(E)-α-methyl-2-styrylchromone | 143583-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-α-methyl-2-styrylchromone
• 英文别名: 2-[(E)-1-phenylprop-1-en-2-yl]chromen-4-one
• CAS: 143583-47-5
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: YAPYGARUFVRIHX-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-α-methyl-2-styrylchromone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 22.0h， 生成 2-(2-Methyl-3-phenyl-1,2-dihydro-naphthalen-2-yl)-chromen-4-one
  参考文献：
  名称：

  Silva, Artur M. S.; Silva, Ana M. G.; Tome, Augusto C., European Journal of Organic Chemistry, 1999, # 1, p. 135 - 139

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E,4E)-1-(2-hydroxyphenyl)-4-methyl-5-phenylpenta-2,4-dien-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以11%的产率得到(Z)-α-methyl-2-styrylchromone
  参考文献：
  名称：

  Silva, Artur M. S.; Pinto, Diana C. G. A.; Tavares, Hilario R., European Journal of Organic Chemistry, 1998, # 9, p. 2031 - 2038

  摘要：

  DOI：

文献信息

• A new xanthone synthesis from the Diels–Alder reaction between 2-vinylchromen-4-ones and cyclopentanone enamine
  作者：Roy M. Letcher、Tai-Yuen Yue

  DOI：10.1039/c39920001310

  日期：——

  The reaction between 2-vinylchromen-4-ones and 1-pyrrolidinylcyclopentene give substituted 2,3,3a,4-tetrahydrocyclopenta[a]xanthen-11(5H)-ones; the stereochemistry of the product shows that the initial step in the reaction may be considered to be an exo-addition Diels–Alder with inverse electron demand.

  2-vinylchromen-4-ones 和 1-pyrrolidinylcyclopentene 反应生成了取代的 2,3,3a,4-tetrahydrocyclopenta[a]xanthen-11(5H)-ones；产物的立体化学性质表明，反应的第一步可视为具有反电子需求的外加 DielsâAlder。
• (E)-2-Styrylchromones as potential anti-norovirus agents
  作者：Joana Rocha-Pereira、Ricardo Cunha、Diana C.G.A. Pinto、Artur M.S. Silva、Maria São José Nascimento

  DOI：10.1016/j.bmc.2010.05.006

  日期：2010.6.15

  Human noroviruses (NoV) are now recognized as the most frequent cause of outbreaks and sporadic cases of acute gastroenteritis. Despite the significant economic impact and considerable morbidity of norovirus disease, no drug or vaccine is currently available to treat or prevent this disease, therefore the discovery of anti-norovirus drugs is urgent.In the present work, a total of 12 structure related chromone and (E)-2-styrylchromones were evaluated for their potential anti-norovirus activity using the murine norovirus (MNV) as a surrogate model for human NoV.From the 12 compounds studied, six (E)-2-styrylchromones were found to have with interesting antinorovirus activity. The best compounds of the series were (E)-5-hydroxy-2-styrylchromone and (E)-4'-methoxy-2-styrylchromone with an IC50 approximate to 7 mu M. A first insight into the mechanism of action of these compounds was possible. An interesting relationship between the anti-norovirus activity and the chemical structure was observed. The present study points out that the (E)-2-styrylchromones skeleton is an important one which deserves to be developed and further explored as new antiviral drugs against NoV. (C) 2010 Elsevier Ltd. All rights reserved.
• Letcher Roy M., Yue Tai-Yuen, J. Chem. Soc. Chem. Commun., (1992) N 18, S 1310-1311
  作者：Letcher Roy M., Yue Tai-Yuen

  DOI：——

  日期：——
• Letcher, Roy M.; Yue, Tai-Yuen, Journal of Chemical Research, Miniprint, 1992, p. 2078 - 2089
  作者：Letcher, Roy M.、Yue, Tai-Yuen

  DOI：——

  日期：——
• Silva, Artur M. S.; Pinto, Diana C. G. A.; Tavares, Hilario R., European Journal of Organic Chemistry, 1998, # 9, p. 2031 - 2038
  作者：Silva, Artur M. S.、Pinto, Diana C. G. A.、Tavares, Hilario R.、Cavaleiro, Jose A. S.、Jimeno, M. Luisa、Elguero, Jose

  DOI：——

  日期：——