4-hydroxy-3-(1-(4-methoxyphenyl)ethyl)-2H-chromen-2-one | 1198104-32-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-hydroxy-3-(1-(4-methoxyphenyl)ethyl)-2H-chromen-2-one
• 英文别名: 4-Hydroxy-3-[1-(4-methoxyphenyl)ethyl]chromen-2-one；4-hydroxy-3-[1-(4-methoxyphenyl)ethyl]chromen-2-one
• CAS: 1198104-32-3
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: AEWAGPMSFSZNHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯乙烯 、 4-羟基香豆素 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 4.0h， 以77%的产率得到4-hydroxy-3-(1-(4-methoxyphenyl)ethyl)-2H-chromen-2-one
  参考文献：
  名称：

  An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes

  摘要：

  DOI：

  10.1016/j.mencom.2021.01.039

文献信息

• Fe(ClO4)3·×H2O-Catalyzed direct C–C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles
  作者：Ponnaboina Thirupathi、Sung Soo Kim

  DOI：10.1016/j.tet.2010.02.063

  日期：2010.4

  mild and efficient Fe(ClO4)3·×H2O-catalyzed direct C–C bond coupling reactions of 1,3-dicarbonyl compounds, electron-rich arenes and heteroarenes and 4-hydroxycoumarin with secondary benzylic alcohols have been described. The benzylation of electron-rich arenes and heteroarenes leads to the synthesis of bis-symmetrical triarylmethanes. The present method is also applied to synthesis of an anti-coagulant

  已经描述了温和有效的Fe（ClO 4）3 ·×H 2 O催化的1,3-二羰基化合物，富电子芳烃和杂芳烃以及4-羟基香豆素与仲苄醇的直接C-C键偶联反应。富电子芳烃和杂芳烃的苄基化导致双对称三芳基甲烷的合成。本发明的方法也适用于合成一个的抗-coagulant化合物，4-羟基-3-（1,2,3,4-四氢萘-1-基）-2- ħ从市场上可买到的底物中得到-铬-2--2-酮（香豆基（B）），产率为85％。该协议的优点是范围广，条件温和，使用廉价的催化剂以及操作简便，因为水是唯一的副产品。
• Tungsten oxides: green and sustainable heterogeneous nanocatalysts for the synthesis of bioactive heterocyclic compounds
  作者：T. A. J. Siddiqui、Shoyebmohamad F. Shaikh、Balaji B. Totawar、Madhuri Dumpala、Mohd Ubaidullah、Badr M. Thamer、Rajaram S. Mane、Abdullah M. Al-Enizi

  DOI：10.1039/d0dt04238b

  日期：——

  Tungsten oxide (WO3) as an efficient heterogeneous catalyst was prepared via a simple hydrothermal route for the synthesis of a wide range of bioactive heterocyclic compounds. The present investigation deals with the rapid and low-cost synthesis of C-3-alkylated 4-hydroxycoumarin, chromene, and xanthene derivatives. WO3 nanorods (NRs) are successfully envisaged to catalyze desired transformations,

  氧化钨 (WO 3 ) 作为一种高效的多相催化剂是通过简单的水热途径制备的，用于合成范围广泛的生物活性杂环化合物。本研究涉及C -3-烷基化 4-羟基香豆素、色烯和呫吨衍生物的快速和低成本合成。WO 3纳米棒（NRs）被成功设想为催化所需的转化，展示了它们在催化中的广泛潜在应用。阐明了合成转化细节、最小催化量、优异的产品产率和形成这些杂环支架的合理反应机制。制备的WO 3NRs 的特征是分别通过 X 射线衍射、X 射线光电子能谱和场发射扫描电子显微镜测量来确认它们的结构、化学和形态参数。我们讨论了控制产物形成的因素，以及 WO 3 NRs的积极作用，这对于当前热条件研究中的底物活化至关重要。在此，报告了所制备化合物的详细合成和光谱信息。
• Direct Catalytic Benzylation of Hydroxycoumarin - Efficient Synthesis of Warfarin Derivatives and Analogues
  作者：Magnus Rueping、Boris Nachtsheim、Erli Sugiono

  DOI：10.1055/s-0029-1219936

  日期：2010.6

  Effective metal-catalyzed benzylations of 4-hydroxycoumarin have been developed. Employing a low amount of a cheap, nontoxic, and air-stable catalyst the 3-alkylated hydroxycoumarins were isolated in high yields after short reaction times. Applying this new methodology two widely used anticoagulants phenprocoumon and coumatetralyl were synthesized applying mild reaction conditions.

  已经开发出有效的金属催化4-羟基香豆素苄基化反应。使用少量廉价、无毒且稳定的催化剂，经过短时间反应后，获得了高产率的3-烷基化羟基香豆素。采用这种新方法，合成了两种广泛使用的抗凝剂苯普鲁孔和氟克洛络。
• Ganguly, Nemai C.; Chandra, Sumanta, Journal of the Indian Chemical Society, 2012, vol. 89, # 4, p. 547 - 555
  作者：Ganguly, Nemai C.、Chandra, Sumanta

  DOI：——

  日期：——
• Molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins with secondary benzyl alcohols
  作者：Xufeng Lin、Xixiang Dai、Zhenjun Mao、Yanguang Wang

  DOI：10.1016/j.tet.2009.09.007

  日期：2009.11

  A highly efficient method for the C-C bond formation via molecular iodine-catalyzed C3-alkylation reaction of 4-hydroxycoumarins with benzylic, benzhydrylic, allylic, and propargyl alcohols at 50 degrees C in MeNO2 is described. The 3-alkylated-4-hydroxycoumarins were obtained in good yields (up to 97%). By applying this reaction as the key step, a multi-substituted pyranocoumarin can easily be synthesized in a one-pot procedure. The advantages of this method are broad scope, mild conditions, and easy handling since water is the only side product. (C) 2009 Elsevier Ltd. All rights reserved.