(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-propan-2-ylhepta-1,6-diene-3,5-dione | 98885-97-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-propan-2-ylhepta-1,6-diene-3,5-dione
• CAS: 98885-97-3
• 化学式: C₂₄H₂₆O₆
• 分子量: 410.467
• InChiKey: KYBHXIOHBNXNGN-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-ethylidene-pentane-2,4-dione 在 boron trioxide 、 硼酸三丁酯 、 正丁胺 作用下， 以 乙醚 为溶剂， 反应 25.0h， 生成 (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-propan-2-ylhepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Pedersen, Uffe; Rasmussen, Preben B.; Lawesson, Sven-Olov, Liebigs Annalen der Chemie, 1985, # 8, p. 1557 - 1569

  摘要：

  DOI：

文献信息

• Electron ionization mass spectrometry of curcumin analogues: an olefin metathesis reaction in the fragmentation of radical cations
  作者：Ben L. M. van Baar、Jelle Rozendal、Henk van der Goot

  DOI：10.1002/(sici)1096-9888(199804)33:4<319::aid-jms636>3.0.co;2-u

  日期：1998.4

  The natural compound curcumin, used in cosmetics, traditional medicines and as a spice in food, is known as a multi-factorial anti-inflammatory agent. To study the anti-inflammatory activity of curcumin derivatives, 24 analogues were synthesized and their structures were confirmed by H-1 MMR and electron ionization (EI) mass spectrometry. Most signals in the EI mass spectra can be attributed to commonly known fragmentations, but the formation of ring-substituted 1,2-diphenylethene (stilbene)-type radical cations, observed in the spectra of all compounds investigated and resulting in the base peak for some compounds, requires a peculiar rearrangement. Metastable ion spectra and C-13 labelling studies show that the stilbene-type ions are formed directly from the molecular ions and contain the two original aryl groups and the 1 and 7 carbon atoms of the olefinic system. It is proposed that the formation of stilbene-type ions results from an intramolecular olefin metathesis reaction; this suggestion is supported by semi-empirical (MNDO/PM3) calculations. (C) 1998 John Wiley & Sons, Ltd.