3-(4-Chlorobenzoyl)-2-phenyl-4H-1-benzopyran-4-one | 65485-14-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-(4-Chlorobenzoyl)-2-phenyl-4H-1-benzopyran-4-one
• 英文别名: 3-[(4-chlorophenyl)carbonyl]-2-phenyl-4H-chromen-4-one；3-(4-chloro-benzoyl)-2-phenyl-chromen-4-one；3-(4-Chlorobenzoyl)-2-phenylchromen-4-one
• CAS: 65485-14-5
• 化学式: C₂₂H₁₃ClO₃
• 分子量: 360.796
• InChiKey: IPXFLMZFGVQWMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153 °C
• 沸点：
  516.1±50.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4''-chloro-3-α-hydroxybenzylflavone 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到3-(4-Chlorobenzoyl)-2-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Flavanoid part 71: A novel photosynthesis of 3α-hydroxybenzylflavones from 3-arylideneflavanones

  摘要：

  DOI：

  10.1016/s0040-4020(88)90041-5

文献信息

• A concise synthesis of 3-aroylflavones via Lewis base 9-azajulolidine-catalyzed tandem acyl transfer–cyclization
  作者：Masahito Yoshida、Koya Saito、Yuta Fujino、Takayuki Doi

  DOI：10.1039/c2cc37015h

  日期：——

  Lewis base-catalyzed tandem acyl transfer-cyclization of acylated o-alkynoylphenols leading to 3-aroylflavones was developed. 9-Azajulolidine smoothly promoted the reaction of the aroyl derivatives at ambient temperature, and the structure-diversed synthesis of 3-aroylflavones with distinct substituents was achieved in moderate to excellent yields.

  开发了路易斯碱催化导致3-芳基黄酮的酰化的邻炔基酚的串联酰基转移环化。9-氮杂唑烷在环境温度下平稳地促进了芳酰基衍生物的反应，并且以中等至优异的产率实现了具有不同取代基的3-芳酰基黄酮的结构多样的合成。
• Transition-Metal-Free Synthesis of 3-Acyl Chromones by the Tandem Reaction of Ynones and Methyl Salicylates
  作者：Ya-Fang Ye、Feng Li、Jia-Le Chen、Zi-Qian An、Gui-Ying Zhang、Yan-Bo Wang

  DOI：10.1021/acs.joc.2c01637

  日期：2022.11.4

  effective tandem reaction of ynones and methyl salicylates was developed to obtain a broad range of 3-acyl chromones in moderate-to-excellent yields. This protocol underwent a Michael addition and cyclization process, which exhibited easily accessible substrates, broad substrate scope, and high regioselectivity under mild and transition-metal-free conditions. Moreover, gram-scale reaction and further chemical

  开发了 ynones 和水杨酸甲酯的简单有效的串联反应，以获得范围广泛的 3-酰基色酮，收率中等至极佳。该协议经历了迈克尔加成和环化过程，在温和和无过渡金属的条件下表现出易于获得的底物、广泛的底物范围和高区域选择性。此外，还进一步研究了产物的克级反应和进一步的化学转化。
• 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.
• DHANDE, V. P.;THAKWANI, POONAM;MARATHE, K. G., TETRAHEDRON, 44,(1988) N 10, 3015-3023
  作者：DHANDE, V. P.、THAKWANI, POONAM、MARATHE, K. G.

  DOI：——

  日期：——