(E)-2'-hydroxy-3,4-dimethoxy-4'-(phenylmethoxy)chalcone | 95560-62-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2'-hydroxy-3,4-dimethoxy-4'-(phenylmethoxy)chalcone
• 英文别名: 4'-Benzyloxy-2'-oxy-3,4-dimethoxy-chalkon；(E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 95560-62-6
• 化学式: C₂₄H₂₂O₅
• 分子量: 390.436
• InChiKey: YBENTYHMIGFMEI-XYOKQWHBSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  602.8±55.0 °C(predicted)
• 密度：
  1.216±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2'-hydroxy-3,4-dimethoxy-4'-(phenylmethoxy)chalcone 、 氯甲酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors

  摘要：

  We herein describe the synthesis and positive modulatory activities of a small library of flavan-3-ol derivatives on alpha(1)beta(2)gamma(2L) GABA(A) receptors. Structure-activity relationships of various substituents on the A, B and C rings were evaluated in a functional electrophysiological assay. A trans configuration and a 3-acetoxy moiety are essential for activity. Substitution of the B ring appears to be well tolerated, with substituents on the A ring playing a major role in determining activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.062
• 作为产物：
  描述：

  4-苄氧基-2-羟基苯乙酮 、 3,4-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以68%的产率得到(E)-2'-hydroxy-3,4-dimethoxy-4'-(phenylmethoxy)chalcone
  参考文献：
  名称：

  Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors

  摘要：

  We herein describe the synthesis and positive modulatory activities of a small library of flavan-3-ol derivatives on alpha(1)beta(2)gamma(2L) GABA(A) receptors. Structure-activity relationships of various substituents on the A, B and C rings were evaluated in a functional electrophysiological assay. A trans configuration and a 3-acetoxy moiety are essential for activity. Substitution of the B ring appears to be well tolerated, with substituents on the A ring playing a major role in determining activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.062

文献信息

• Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors
  作者：Kenneth N. Mewett、Sebastian P. Fernandez、Anmol K. Pasricha、Alice Pong、Steven O. Devenish、David E. Hibbs、Mary Chebib、Graham A.R. Johnston、Jane R. Hanrahan

  DOI：10.1016/j.bmc.2009.08.062

  日期：2009.10

  We herein describe the synthesis and positive modulatory activities of a small library of flavan-3-ol derivatives on alpha(1)beta(2)gamma(2L) GABA(A) receptors. Structure-activity relationships of various substituents on the A, B and C rings were evaluated in a functional electrophysiological assay. A trans configuration and a 3-acetoxy moiety are essential for activity. Substitution of the B ring appears to be well tolerated, with substituents on the A ring playing a major role in determining activity. (C) 2009 Elsevier Ltd. All rights reserved.