2-(3,4-dimethoxyphenyl)-3-iodo-4H-4-chromenone | 645387-26-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3,4-dimethoxyphenyl)-3-iodo-4H-4-chromenone
• 英文别名: 3-iodo-3',4'-dimethoxyflavone；3-Iod-3',4'-dimethoxy-flavan-4-on；4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3-iodo-；2-(3,4-dimethoxyphenyl)-3-iodochromen-4-one
• CAS: 645387-26-4
• 化学式: C₁₇H₁₃IO₄
• 分子量: 408.192
• InChiKey: UWUDUFFLGXHCOC-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C
• 沸点：
  460.554±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.697±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-3-iodo-4H-4-chromenone 在 铜 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以64%的产率得到3',3''',4',4'''-tetramethoxy-3,3''-biflavone
  参考文献：
  名称：

  Synthesis and antifungal activities of natural and synthetic biflavonoids

  摘要：

  The synthesis of some natural and synthetic biflavonoids was performed in good overall yields starting from readily available materials via high yielding aldol and Ullmann condensations. Some of these compounds, especially bichalcones, display an interesting activity against fungi, higher than that of the corresponding monomers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.010
• 作为产物：
  描述：

  (2E)-3-(3,4-二甲氧基苯基)-1-(2-羟基苯基)-2-丙烯-1-酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以72%的产率得到2-(3,4-dimethoxyphenyl)-3-iodo-4H-4-chromenone
  参考文献：
  名称：

  Synthesis and antifungal activities of natural and synthetic biflavonoids

  摘要：

  The synthesis of some natural and synthetic biflavonoids was performed in good overall yields starting from readily available materials via high yielding aldol and Ullmann condensations. Some of these compounds, especially bichalcones, display an interesting activity against fungi, higher than that of the corresponding monomers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.010

文献信息

• Palladium catalyzed reaction in aqueous DMF: synthesis of 3-alkynyl substituted flavones in the presence of prolinol
  作者：Manojit Pal、Venkataraman Subramanian、Karuppasamy Parasuraman、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.tet.2003.10.003

  日期：2003.11

  (S)-Prolinol facilitated the coupling reaction of terminal alkynes with 3-iodoflavone under palladium–copper catalysis in aqueous DMF affording a mild and convenient method for the synthesis of 3-alkynyl substituted flavones of potential biological interest.

  （S）-脯氨醇促进了在DMF水溶液中钯-铜催化下末端炔烃与3-碘黄酮的偶联反应，为合成具有潜在生物学意义的3-炔基取代的黄酮提供了一种温和而便捷的方法。
• A Route to Highly Functionalized Stereospecific trans-Aminated Aurones from 3-Bromoflavones with Aniline and N-Phenylurea via a Domino Aza-Michael Ring Opening and Cyclization Reactions
  作者：Naseem Ahmed、Iram Parveen

  DOI：10.1055/s-0037-1610662

  日期：2019.2

  the requirement of additives and ligands, and offers broad substrate scope. A facile cascade reaction is reported via aza-Michael addition, ring opening, and cyclization between 3-bromoflavone and aniline derivatives or N-phenylurea in the presence of KOt-Bu and CuI in DMF under mild reaction conditions. Products were obtained as stereospecific trans-aminated aurones in good to excellent yields (61–83%)

  摘要 据报道，在温和的反应条件下，在KO t -Bu和CuI存在的情况下，通过aza-Michael加成，开环和3-溴黄酮与苯胺衍生物或N-苯基脲之间的环化反应，可实现简单的级联反应。产品以良好的立体效果（61-83％）获得为立体有择的反胺化的金黄色。我们的协议操作简便，操作成功，避免了添加剂和配体的需求，并提供了广泛的底物范围。 据报道，在温和的反应条件下，在KO t -Bu和CuI存在的情况下，通过aza-Michael加成，开环和3-溴黄酮与苯胺衍生物或N-苯基脲之间的环化反应，可实现简单的级联反应。产品以良好的立体效果（61-83％）获得为立体有择的反胺化的金黄色。我们的协议操作简便，操作成功，避免了添加剂和配体的需求，并提供了广泛的底物范围。
• Regioselective Hydrodehalogenation of Aromatic α‐ and β‐Halo carbonyl Compounds by CuI in Isopropanol
  作者：Iram Parveen、Danish Khan、Naseem Ahmed

  DOI：10.1002/ejoc.201801385

  日期：2019.1.31

  An efficient and regioselective hydrodehalogenation of aromatic α‐ and β‐halo carbonyl compounds has been developed using CuI in isopropanol under basic condition. This reaction system effectively reduces chloride, bromide and iodide groups and affords high yield (up to 97 %) as carbonyl compounds. The method is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically

  在碱性条件下，使用CuI在异丙醇中开发了一种有效的且对区域选择性的芳香族α-和β-卤代羰基化合物进行加氢脱卤的方法。该反应体系可有效还原氯，溴和碘基团，并以羰基化合物形式提供高收率（最高97％）。该方法是环境友好的，并且显示出对多种电子富和取代基的优异耐受性。
• Regio- and Stereospecific Synthesis of Novel 3-Enynyl-Substituted Thioflavones/Flavones Using a Copper-Free Palladium-Catalyzed Reaction
  作者：Manojit Pal、Rambabu Dakarapu、Karuppasamy Parasuraman、Venkataraman Subramanian、Koteswar Rao Yeleswarapu

  DOI：10.1021/jo050828+

  日期：2005.9.1

  3-enynyl substituted flavones/thioflavones were synthesized via a sequential one-pot procedure using copper-free palladium-catalyzed cross coupling in a simple synthetic operation. The cross coupling between 3-iodo(thio)flavone and a broad range of terminal alkynes was carried out in the presence of Pd(PPh3)2Cl2 and triethylamine to afford the corresponding 3-enynyl derivatives in a regio- and stereoselective

  通过简单的合成操作，使用无铜钯催化的交叉偶联，通过连续的一锅法合成了各种3-烯丙基取代的黄酮/硫代黄酮。在Pd（PPh 3）2 Cl 2存在下进行3-碘（硫代）黄酮与各种末端炔烃的交叉偶联和三乙胺以区域和立体选择性的方式得到相应的3-烯基衍生物。通过使用3当量的末端炔烃可获得最佳结果。不管该（硫代）黄酮环上以及在除芳基炔烃之外的末端炔烃中存在的取代基如何，该方法都能很好地进行。该反应是非常区域选择性的，将末端炔的取代基置于与（硫代）黄酮环相连的双键的远端。发现在分离出的产物中，（硫）黄酮基和炔基部分跨双键的取向是同位的。在钯催化剂的存在下串联式CC键形成反应合理化了偶联产物的形成。催化过程显然涉及杂芳基钯的形成，在末端炔烃的C-C三键上进行区域选择性加成，随后再用另一摩尔炔烃置换钯。本方法学可用于在黄酮和硫代黄酮环的C-3位上引入烯基部分，以提供具有潜在生物学意义的新型化合物。在CuI的存
• Palladium mediated stereospecific synthesis of 3-enynyl substituted thioflavones/flavones
  作者：Manojit Pal、Karuppasamy Parasuraman、Venkataraman Subramanian、Rambabu Dakarapu、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.tetlet.2004.01.113

  日期：2004.3

  The stereocontrolled synthesis of enynes has been accomplished via a sequential Heck-Sonogashira reaction in a simple synthetic operation. A variety of terminal alkynes were reacted with 3-iodo(thio)flavone in the presence of a palladium catalyst and a copper salt affording a mild and one-pot method for the first synthesis of the corresponding 3-enynyl and/or alkynyl derivatives. The mechanism and scope of the reaction are discussed. (C) 2004 Elsevier Ltd. All rights reserved.