5,7-二甲氧基-8-甲基-2-苯基色烯-4-酮 | 14004-47-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5,7-二甲氧基-8-甲基-2-苯基色烯-4-酮
• 英文名称: 5,7-dimethoxy-8-methyl-2-phenylchromen-4-one
• 英文别名: 5,7-dimethoxy-8-methylflavone；5,7-dimethoxy-8-methyl-2-phenyl-chromen-4-one；5,7-Dimethoxy-8-methyl-2-phenyl-chromen-4-on；8-Methyl-chrysin-dimethylether；5,7-Dimethoxy-8-methyl-flavon；Cryptochrysin, Di-methyl ether
• CAS: 14004-47-8
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: AAZUHFASGMBVSG-UHFFFAOYSA-N

物化性质

• 熔点：
  231-232 °C(Solv: ethanol (64-17-5))
• 沸点：
  488.7±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-二甲氧基-8-甲基-2-苯基色烯-4-酮 在 吡啶盐酸盐 作用下， 生成 5-羟基-7-甲氧基-8-甲基-2-苯基色烯-4-酮
  参考文献：
  名称：

  Lindstedt; Misiorny, Acta Chemica Scandinavica (1947), 1951, vol. 5, p. 1,3

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三甲氧基甲苯 在 四氢吡咯 、 manganese(IV) oxide 、 三氯化铝 、 lithium diisopropyl amide 、 三氯氧磷 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 109.0h， 生成 5,7-二甲氧基-8-甲基-2-苯基色烯-4-酮
  参考文献：
  名称：

  Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone

  摘要：

  The synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone is described. A new chromylation method of beta-ketosulfoxide 9 leading to the Michael acceptor 12 has been developed. Dilithium tetrachlorocuprate was shown to be a very efficient catalyst for the conjugate addition reaction of phenyl magnesium bromide to the alpha,beta-unsaturated sulfoxide 12. The instability of the obtained adducts 10 represents a limitation in terms of yield. It was confirmed that the natural flavanone leridol does not possess the structure of title compound 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00266-9

文献信息

• Mukerjee; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 38, p. 207,217
  作者：Mukerjee、Seshadri

  DOI：——

  日期：——
• A chrysin analog exhibited strong inhibitory activities against both PGE2 and NO production
  作者：Haiyan Che、Hyun Lim、Hyun Pyo Kim、Haeil Park

  DOI：10.1016/j.ejmech.2011.04.044

  日期：2011.9

  A number of 8-substituted chrysin analogs have been prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin E-2 and iNOS-mediated NO production. Analogs were prepared via Suzuki-Miyaura C-C cross coupling reaction of 8-iodo-5,7-dimethoxyflavone and alkyl/areneboronic acids as a key reaction. Among the analogs tested, 5,7-dihydroxy-8-(pyridine-4-yl) flavone (3d) showed strong biological activities against COX-2 catalyzed PGE(2) and iNOS-mediated NO production from LPS-induced RAW 264.7 cells compared to those of chrysin. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Anti-AIDS agents 68. The first total synthesis of a unique potent anti-HIV chalcone from genus Desmos
  作者：Kyoko Nakagawa-Goto、Kuo-Hsiung Lee

  DOI：10.1016/j.tetlet.2006.09.110

  日期：2006.11

  The first total synthesis of a unique highly functionalized and potent anti-HIV chalcone 1, isolated from genus Desmos, was achieved from commercially available 2,4,6-trihydroxytoluene (3) or 2,4,6-trihydroxybenzaldehyde (2) in five (from 3) or six steps (from 2). (c) 2006 Elsevier Ltd. All rights reserved.
• A Facile Baker-Venkataraman Synthesis of Flavones using Phase Transfer Catalysis
  作者：P. K. Jain、J. K. Makrandi、S. K. Grover

  DOI：10.1055/s-1982-29755

  日期：——
• Matsuura, Pharmaceutical Bulletin, 1957, vol. 5, p. 195,197
  作者：Matsuura

  DOI：——

  日期：——