2-cinnamyl-3,5-dimethoxyphenol | 332386-33-1

• 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: 2-cinnamyl-3,5-dimethoxyphenol
• 英文别名: 2-[(E)-cinnamyl]-3,5-dimethoxy-phenol；3,5-dimethoxy-2-[(E)-3-phenylprop-2-enyl]phenol
• CAS: 332386-33-1
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: HYTWSOGHGJKHFH-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cinnamyl-3,5-dimethoxyphenol 在 甲醇 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 L-Selectride 、 potassium carbonate 、 戴斯-马丁氧化剂 、 N-甲基吗啉氧化物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成 5,7-dimethoxy-2-phenylchroman-3-yl 4-acetoxy-3-(3-methylbut-2-en-1-yl)benzoate
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor

  摘要：

  Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90; however, structure activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Antiproliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of the four most potent analogues was further evaluated by Western blot analyses and degradation of Hsp90-dependent client proteins. The prenyl-substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as a novel scaffold that exhibits Hsp90 inhibitory activity.

  DOI：

  10.1021/jo401027r
• 作为产物：
  描述：

  (E)-1-(2-羟基-4,6-二甲氧基苯基)-3-苯基丙酮 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.17h， 生成 2-cinnamyl-3,5-dimethoxyphenol
  参考文献：
  名称：

  Deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction

  摘要：

  An efficient protocol for deoxygenation of alpha,beta-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction is described. The reaction shows very good selectivity and tolerates a wide range of functionalities on alpha,beta-unsaturated acylphenols, giving corresponding 2-allylphenols in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.109

文献信息

• Enantioselective Synthesis of Epigallocatechin-3-gallate (EGCG), the Active Polyphenol Component from Green Tea
  作者：Lianhai Li、Tak Hang Chan

  DOI：10.1021/ol000394z

  日期：2001.3.1

  [GRAPHICS]Enantioselective synthesis of epigallocatechin-3-gallate (EGCG, 3b), the active polyphenol component from green tea, has been achieved by using a stereospecific cyclization of the Sharpless asymmetric dihydroxylation product 7c as the key step.
• Synthesis and Structure–Activity Relationships of EGCG Analogues, a Recently Identified Hsp90 Inhibitor
  作者：Anuj Khandelwal、Jessica A. Hall、Brian S. J. Blagg

  DOI：10.1021/jo401027r

  日期：2013.8.16

  Epigallocatechin-3-gallate (EGCG), the principal polyphenol isolated from green tea, was recently shown to inhibit Hsp90; however, structure activity relationships for this natural product have not yet been produced. Herein, we report the synthesis and biological evaluation of EGCG analogues to establish structure activity relationships between EGCG and Hsp90. All four rings as well as the linker connecting the C- and the D-rings were systematically investigated, which led to the discovery of compounds that inhibit Hs90 and display improvement in efficacy over EGCG. Antiproliferative activity of all the analogues was determined against MCF-7 and SKBr3 cell lines and Hsp90 inhibitory activity of the four most potent analogues was further evaluated by Western blot analyses and degradation of Hsp90-dependent client proteins. The prenyl-substituted aryl ester of 3,5-dihydroxychroman-3-ol ring system was identified as a novel scaffold that exhibits Hsp90 inhibitory activity.
• Deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction
  作者：Hu Yuan、Hao Chen、Huizi Jin、Bo Li、Rongcai Yue、Ji Ye、Yunheng Shen、Lei Shan、Qingyan Sun、Weidong Zhang

  DOI：10.1016/j.tetlet.2013.02.109

  日期：2013.5

  An efficient protocol for deoxygenation of alpha,beta-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction is described. The reaction shows very good selectivity and tolerates a wide range of functionalities on alpha,beta-unsaturated acylphenols, giving corresponding 2-allylphenols in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.