7-methoxy-3-(p-tolyl)-2H-chromen-2-one | 20050-72-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-methoxy-3-(p-tolyl)-2H-chromen-2-one
• 英文别名: 7-Methoxy-3-(4-methylphenyl)chromen-2-one；7-methoxy-3-(4-methylphenyl)chromen-2-one
• CAS: 20050-72-0
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: NLELIZFMMXMRIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  7-methoxy-3-(p-tolyl)-2H-chromen-2-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 21.0h， 生成 3-{4-[(Benzylmethylamino)methyl]phenyl}-7-methoxychromen-2-one
  参考文献：
  名称：

  Extensive SAR and Computational Studies of 3-{4-[(Benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) Derivatives

  摘要：

  AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-beta pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced A beta-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.

  DOI：

  10.1021/jm070100g
• 作为产物：
  描述：

  对甲基苯乙酸 在 potassium carbonate 、 三乙胺 作用下， 以 乙酸酐 、 乙腈 为溶剂， 反应 12.0h， 生成 7-methoxy-3-(p-tolyl)-2H-chromen-2-one
  参考文献：
  名称：

  轻度扭曲的香豆素分子的合理设计，具有出色的溶液和坚固的双重高效发光

  摘要：

  赋予在溶液和固态中都高度发射的轻微扭曲的分子对于理解使发光体的发光效率最大化的原理非常重要。为此，合成了在7位具有不同烷氧基取代基的一系列轻微扭曲的香豆素发光体CM s。研究了替代物对四种化合物在溶液，THF / H 2 O混合物和固态中的多样性光物理性质的影响。与参考化合物CM（3- p-tolyl-2H-chromen-2-one）的引入，即引入的富含电子的烷氧基取代基不但没有增强分子内电荷转移（ICT）的作用，而且还显着改变了其在晶体中的分子堆积模式。增加辐射和抑制非辐射路径的综合效果同时提高了溶液和固态中CM1 - CM3的发光效率。最终，具有乙氧基取代基的化合物CM2表现出最强的蓝色发射，在溶液和固态下的荧光量子产率分别高达73.2％和96.7％。这项工作提出了解决方案在固态和固态的双重强荧光发光体的有效策略。

  DOI：

  10.1016/j.dyepig.2017.09.060

文献信息

• Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions
  作者：Parul Chauhan、Makthala Ravi、Shikha Singh、Prashant Prajapati、Prem P. Yadav

  DOI：10.1039/c5ra20954d

  日期：——

  A transition-metal-free regioselective α-arylation of coumarins and 2-pyridones has been accomplished by the reaction of phenylhydrazines with coumarins or 2-pyridones.

  一种无过渡金属的选择性α-芳基化反应已经成功实现，通过苯基肼与香豆素或2-吡啶酮的反应。
• A Complete Switch of the Directional Selectivity in the Annulation of 2-Hydroxybenzaldehydes with Alkynes
  作者：Huiying Zeng、Chao-Jun Li

  DOI：10.1002/anie.201407589

  日期：2014.12.8

  reaction selectivity is an eternal pursuit for chemists working in chemical synthesis. As part of this endeavor, our group has been exploring the possibility of constructing different natural product skeletons from the same simple starting materials by using different catalytic systems. In our previous work, an isoflavanone skeleton was obtained from the annulation of a salicylaldehyde and an alkyne

  控制反应选择性是从事化学合成工作的化学家们永恒的追求。作为这项工作的一部分，我们的小组一直在探索通过使用不同的催化体系，从相同的简单起始原料构建不同的天然产物骨架的可能性。在我们以前的工作中，当使用金催化剂时，通过水杨醛和炔烃的环化获得了异黄烷酮骨架。在本文中，显示了通过与相同的起始原料即末端炔烃和水杨醛进行环化反应，只需切换为铑催化剂，即可有效地获得香豆素骨架。基于同位素替代实验，提出了一种合理的反应机理，用于这种新的环空反应。
• Palladium catalyzed dehydrogenative arylation of coumarins: an unexpected switch in regioselectivity
  作者：Farnaz Jafarpour、Hamideh Hazrati、Nazanin Mohasselyazdi、Mehdi Khoobi、Abbas Shafiee

  DOI：10.1039/c3cc46959j

  日期：——

  A new regioselective alpha-arylation of coumarins with unactivated simple arenes via a palladium-catalyzed twofold C-H functionalization is devised. This method offers an attractive new approach to synthesis of a wide variety of 3-arylcoumarins from readily accessible starting materials.

  设计了一种新的香豆素的区域选择性α-芳构化与未活化的简单芳烃，其通过钯催化的双CH官能团化。该方法提供了一种有吸引力的新方法，可以从易于获得的起始原料合成多种3-芳基香豆素。
• Through‐Bond Energy Transfer Cassettes with Minimal Spectral Overlap between the Donor Emission and Acceptor Absorption: Coumarin–Rhodamine Dyads with Large Pseudo‐Stokes Shifts and Emission Shifts
  作者：Weiying Lin、Lin Yuan、Zengmei Cao、Yanming Feng、Jizeng Song

  DOI：10.1002/anie.200904515

  日期：2010.1.8

  Cassette recording: A new class of coumarin–rhodamine through‐bond energy‐transfer (TBET) cassettes with minimal spectral overlap between the donor emission and the acceptor absorption (see picture) show large pseudo‐Stokes shifts (up to 230 nm) and emission shifts (up to 170 nm). The utility of this TBET platform for TBET‐based probe development was demonstrated by a new ratiometric fluorescence pH

  盒式磁带记录：新型香豆素-若丹明通过键能量转移（TBET）盒带，在供体发射和受体吸收之间的光谱重叠最小（参见图片），显示出大的伪斯托克斯位移（最大230 nm）和发射位移（最大170 nm）。新型比例荧光pH探针证明了该TBET平台在基于TBET的探针开发中的实用性。
• Highly Regioselective α-Arylation of Coumarins<i>via</i>Palladium-Catalyzed CH Activation/Desulfitative Coupling
  作者：Farnaz Jafarpour、Mina Barzegar Amiri Olia、Hamideh Hazrati

  DOI：10.1002/adsc.201300707

  日期：2013.11.25

  AbstractA novel regioselective α‐arylation of coumarins with readily available arenesulfonyl chlorides and sodium arenesulfinates via palladium‐catalyzed direct CH functionalizations under mild reaction conditions is described. This protocol presents an unexpected and highly regio‐controlled arylation of coumarins at C‐3 to construct interesting 3‐arylcoumarins with fascinating biological and fluorescent properties. The regioselectivity observed is in sharp contrast with that expected for the Heck reactions.magnified image