3-(2-(benzo[d][1,3]dioxol-5-yl)-7-methoxybenzo[b]furan-5-yl)propyl acetate | 15434-00-1

• 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: 3-(2-(benzo[d][1,3]dioxol-5-yl)-7-methoxybenzo[b]furan-5-yl)propyl acetate
• 英文别名: 5-(3''-acetoxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl)benzofuran；3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propyl acetate；5-(3-acetyloxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran；5-(3-acetoxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran；egonol acetate；egonolacetate
• CAS: 15434-00-1
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: KOUYRIXNPBTZIN-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  525.3±50.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-(benzo[d][1,3]dioxol-5-yl)-7-methoxybenzo[b]furan-5-yl)propyl acetate 在 sodium hydroxide 、 臭氧 、 乙酸乙酯 作用下， 生成 2-hydroxy-5-(3-hydroxy-propyl)-3-methoxy-benzaldehyde
  参考文献：
  名称：

  Kawai; Yoshimura, Chemische Berichte, 1938, vol. 71, p. 2415,2419

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(3-acetoxyprop-1-ynyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以89%的产率得到3-(2-(benzo[d][1,3]dioxol-5-yl)-7-methoxybenzo[b]furan-5-yl)propyl acetate
  参考文献：
  名称：

  苯并噻吩酚，烯醇及相关类似物的全合成

  摘要：

  已开发出有效且通用的合成方案，用于全合成艾兰地洛尔，烯醇和一些相关类似物。这里描述的关键转化涉及苯并呋喃和Sonogashira偶联的两步构建，并且从容易获得的试剂开始证明是方便有效的。 苯并呋喃-交叉偶联-McMurry反应-Sonogashira偶联-天然产物

  DOI：

  10.1055/s-0029-1219224

文献信息

• 2-Phenylbenzo[ b ]furans: Synthesis and promoting activity on estrogen biosynthesis
  作者：Wenchen Pu、Yun Yuan、Danfeng Lu、Xin Wang、Hanwei Liu、Chun Wang、Fei Wang、Guolin Zhang

  DOI：10.1016/j.bmcl.2016.10.013

  日期：2016.11

  2-phenylbenzo[b]furan glycosides could promote estrogen biosynthesis. To find high active 2-phenylbenzo[b]furans, fifty-four 2-phenylbenzo[b]furans were prepared via four strategies according to corresponding substrate scopes. Biological evaluation in HEK293A cells showed that some compounds exhibited promotive activity on estrogen biosynthesis. 2-(4-Chlorophenyl)-7-methoxybenzo[b]furan possessed the

  雌激素的生物合成对人类的许多生理过程至关重要。雌激素水平异常与多种疾病密切相关，包括乳腺癌和骨质疏松症。以前我们发现2-苯基苯并[b]呋喃糖苷可以促进雌激素的生物合成。为了找到高活性的2-苯基苯并[b]呋喃，根据相应的底物范围，通过四种策略制备了五十四种2-苯基苯并[b]呋喃。HEK293A细胞的生物学评估表明，某些化合物对雌激素的生物合成具有促进作用。2-（4-氯苯基）-7-甲氧基苯并[b]呋喃具有最高的活性，EC50值为14.68μM。此外，这些化合物不会影响HEK292A细胞中的芳香化酶表达，
• New benzofurans related to egonol from immature seeds of Styrax obassia
  作者：Masahide Takanashi、Yasuomi Takizawa

  DOI：10.1016/0031-9422(88)80314-5

  日期：——

  Abstract Three new benzofurans have been isolated from immature seeds of Styrax obassia . Their structures have been established as 5-[3-(2-methylbutanoyloxy)propyl]-7-methoxy-2-(3′,4′-methylene dioxyphenyl)benzofuran ( 3 ), 5-[3-(2-methybutanoyloxy)propyl]-2-(3′,4′-methylenedioxy-phenyl)benzofuran ( 5 ), and 5-[3-(β- d -glucopyranosyloxy)propyl]-7-methoxy-2-(3′,4′-methylenedioxyphenyl)benzofuran ( 6 ), respectively

  摘要 从Styrax obassia 的未成熟种子中分离到了3 个新的苯并呋喃。它们的结构已确定为 5-[3-(2-methylbutanoyloxy)propyl]-7-methoxy-2-(3',4'-methylene dioxyphenyl)benzofuran (3), 5-[3-(2-methybutanoyloxy)丙基]-2-(3',4'-亚甲二氧基-苯基)苯并呋喃 (5), 和 5-[3-(β-d-吡喃葡萄糖基氧基)丙基]-7-甲氧基-2-(3',4'-亚甲基二氧苯基)苯并呋喃 (6)，分别基于它们的化学和光谱特性以及酶促反应。还鉴定了 Egonol 醋酸酯 (2)。
• Kawai; Sugiyama, Chemische Berichte, 1938, vol. 71, p. 2421,2427
  作者：Kawai、Sugiyama

  DOI：——

  日期：——
• Cyclooxygenase inhibitory properties of<i>nor</i>-neolignans from<i>Styrax pohlii</i>
  作者：Camila S. Bertanha、Caio G. Braguine、Ana C.G. Moraes、Valéria M.M. Gimenez、Milton Groppo、Márcio L.A. Silva、Wilson R. Cunha、Ana H. Januário、Patrícia M. Pauletti

  DOI：10.1080/14786419.2012.671320

  日期：2012.12

  Chemical investigation of the n-hexane and EtOAc fractions of the ethanolic extract from Styrax pohlii (Styracaceae) aerial parts resulted in the isolation of the benzofuran nor-neolignan derivatives egonol (1), homoegonol (2), homoegonol gentiobioside (3), homoegonol glucoside (4) and egonol gentiobioside (5). This is the first report of compounds 1-5 in S. pohlii. Compounds 1-5, the acetyl derivatives 1a and 2a, the ethanolic extract (EE), the n-hexane fraction (HF) and EtOAc fraction (EF) were tested for their inhibitory activities against COX-1 and COX-2. The results showed that EE, HF, EF and compounds 1-5 and 1 a-2 a shown weak to moderate inhibition of COX-1 and COX-2. Among the assayed nor-neolignans, 4 gave a COX-1 inhibition of 35.7% at 30 mu M. Compound 5 displayed a COX-2 inhibition of 19.7% at 30 mu M.
• Synthesis of egonol derivatives and their antimicrobial activities
  作者：Safiye Emirdağ-Öztürk、Tamer Karayildirim、Hüseyin Anil

  DOI：10.1016/j.bmc.2010.12.044

  日期：2011.2

  Eighteen derivatives of egonol (A-R) were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC 6633, Candida albicans ATCC 10231 and Escherichia coli ATCC 8739 microorganisms comparing with egonol. The obtained data reported that compound B exhibited improved activities against all tested bacteria than egonol, others have shown different range of activities. (C) 2010 Elsevier Ltd. All rights reserved.