3,4-bis(4-methoxyphenyl)furan | 52381-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3,4-bis(4-methoxyphenyl)furan
• CAS: 52381-02-9
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: HBDJFBHKIYTRCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-bis(4-methoxyphenyl)furan 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到3,4-bis(4-hydroxyphenyl)furan
  参考文献：
  名称：

  Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

  摘要：

  To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross coupling of aryl boronic acids with bromo-thiophenes and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols, all contribute to binding affinity and subtype selective. Most of the bis(hydroxyphenyl)-thiophenes were ER beta selective, whereas the tris(hydroxyphenyl)-thiophenese were ER alpha selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity, in reporter gene assays, giving maximal activities 2-3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11 Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.

  DOI：

  10.1021/jm400157e
• 作为产物：
  描述：

  3,4-二溴呋喃 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 以48%的产率得到3,4-bis(4-methoxyphenyl)furan
  参考文献：
  名称：

  Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

  摘要：

  To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross coupling of aryl boronic acids with bromo-thiophenes and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols, all contribute to binding affinity and subtype selective. Most of the bis(hydroxyphenyl)-thiophenes were ER beta selective, whereas the tris(hydroxyphenyl)-thiophenese were ER alpha selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity, in reporter gene assays, giving maximal activities 2-3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11 Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.

  DOI：

  10.1021/jm400157e

文献信息

• Novel Synthesis of 1,4-Dialkoxy-5,6,7,8-multisubstituted-2,3-dicyanonaphthalenes through Electron Transfer from Mg Metal and Efficient Development of New Naphthalocyanines
  作者：Hirofumi Maekawa、Ikuzo Nishiguchi、Takeshi Miyazaki、Aiko Harada、Yoshimasa Yamamoto

  DOI：10.1055/s-0030-1259910

  日期：2011.4

  Novel methods for efficient synthesis of 1,4-diamyloxy-5,6,7,8-multisubstituted-2,3-dicyanonaphthalenes were successfully developed, starting from easily available 2,3-dicyanohydroquinone as a common single compound through only three steps, the first dibromination of 2,3-dicyanohydroquinone, the second Mitsunobu dialkylation of 2,3-dicyano-5,6-diboromo-1,4-hydroquinone, and the last Diels-Alder-type of cycloaddition between 1,4-alkoxy-2,3-dicyano-5,6-diboromobenzenes and multisubstituted furans, followed by reductive deoxygenation with Mg turning. The obtained 1,4-diamyloxy-5,6,7,8-multisubstituted-2,3-dicyanonaphthalenes were easily transformed into the corresponding naphthalocyanines in 20-45% yields which showed their λmax at 867-892 nm.

  成功开发了合成1,4-二氨基氧-5,6,7,8-多取代-2,3-二氰基萘的高效新方法。该方法从易得的2,3-二氰基氢醌出发，仅通过三步反应：首先是2,3-二氰基氢醌的二溴化反应，其次是2,3-二氰基-5,6-二溴-1,4-氢醌的 Mitsunobu 二烷基化反应，最后是1,4-烷氧基-2,3-二氰基-5,6-二溴苯与多取代呋喃的 Diels-Alder 型环加成反应，随后通过镁还原脱氧反应得到产物。所得的1,4-二氨基氧-5,6,7,8-多取代-2,3-二氰基萘可以轻松转化为相应的萘酞菁衍生物，产率为20-45%，其最大吸收波长在867-892 nm之间。
• YOSHINA SHIGETAKA; YAMAMOTO KATSUMI, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR. <YKKZ-AJ>, 1975, 95+
  作者：YOSHINA SHIGETAKA、 YAMAMOTO KATSUMI

  DOI：——

  日期：——