5-methoxy-4-phenyl-2H-chromen-2-one | 36914-76-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 5-methoxy-4-phenyl-2H-chromen-2-one
• 英文别名: 5-Methoxy-4-phenyl-2H-1-benzopyran-2-one；5-methoxy-4-phenylchromen-2-one
• CAS: 36914-76-8
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: GHZPHMZVYPAZSF-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  437.6±45.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  5-methoxy-4-phenyl-2H-chromen-2-one 在 sodium hydroxide 、 dipotassium peroxodisulfate 作用下， 生成 6-hydroxy-5-methoxy-4-phenyl-coumarin
  参考文献：
  名称：

  Ahluwalia et al., Proceedings - Indian Academy of Sciences, Section A, 1957, # 45, p. 293,295

  摘要：

  DOI：
• 作为产物：
  描述：

  4-hydroxy-5-methoxy coumarin 在 四(三苯基膦)钯 四氯化碳 、 sodium carbonate 、 三苯基膦 作用下， 以 乙醇 、 苯 为溶剂， 反应 26.0h， 生成 5-methoxy-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins

  摘要：

  在铃木反应条件下，钯催化 4-氯或 4-溴香豆素 1-4 与芳基硼酸 5-13 的偶联反应是获得 4-芳基香豆素的有效途径。在改良的铃木反应条件下，使用碘化铜（I）作为辅助催化剂，将 4-三氟甲基-磺酰氧基香豆素 35-38 与芳基硼酸进行处理，也能以良好的收率（70-97%）获得这些 4-芳基香豆素。

  DOI：

  10.1039/p19960002591

文献信息

• Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes
  作者：Olesia Zaitceva、Valérie Bénéteau、Dmitry S. Ryabukhin、Ivan I. Eliseev、Mikhal A. Kinzhalov、Benoit Louis、Aleksander V. Vasilyev、Patrick Pale

  DOI：10.1016/j.tet.2020.131029

  日期：2020.4

  Cyclometalated (ppy)PtII complexes (ppy = 2-phenylpyridinato-C2,N) catalyze the intramolecular cyclization of aryl propynoates to form coumarins and benzocoumarins. The complex [(ppy)PtCl(MeCN)] (5 mol %) was the most active and efficient catalyst for such reaction, especially in the presence of AgSbF6 (15 mol %) in 1,2-dichloroethane. With this catalytic system, a wide range of substituents and functional

  环金属化（ppy）Pt II配合物（ppy = 2-苯基吡啶基-C 2，N）催化丙酸芳基酯的分子内环化反应，形成香豆素和苯并香豆素。配合物[（ppy）PtCl（MeCN）]（5 mol％）是用于该反应的最活性和最有效的催化剂，尤其是在存在1,2-二氯乙烷的AgSbF 6（15 mol％）的情况下。通过这种催化体系，证明了广泛的取代基和官能团与环化过程兼容，从而导致了多种取代的香豆素和苯并香豆素（22个实例，占77–99％）
• Selectivity Controlled Palladium-Catalyzed Carbonylative Synthesis of Propiolates and Chromenones from Phenols and Alkynes
  作者：Fengxiang Zhu、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.8b01368

  日期：2018.6.1

  interesting selectivity-controlled palladium-catalyzed oxidative carbonylation procedure for the synthesis of propiolates and chromenones has been developed. Starting from phenols and alkynes, under slightly different conditions, various propiolates and chromenones can be isolated in moderate to good yields. Additionally, this also presents the first example of direct carbonylative annulation of nonpreactivated

  已经开发了一种有趣的选择性控制的钯催化的氧化羰基化方法，用于合成丙酸酯和色农酮。从苯酚和炔烃开始，在略有不同的条件下，可以以中等到良好的产率分离出各种丙酸酯和色农酮。另外，这也提供了非预活化酚和末端炔烃直接羰基环化以生产色农酮的第一个例子。
• Synthesis of highly functionalized flavones and chromones using cycloacylation reactions and C-3 functionalization. A total synthesis of hormothamnione
  作者：Lynda W. McGarry、Michael R. Detty

  DOI：10.1021/jo00301a027

  日期：1990.7
• Seshadri; Varadarajan, Proceedings - Indian Academy of Sciences, Section A, 1952, # 5, p. 75,80
  作者：Seshadri、Varadarajan

  DOI：——

  日期：——
• Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization
  作者：Stefan J Pastine、So Won Youn、Dalibor Sames

  DOI：10.1016/j.tet.2003.05.003

  日期：2003.11

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.