(Z)-2,3-Dihydro-3-<(4-ethoxyphenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (Z)-2,3-Dihydro-3-<(4-ethoxyphenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one
• 英文别名: 3-(4-ethoxybenzylidene)-2-phenyl-2,3-dihydro-4H-chromen-4-one；(3Z)-3-[(4-ethoxyphenyl)methylidene]-2-phenylchromen-4-one
• 化学式: C₂₄H₂₀O₃
• 分子量: 356.421
• InChiKey: KLQSFWNYUJSBCY-LTGZKZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2,3-Dihydro-3-<(4-ethoxyphenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 336.0h， 以14%的产率得到trans-2,3-Dihydro-3-(ethoxybenzoyl)-2-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Dioxirane Oxidation of 3-Arylideneflavanones: Diastereoselective Formation of trans,trans Spiroepoxides from the E Isomers

  摘要：

  Oxidation of the E isomers of the 3-arylideneflavanones 1 by dimethyldioxirane in acetone solution at ambient temperature led to spiroepoxides trans,trans-2 in high yields (greater than or equal to 170%) and complete diastereoselectivity. Steric interaction with the axial aryl group in the 3-arylideneflavanone E-1. directs the attack of the dioxirane to the opposite side during the oxygen transfer to afford exclusively the trans,trans-2 epoxides, which clearly demonstrates the advantage of dimethyldioxirane as oxidant. In comparison, these substrates give under Weitz-Scheffer conditions (alkaline hydrogen peroxide) both diastereomeric epoxides (dr ca. 3:1) in poor yields (less than or equal to 130%), while m-CPBA produces trans,trans-2 spiroepoxides preferentially, but also in low yields (less than or equal to 140%).(1,2) Attempted epoxidation of the Z isomers afforded instead the 3-benzoylflavones 3 and/or 3-benzoylflavanones 4 in low yields. With the much more reactive methyl(trifluoromethyl)dioxirane, the E-1 isomers also gave the trans,-trans-2 spiroepoxides diastereoselectively in high yields, but the Z isomers suffered complete decomposition. Presumably the sterically hindered Z isomers encumber the oxygen atom transfer by the dioxirane and radical-type oxidation dominates for these reluctant substrates.

  DOI：

  10.1021/jo00083a035
• 作为产物：
  描述：

  (E)-2,3-Dihydro-3-<(4-ethoxyphenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one 以 苯 为溶剂， 反应 20.0h， 以38%的产率得到(Z)-2,3-Dihydro-3-<(4-ethoxyphenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Dioxirane Oxidation of 3-Arylideneflavanones: Diastereoselective Formation of trans,trans Spiroepoxides from the E Isomers

  摘要：

  Oxidation of the E isomers of the 3-arylideneflavanones 1 by dimethyldioxirane in acetone solution at ambient temperature led to spiroepoxides trans,trans-2 in high yields (greater than or equal to 170%) and complete diastereoselectivity. Steric interaction with the axial aryl group in the 3-arylideneflavanone E-1. directs the attack of the dioxirane to the opposite side during the oxygen transfer to afford exclusively the trans,trans-2 epoxides, which clearly demonstrates the advantage of dimethyldioxirane as oxidant. In comparison, these substrates give under Weitz-Scheffer conditions (alkaline hydrogen peroxide) both diastereomeric epoxides (dr ca. 3:1) in poor yields (less than or equal to 130%), while m-CPBA produces trans,trans-2 spiroepoxides preferentially, but also in low yields (less than or equal to 140%).(1,2) Attempted epoxidation of the Z isomers afforded instead the 3-benzoylflavones 3 and/or 3-benzoylflavanones 4 in low yields. With the much more reactive methyl(trifluoromethyl)dioxirane, the E-1 isomers also gave the trans,-trans-2 spiroepoxides diastereoselectively in high yields, but the Z isomers suffered complete decomposition. Presumably the sterically hindered Z isomers encumber the oxygen atom transfer by the dioxirane and radical-type oxidation dominates for these reluctant substrates.

  DOI：

  10.1021/jo00083a035

文献信息

• Dioxirane Oxidation of 3-Arylideneflavanones: Diastereoselective Formation of trans,trans Spiroepoxides from the E Isomers
  作者：Csaba Nemes、Albert Levai、Tamas Patonay、Gabor Toth、Sandor Boros、Judit Halasz、Waldemar Adam、Dieter Golsch

  DOI：10.1021/jo00083a035

  日期：1994.2

  Oxidation of the E isomers of the 3-arylideneflavanones 1 by dimethyldioxirane in acetone solution at ambient temperature led to spiroepoxides trans,trans-2 in high yields (greater than or equal to 170%) and complete diastereoselectivity. Steric interaction with the axial aryl group in the 3-arylideneflavanone E-1. directs the attack of the dioxirane to the opposite side during the oxygen transfer to afford exclusively the trans,trans-2 epoxides, which clearly demonstrates the advantage of dimethyldioxirane as oxidant. In comparison, these substrates give under Weitz-Scheffer conditions (alkaline hydrogen peroxide) both diastereomeric epoxides (dr ca. 3:1) in poor yields (less than or equal to 130%), while m-CPBA produces trans,trans-2 spiroepoxides preferentially, but also in low yields (less than or equal to 140%).(1,2) Attempted epoxidation of the Z isomers afforded instead the 3-benzoylflavones 3 and/or 3-benzoylflavanones 4 in low yields. With the much more reactive methyl(trifluoromethyl)dioxirane, the E-1 isomers also gave the trans,-trans-2 spiroepoxides diastereoselectively in high yields, but the Z isomers suffered complete decomposition. Presumably the sterically hindered Z isomers encumber the oxygen atom transfer by the dioxirane and radical-type oxidation dominates for these reluctant substrates.