-6,6-dimethyl-3-(4-tolyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
• 英文别名: 2-benzoyl-3,5,6,7-tetrahydro-6,6-dimethyl-3-(4-methylphenyl)-1-benzofuran-4(2H)-one；6,6-dimethyl-2-benzoyl-3-(p-methylphenyl)-3,5,6,7-tetrahydro-2H-benzofuran-4-one；(+/-)-trans-2-benzoyl-6,6-dimethyl-3-(4-methylphenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；(2S,3S)-2-benzoyl-6,6-dimethyl-3-(4-methylphenyl)-2,3,5,7-tetrahydro-1-benzofuran-4-one
• 化学式: C₂₄H₂₄O₃
• 分子量: 360.453
• InChiKey: QFLQYCQMRQCBEB-REWPJTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 、 5,5-二甲基-1,3-环己二酮 在 ammonium cerium (IV) nitrate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 25.5h， 以80%的产率得到2-benzoyl-6,6-dimethyl-3-(4-tolyl)-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
  参考文献：
  名称：

  CAN-promoted, diastereoselective synthesis of fused 2,3-dihydrofurans and their transformation into tetrahydroindoles

  摘要：

  The reaction between 1 3-cyclohexanediones and chalcones (or their vinilogs) in the presence of 2 5 equiv of cerium(IV) ammonium nitrate afforded trans-2-arylcarbonyl-3-aryl (or styryl)-2 3 6 7-tetrahydrobenzofuran-4(5H)-ones in good to excellent yields and in high diastereoselectivities The method was also extended to the preparation of derivatives of the 5 6-dihydro-2H-cyclopenta[b]furan-4(3H)-one system The fused 2 3-dihydrofuran derivatives were transformed into 1-alkyl-2-acyl-3-aryl-6 7-dihydroindole-4(5H)-ones by 2 3-dehydrogenation followed by reaction with primary amines The direct reaction of the tetrahydrobenzofuran-4(5H)-one compounds derived from dimedone with amines gave 1-alkyl-2-alkylimino-3-aryl-6 7-dihydroindole-4(5H)-ones while starting materials derived from 1 3-cyclohexanedione underwent an unprecedented 2-deacylation reaction and gave 1-alkyl-3-aryl-6 7-dihydroindole-4(5H)-ones (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.10.017

文献信息

• 2,3-Dihydrofurans as Potential Cytotoxic and Antibacterial Agents: Tandem Knoevenagel−Michael Cyclization for the Synthesis of 2,3-Dihydrofurans by Using α-Tosyloxy Ketone Precursors
  作者：Jajula Kashanna、Rathod Aravind Kumar、Ravada Kishore、Duddukuri Nandan Kumar、Alleni Suman Kumar

  DOI：10.1002/cbdv.201800277

  日期：2018.11

  Novel 2,3‐dihydrofuran derivatives were synthesized through a tandem Knoevenagel−Michael cyclization in good yield by reacting α‐tosyloxy ketone, 5,5‐dimethyl‐1,3‐cyclohexanedione, and various aldehydes in the presence of phthalazine in acetonitrile. These compounds were subjected to in vitro antibacterial screening against eight micro‐organisms by using diffusion method and also in vitro cytotoxicity

  α-甲苯磺酰氧基酮、5,5-二甲基-1,3-环己二酮和各种醛在乙腈中存在酞嗪的情况下，通过串联 Knoevenagel-Michael 环化反应合成了新型 2,3-二氢呋喃衍生物。使用扩散法对这些化合物进行了针对八种微生物的体外抗菌筛选，并通过应用 MTT 法对四种人癌细胞系进行了体外细胞毒性筛选。一些化合物显示出令人印象深刻的活性。
• Diastereoselective Synthesis of <i>trans</i>-2,3-Dihydrofurans with Pyridinium Ylide Assisted Tandem Reaction
  作者：Qi-Fang Wang、Hong Hou、Li Hui、Chao-Guo Yan

  DOI：10.1021/jo901379h

  日期：2009.10.2

  An efficient synthetic procedure for the preparation of fused 2,3-dihydrofuran derivatives was developed with the assistance of pyridinium ylide. A sequential one-pot, two-step tandem reaction starting from pyridine, aromatic aldehyde, dimedone, or 4-hydroxycoumarin and alpha-phenacyl bromide or p-nitrobenzyl bromide with triethylamine as catalyst proceeded smoothly in acetonitrile. H-1 NMR spectroscopy and single-crystal analysis demonstrated that the obtained 2,3-dihydrofurans are trans isomers.
• Regio- and Diastereoselective Synthesis of trans-2,3-Dihydrofuran Derivatives in an Aqueous Medium
  作者：Abu Khan、Mohan Lal、R. Sidick Basha

  DOI：10.1055/s-0032-1316837

  日期：——

  A wide variety of fused trans-2,3-dihydrofuran derivatives were synthesized through a one-pot three-component reaction of an aromatic aldehyde, a cyclic beta-diketo compound, and an in situ-generated pyridinium ylide in refluxing. The pyridinium ylide was formed from either 2-bromo-1-phenylethanone or 4-nitrobenzyl bromide and pyridine in the presence of 10 mol% of sodium hydroxide. Pyridine plays crucial role in forming the pyridinium salt, which, in turn, forms a nitrogen ylide in the presence of sodium hydroxide. The ylide assists a Michael-initiated ring-closure reaction, but is not itself incorporated in the final product. The protocol is environmentally acceptable because no organic solvent is involved at any stage. Furthermore, the method is highly diastereoselective, gives good yields, and does not involve extensive workup procedures or chromatographic separations, as the desired products can be isolated by filtration and drying.
• CAN-promoted, diastereoselective synthesis of fused 2,3-dihydrofurans and their transformation into tetrahydroindoles
  作者：Swarupananda Maiti、Paramasivan T. Perumal、J. Carlos Menéndez

  DOI：10.1016/j.tet.2010.10.017

  日期：2010.12

  The reaction between 1 3-cyclohexanediones and chalcones (or their vinilogs) in the presence of 2 5 equiv of cerium(IV) ammonium nitrate afforded trans-2-arylcarbonyl-3-aryl (or styryl)-2 3 6 7-tetrahydrobenzofuran-4(5H)-ones in good to excellent yields and in high diastereoselectivities The method was also extended to the preparation of derivatives of the 5 6-dihydro-2H-cyclopenta[b]furan-4(3H)-one system The fused 2 3-dihydrofuran derivatives were transformed into 1-alkyl-2-acyl-3-aryl-6 7-dihydroindole-4(5H)-ones by 2 3-dehydrogenation followed by reaction with primary amines The direct reaction of the tetrahydrobenzofuran-4(5H)-one compounds derived from dimedone with amines gave 1-alkyl-2-alkylimino-3-aryl-6 7-dihydroindole-4(5H)-ones while starting materials derived from 1 3-cyclohexanedione underwent an unprecedented 2-deacylation reaction and gave 1-alkyl-3-aryl-6 7-dihydroindole-4(5H)-ones (C) 2010 Elsevier Ltd All rights reserved