(Z)-2,3-Dihydro-3-<(4-chlorophenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one | 112014-59-2

• 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-chlorophenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one
• 英文别名: (3Z)-3-[(4-chlorophenyl)methylidene]-2-phenylchromen-4-one
• CAS: 112014-59-2
• 化学式: C₂₂H₁₅ClO₂
• 分子量: 346.813
• InChiKey: GKLOKWXEPRNITG-XMHGGMMESA-N

物化性质

• 沸点：
  533.8±50.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2,3-Dihydro-3-<(4-chlorophenyl)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 432.0h， 以15%的产率得到3-(4-Chlorobenzoyl)-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-chlorophenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one 在 phase transfer 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-2,3-Dihydro-3-<(4-chlorophenyl)methylene>-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

• Flavanoids. Part 6. The kinetics and mechanism of base-catalysed isomerisation of 3-arylideneflavanones
  作者：Dilip Dattatraya Dhavale、Poonam Joshi、Keshav Gangadhar Marathe

  DOI：10.1039/p29870000449

  日期：——

  Base-catalysed Z→E conversion of 3-arylideneflavanones provide a unique system suitable for kinetic studies by 1H n.m.r. spectroscopy. Isomerisation studies of 10 enones in [2H5] pyridine showed that a first-order unimolecular reaction was taking place. The Hammett σ–ρ relationship is not adequate to accommodate the substituent effect on rate in the case of p- and m-nitro-3-benzylidene derivatives

  3-芳基黄烷酮的碱催化Z → E转化提供了一个适用于1 H nmr光谱动力学研究的独特系统。在[ 2 H 5 ]吡啶中对10个烯酮进行异构化研究表明，正在发生一阶单分子反应。哈米特σ-ρ关系不足以适应的情况下，上速率的取代基影响p -和米硝基-3-亚苄基衍生物。讨论了硝基取代基的异常情况。
• Structure–cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones
  作者：Bogumiła Kupcewicz、Grażyna Balcerowska-Czerniak、Magdalena Małecka、Piotr Paneth、Urszula Krajewska、Marek Rozalski

  DOI：10.1016/j.bmcl.2013.05.044

  日期：2013.7

  The E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone derivatives were tested in vitro for their cytotoxic activity against three cancer cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC). It was observed that substitution at C-3 position led to significant enhance in cytotoxicity. Isomeric configuration of 3-arylideneflavanones had an influence on the cytotoxic potential. Multiple regression analysis combined with variable selection by genetic algorithm was used to model relationships between molecular descriptors and the cytotoxic activity. The most accurate QSAR models were based on a combination between energy of LUMO, experimental value of logP and partial charge on carbonyl oxygen (delta O-2). (C) 2013 Elsevier Ltd. All rights reserved.
• 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：——