7-demethoxyegonol-9(Z)-oleate | 1336884-97-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 7-demethoxyegonol-9(Z)-oleate
• 英文别名: 7-Demethoxyegonol Oleate；3-[2-(1,3-benzodioxol-5-yl)-1-benzofuran-5-yl]propyl (Z)-octadec-9-enoate
• CAS: 1336884-97-9
• 化学式: C₃₆H₄₈O₅
• 分子量: 560.774
• InChiKey: GIGIGVBVJACSBJ-KTKRTIGZSA-N

物化性质

• 沸点：
  661.5±55.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  41
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-demethoxyegonol-9(Z)-oleate 在 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 [2-Formyl-4-[3-(9-oxononanoyloxy)propyl]phenyl] 1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  Benzofurans from Styrax agrestis As Acetylcholinesterase Inhibitors: Structure–Activity Relationships and Molecular Modeling Studies

  摘要：

  An extract of Styrax agrestis fruits, collected in Vietnam, significantly inhibited acetylcholinesterase (AChE) in vitro. Bioassay-guided fractionation revealed three new egonol-type benzofurans: egonol-9(Z),12(Z) linoleate (1), 7-demethoxy-egonol-9(Z),12(Z) linoleate (2), and 7-demethoxyegonol oleate (4). Ten known egonol-type benzofurans were also isolated (3, 5, 6-13). In order to better understand structure activity relationships in this series, egonol derivatives 14-19 were prepared by chemical modifications and evaluated for their inhibition of AChE, butyrylcholinesterase (BChE), and AChE-induced A beta aggregation. Compounds 1-4 were the most potent inhibitors of the series, which exhibited inhibitory activity against AChE (IC50 1.4-3.1 mu M) and, for 1, A beta aggregation (77.6%). Molecular docking studies were also performed to investigate interaction of these compounds with the active site of AChE.

  DOI：

  10.1021/np200308j
• 作为产物：
  描述：

  水杨醛 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 碘 、 palladium diacetate 、 一氯化碘 、 caesium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 62.75h， 生成 7-demethoxyegonol-9(Z)-oleate
  参考文献：
  名称：

  通过简洁的合成策略快速获取基于苯并呋喃的天然产品

  摘要：

  描述了用于合成臭椿素 (1)、egonol (2)、homoegonol (3)、demethoxyegonol (4)、demethoxyhomoegonol (5) 和 Stemofuran A (6) 的简明策略。该方法涉及使用三芳基铋试剂生成苯并呋喃核的 Pd 催化的多米诺环化/偶联过程。随后的结构修改然后给出最终目标。最近分离的天然产物 egonol-9(Z)-12(Z)-linoleate (2a)、7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a) 和 7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a) 的高产合成-egonol-9(Z)-油酸酯 (4b) 也有报道。

  DOI：

  10.1002/ejoc.201600154

文献信息

• Rapid Access to Benzofuran-Based Natural Products through a Concise Synthetic Strategy
  作者：Maddali L. N. Rao、Venneti N. Murty

  DOI：10.1002/ejoc.201600154

  日期：2016.4

  A concise strategy is described for the synthesis of ailanthoidol (1), egonol (2), homoegonol (3), demethoxyegonol (4), demethoxyhomoegonol (5), and stemofuran A (6). This approach involves a Pd-catalysed domino cyclization/coupling process using triarylbismuth reagents for the generation of the benzofuran core. Subsequent structural modifications then give the final targets. The high yielding synthesis

  描述了用于合成臭椿素 (1)、egonol (2)、homoegonol (3)、demethoxyegonol (4)、demethoxyhomoegonol (5) 和 Stemofuran A (6) 的简明策略。该方法涉及使用三芳基铋试剂生成苯并呋喃核的 Pd 催化的多米诺环化/偶联过程。随后的结构修改然后给出最终目标。最近分离的天然产物 egonol-9(Z)-12(Z)-linoleate (2a)、7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a) 和 7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a) 的高产合成-egonol-9(Z)-油酸酯 (4b) 也有报道。
• Benzofurans from <i>Styrax agrestis</i> As Acetylcholinesterase Inhibitors: Structure–Activity Relationships and Molecular Modeling Studies
  作者：Jiawei Liu、Vincent Dumontet、Anne-Laure Simonin、Bogdan I. Iorga、Vincent Guerineau、Marc Litaudon、Van Hung Nguyen、Françoise Gueritte

  DOI：10.1021/np200308j

  日期：2011.10.28

  An extract of Styrax agrestis fruits, collected in Vietnam, significantly inhibited acetylcholinesterase (AChE) in vitro. Bioassay-guided fractionation revealed three new egonol-type benzofurans: egonol-9(Z),12(Z) linoleate (1), 7-demethoxy-egonol-9(Z),12(Z) linoleate (2), and 7-demethoxyegonol oleate (4). Ten known egonol-type benzofurans were also isolated (3, 5, 6-13). In order to better understand structure activity relationships in this series, egonol derivatives 14-19 were prepared by chemical modifications and evaluated for their inhibition of AChE, butyrylcholinesterase (BChE), and AChE-induced A beta aggregation. Compounds 1-4 were the most potent inhibitors of the series, which exhibited inhibitory activity against AChE (IC50 1.4-3.1 mu M) and, for 1, A beta aggregation (77.6%). Molecular docking studies were also performed to investigate interaction of these compounds with the active site of AChE.