3-allyl-7-methoxy-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-allyl-7-methoxy-4H-chromen-4-one
• 英文别名: 7-Methoxy-3-prop-2-enylchromen-4-one
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: FLBWGYZAWHHOJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  间二甲苯 、 3-allyl-7-methoxy-4H-chromen-4-one 在 palladium diacetate 、 三氟乙酸 作用下， 反应 20.0h， 以83%的产率得到3-(1-(2,4-dimethylphenyl)propyl)-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Pd催化的3-烯丙基色酮的顺序氢化反应和烯化反应。

  摘要：

  在本文中，提出了一种新颖的方法，用于富电子芳烃的3-烯丙基色酮的区域选择性α-或γ-氢芳基化。该研究结果表明区域选择性取决于烯丙基的γ-位上的取代基。氢或烷基取代有利于α-氢芳基化，而芳基取代有利于γ-氢芳基化。该方法学提供了实现3-烯丙基色酮的α-或γ-选择性加氢芳基化的有效手段。也已经报道了将α-氢芳基化用于执行Pd催化的一锅顺序α-氢芳基化和π-螯合辅助的烯烃化反应。

  DOI：

  10.1039/c9ob01147a
• 作为产物：
  描述：

  丹皮酚 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 potassium tert-butylate 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.75h， 生成 3-allyl-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 4H-benzopyran-4-one derivatives as nonsteroidal antiestrogens

  摘要：

  The preparation and characterization of some novel 2- and 3-substituted-7-methoxy-4H-1-benzopyran-4-one are presented. The synthesized compounds were evaluated for their uterotrophic, antiuterotrophic and antiimplantation activities in mature female albino rats. 3-Benzyl-7-methoxy-4H-1-benzopyran-4-one (14) showed the highest uterotrophic activity (87%) based on dry uterine weight gain. The antifertility activity, as assessed by the post-coital antiimplantation activity test, was of weak potency for most compounds (14-29%). Among the products, the 2-(4'-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one (19) exhibited the highest antiestrogenic activity of 65%. It also elicited 31% of the uterotrophic activity of estradiol. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01218-1

文献信息

• Pd-Catalyzed sequential hydroarylation and olefination reactions of 3-allylchromones
  作者：Yi-En Liang、Chia-Ling Lu、Wen-Tai Li

  DOI：10.1039/c9ob01147a

  日期：——

  efficient means to achieve the α- or γ-selective hydroarylation of 3-allylchromones. Application of α-hydroarylation to perform Pd-catalyzed one-pot sequential α-hydroarylation and π-chelation-assisted olefination has also been reported.

  在本文中，提出了一种新颖的方法，用于富电子芳烃的3-烯丙基色酮的区域选择性α-或γ-氢芳基化。该研究结果表明区域选择性取决于烯丙基的γ-位上的取代基。氢或烷基取代有利于α-氢芳基化，而芳基取代有利于γ-氢芳基化。该方法学提供了实现3-烯丙基色酮的α-或γ-选择性加氢芳基化的有效手段。也已经报道了将α-氢芳基化用于执行Pd催化的一锅顺序α-氢芳基化和π-螯合辅助的烯烃化反应。
• Synthesis and biological evaluation of some novel 4H-benzopyran-4-one derivatives as nonsteroidal antiestrogens
  作者：Khadiga Ahmed Ismail、Tarek Abd El Aziem

  DOI：10.1016/s0223-5234(01)01218-1

  日期：2001.3

  The preparation and characterization of some novel 2- and 3-substituted-7-methoxy-4H-1-benzopyran-4-one are presented. The synthesized compounds were evaluated for their uterotrophic, antiuterotrophic and antiimplantation activities in mature female albino rats. 3-Benzyl-7-methoxy-4H-1-benzopyran-4-one (14) showed the highest uterotrophic activity (87%) based on dry uterine weight gain. The antifertility activity, as assessed by the post-coital antiimplantation activity test, was of weak potency for most compounds (14-29%). Among the products, the 2-(4'-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one (19) exhibited the highest antiestrogenic activity of 65%. It also elicited 31% of the uterotrophic activity of estradiol. (C) 2001 Editions scientifiques et medicales Elsevier SAS.