3-(3,4,5-trimethoxyphenyl)propenol acetate | 87200-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3,4,5-trimethoxyphenyl)propenol acetate
• 英文别名: (E)-3-(3,4,5-trimethoxyphenyl)allyl acetate；3-acetoxy-1t-(3,4,5-trimethoxy-phenyl)-propene；3-Acetoxy-1t-(3,4,5-trimethoxy-phenyl)-propen；[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enyl] acetate
• CAS: 87200-84-8
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: IMLQOKDTSYBFHF-AATRIKPKSA-N

物化性质

• 沸点：
  397.9±42.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-二甲基-2,6-二氢-吡喃并[3,2-c]喹啉-5-酮 、 3-(3,4,5-trimethoxyphenyl)propenol acetate 以 neat (no solvent) 为溶剂， 反应 16.0h， 以9%的产率得到(1RS,2RS,2aRS,10aSR)-1-acetoxymethyl-10,10-dimethyl-2-(3,4,5-trimethoxyphenyl)-1,2,2a,4,10,10a-hexahydro-3H-cyclobuta[4,5]pyrano[3,2-c]quinolin-3-one
  参考文献：
  名称：

  Euodenine A: A Small-Molecule Agonist of Human TLR4

  摘要：

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

  DOI：

  10.1021/jm401321v
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 苄基三乙基氯化铵 作用下， 以 吡啶 、 乙醚 、 氯仿 、 水 为溶剂， 反应 9.0h， 生成 3-(3,4,5-trimethoxyphenyl)propenol acetate
  参考文献：
  名称：

  Ehret, Charles; Maupetit, Pierre, Phytochemistry, 1982, vol. 21, # 12, p. 2984 - 2985

  摘要：

  DOI：

文献信息

• Euodenine A: A Small-Molecule Agonist of Human TLR4
  作者：Juliette E. Neve、Hasanthi P. Wijesekera、Sandra Duffy、Ian D. Jenkins、Justin A. Ripper、Simon J. Teague、Marc Campitelli、Agatha Garavelas、George Nikolakopoulos、Phuc V. Le、Priscila de A. Leone、Ngoc B. Pham、Philip Shelton、Neil Fraser、Anthony R. Carroll、Vicky M. Avery、Christopher McCrae、Nicola Williams、Ronald J. Quinn

  DOI：10.1021/jm401321v

  日期：2014.2.27

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.
• Ehret, Charles; Maupetit, Pierre, Phytochemistry, 1982, vol. 21, # 12, p. 2984 - 2985
  作者：Ehret, Charles、Maupetit, Pierre

  DOI：——

  日期：——