5,7-dimethoxy-4-(4-methoxyphenyl)-2H-1-benzopyran-2-one | 74512-60-0

• 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: 5,7-dimethoxy-4-(4-methoxyphenyl)-2H-1-benzopyran-2-one
• 英文别名: 5,7-dimethoxy-4-(4-methoxyphenyl)-2H-chromen-2-one；5,7,4'-Trimethoxy-4-phenyl-2H-1-benzopyran-2-one；5,7-dimethoxy-4-(4-methoxyphenyl)chroman-2-one；5,7-dimethoxy-4-(4-methoxyphenyl)coumarin；4',5,7-trimethoxy-4-phenylcoumarin；5,7,4'-trimethoxy-4-phenylcoumarin；5,7-dimethoxy-4-(4-methoxyphenyl)chromen-2-one
• CAS: 74512-60-0
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: LUAQJOITTQBGCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,5R)-3,5-dimethylpiperidine 、 5,7-dimethoxy-4-(4-methoxyphenyl)-2H-1-benzopyran-2-one 以 N,N-二甲基乙酰胺 为溶剂， 反应 8.0h， 生成 1-(cis-3,5-dimethylpiperidin-1-yl)-3-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  Identification of Potent and Selective Diphenylpropanamide RORγ Inhibitors

  摘要：

  Retinoic acid-related orphan receptor ROR gamma t plays a pivotal role in the differentiation of T(H)17 cells. Antagonizing ROR gamma t transcriptional activity is a potential means to treat T(H)17-related autoimmune diseases. Herein, we describe the identification of a series of diphenylpropanamides as novel and selective ROR gamma antagonists. Diphenylpropanamide 4n inhibited the transcriptional activity of ROR gamma t, but not ROR alpha, in cells. In addition, it suppressed human T(H)17 cell differentiation at submicromolar concentrations.

  DOI：

  10.1021/ml300286h
• 作为产物：
  描述：

  4-甲氧基肉桂酸 在 氯化亚砜 、 溴 、 potassium carbonate 、 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.33h， 生成 5,7-dimethoxy-4-(4-methoxyphenyl)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of 4-arylcoumarin derivatives

  摘要：

  Two bioactive natural 4-arylcoumarins, 5,7,4'-trimethoxy-4-phenylcoumarin (1a), 5,7-dimethoxy-4-phenylcoumarin (1b) and five closely related derivatives 1c-g were synthesized. In vitro evaluation with a catechol subunit for antioxidant and antimicrobial activity, these compounds using standard methods showed that compounds id, if displayed promise radical scavenging activity and if was found to be the most active one against Bacillus dysenteriae. (C) 2010 Yong Zou. Published by Elsevier BAT. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.12.017

文献信息

• Synthesis of 4-arylcoumarins from Coutarea hexandra
  作者：G Monache

  DOI：10.1016/s0031-9422(00)81132-2

  日期：——

  Abstract The structures assigned to the 5,7-dimethoxy-4-arylcoumarins isolated from Coutarea hexandra have been confirmed by synthesis, via Pechmann condensation of phloroglucinol and an ethyl benzoylacetate derivative, the hydroxy groups of which were protected either by benzylation or by methylenedioxy group formation.

  摘要 从 Coutarea hexandra 中分离出的 5,7-二甲氧基-4-芳基香豆素的结构已通过间苯三酚和苯甲酰乙酸乙酯衍生物的 Pechmann 缩合合成得到证实，其羟基被苄基化或亚甲二氧基保护。形成。
• Synthesis of New Naturally Occurring 4-Phenyl-2<i>H</i>-1-benzopyran-2-ones
  作者：Virinder S. Parmar、Rajni Jain、Suddham Singh

  DOI：10.1246/bcsj.61.2277

  日期：1988.6

  5,7-Dimethoxy-4-(4-hydroxyphenyl)-2H-1-benzopyran-2-one and 5,7-dimethoxy-4-(4-methoxyphenyl)-2H-1-benzopyran-2-one, two new neoflavonoids occurring in Courtarea hexandra have been synthesized via Pechmann condensation. Attempts made to synthesize another 4-arylcoumarin, 5-hydroxy-7-methoxy-4-(2,5-dihydroxyphenyl)-2H-1-benzopyran-2-one, constituent of the same plant, led to the formation of the hitherto

  5,7-二甲氧基-4-(4-羟基苯基)-2H-1-苯并吡喃-2-one和5,7-二甲氧基-4-(4-甲氧基苯基)-2H-1-苯并吡喃-2-one，两个新的Courtarea hexandra 中的新黄酮类化合物是通过 Pechmann 缩合合成的。尝试合成另一种 4-芳基香豆素、5-羟基-7-甲氧基-4-(2,5-二羟基苯基)-2H-1-苯并吡喃-2-one，同一植物的成分，导致了迄今为止的形成未知 2-ethoxy-6-hydroxy-4H-1-benzopyran-4-one。
• Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
  作者：Maddali L.N. Rao、Abhijeet Kumar

  DOI：10.1016/j.tet.2014.07.059

  日期：2014.9

  4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2–4 h conditions

  在钯催化下，使用三芳基铋作为三重芳基化试剂，研究了不同取代的4-氯香豆素的交叉偶联反应。证明了4-氯香豆素的高反应性以化学选择性方式递送单芳基化和双芳基化产物。所采用的反应条件简单，稳定，并且在2-4小时的条件下，三芳基铋试剂的三重偶联反应性得到了良好的证明。在合成一些天然存在的新黄酮（3.27 – 3.30）中探索了该方法的实用性。另外，4-芳基香豆素3.1产物是制备（R）-托特罗定的有用前体。
• Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins
  作者：Gerard M. Boland、Dervilla M. X. Donnelly、Jean-Pierre Finet、Martin D. Rea

  DOI：10.1039/p19960002591

  日期：——

  Palladium-catalysed coupling of the 4-chloro- or 4-bromo-coumarins 1–4 with arylboronic acids 5–13 under the Suzuki reaction conditions constitutes an efficient access to 4-arylcoumarins. These 4-arylcoumarins can also be obtained in good yields (70–97%) by treatment of 4-trifluoromethyl-sulfonyloxycoumarins 35–38 with arylboronic acids under modified Suzuki reaction conditions, involving the use of copper(I) iodide as a co-catalyst.

  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。
• Synthesis and NMR of 4-Aryl-3,4-dihydrocoumarins and 4-Arylcoumarins
  作者：Jie Sun、Yanfeng Wang

  DOI：10.14233/ajchem.2014.17751

  日期：——

  This paper described the synthesis and 1H and 13C NMR chemical shifts of a series of 4-aryl-3,4-dihydrocoumarin and 4-arylcoumarin derivatives based on a combination of 1H and 13C NMR, HSQC and HMBC experiments.

  本文结合 1H 和 13C NMR、HSQC 和 HMBC 实验，描述了一系列 4-芳基-3,4-二氢香豆素和 4-芳基香豆素衍生物的合成以及 1H 和 13C NMR 化学位移。

表征谱图