2-benzoyl-3-(4-bromophenyl)-6,6-dimethyl-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-3-(4-bromophenyl)-6,6-dimethyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
• 英文别名: 2-benzoyl-3-(4-bromophenyl)-3,5,6,7-tetrahydro-6,6-dimethyl-1-benzofuran-4(2H)-one；(2S,3S)-2-benzoyl-3-(4-bromophenyl)-6,6-dimethyl-2,3,5,7-tetrahydro-1-benzofuran-4-one
• 化学式: C₂₃H₂₁BrO₃
• 分子量: 425.322
• InChiKey: QGPZXFDVAVTSAI-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1-phenyl-2-(p-tolylsulfonyloxy)ethanone 、 5,5-二甲基-1,3-环己二酮 、 对溴苯甲醛 在 2,3-二氮杂萘 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以86%的产率得到2-benzoyl-3-(4-bromophenyl)-6,6-dimethyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one
  参考文献：
  名称：

  2,3-二氢呋喃作为潜在的细胞毒性和抗菌剂：使用 α-甲苯磺酰氧基酮前体合成 2,3-二氢呋喃的串联 Knoevenagel Michael 环化

  摘要：

  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。

  DOI：

  10.1002/cbdv.201800277

文献信息

• 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.
• 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。