methyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate

• 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: methyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
• 英文别名: methyl 3-[7-(diethylamino)-2-oxo-2H-chromen-3-yl]-3-oxopropanoate；methyl 3-(7-diethylamino-2-oxo-2H-chromen-3-yl)-3-oxopropanoate；methyl 3-(7-diethylamino-2-oxo-2H-chromen-3-yl)-3-oxopropionate；Methyl 7-diethylamino-3coumarinoylacetate；methyl 3-[7-(diethylamino)-2-oxochromen-3-yl]-3-oxopropanoate
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: NGZOTIQHWZXUDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 以86%的产率得到3-(7-(N,N-diethylamino)-2-oxo-2H-chromen-3-yl)-1,2-dihydropyrazol-5-one
  参考文献：
  名称：

  A novel fluorescence turn-on coumarin-pyrazolone based monomethine probe for biothiol detection

  摘要：

  A coumarin-pyrazolone monomethine based turn-on fluorescence ratiometric probe C-3 for selective detection of cysteine (Cys) and glutathione (GSH) is reported. It exhibits OFF-ON states and is more sensitive to GSH in aqueous solution neutral and basic pH. The ON state is due to the inhibition of intramolecular charge transfer (ICT) process between pyrrole and pyrazolone moieties. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.06.008
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 4-(二乙氨基)水杨醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 methyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
  参考文献：
  名称：

  脯氨酸在超声辐射下催化四组分一锅合成含香豆素的二氢吡喃并[2,3- c ]吡唑

  摘要：

  一种简便的方法来含香豆素的二氢吡喃并[2,3-的合成Ç ]吡唑通过β二羰基化合物，苯肼，芳香醛和丙二腈在EtOH的四组分反应催化的通过升超声波照射下脯氨酸被描述。该反应在室温下以良好或优异的产率得到了包含香豆素的二氢吡喃并[2,3- c ]吡唑。该方法具有许多优点，例如反应时间更短，环境友好，后处理步骤简单和产率更高。

  DOI：

  10.1016/j.tet.2016.10.016

文献信息

• Corroles bearing diverse coumarin units — synthesis and optical properties
  作者：Mariusz Tasior、Roman Voloshchuk、Yevgen M. Poronik、Tomasz Rowicki、Daniel T. Gryko

  DOI：10.1142/s1088424611003926

  日期：2011.9

  Two strategies were shown to be efficient in the construction of corroles with appended coumarin units. Direct condensation of formyl-coumarins with dipyrromethanes leads to a diverse range of trans-A₂B-corroles in moderate yields. We showed that the strategy consisting of synthesis of various hydroxycoumarins followed by nucleophilic aromatic substitution with pentafluorobenzaldehyde and subsequent condensation of the resulting coumarin-aldehyde with dipyrromethanes is the most general methodology for the preparation of such dyads. The second, more demanding but also more efficient approach is based on Sonogashira coupling of ethynylphenylcorroles with suitably functionalized bromocoumarins. A broad range of structurally diverse coumarins were employed with absorption ranging from 300 to 460 nm. Spectroscopic properties of all eight dyads studied suggest that the linker components are weakly electronically coupled.

  研究表明，有两种方法可以有效地构建带有香豆素单元的络合物。甲酰基香豆素与二吡咯烷的直接缩合可产生多种反式-A2B-络合物，产率适中。我们的研究表明，先合成各种羟基香豆素，再用五氟苯甲醛进行亲核芳香取代，然后将得到的香豆素醛与二吡咯烷缩合，这种策略是制备此类二元化合物的最通用方法。第二种方法要求更高，但也更有效，它是基于乙炔基苯甲酰与适当官能化的溴香豆素的 Sonogashira 偶联。我们采用了多种结构不同的香豆素，它们的吸收范围在 300 纳米到 460 纳米之间。所研究的全部八种二元化合物的光谱特性表明，连接体成分是弱电子耦合的。
• l -Proline catalyzed four-component one-pot synthesis of coumarin-containing dihydropyrano[2,3- c ]pyrazoles under ultrasonic irradiation
  作者：Mengnisa Seydimemet、Keyume Ablajan、Mawjvda Hamdulla、Wenbo Li、Adil Omar、Mamateli Obul

  DOI：10.1016/j.tet.2016.10.016

  日期：2016.11

  A simple and convenient approach to the synthesis of coumarin-containing dihydropyrano[2,3-c]pyrazoles via four-component reaction of β-dicarbonyl compound, phenylhydrazine, aromatic aldehydes and malononitrile in EtOH catalyzed by l-proline under ultrasonic irradiation is described. The reaction gives the coumarin-containing dihydropyrano[2,3-c]pyrazoles in good to excellent yields at room temperature

  一种简便的方法来含香豆素的二氢吡喃并[2,3-的合成Ç ]吡唑通过β二羰基化合物，苯肼，芳香醛和丙二腈在EtOH的四组分反应催化的通过升超声波照射下脯氨酸被描述。该反应在室温下以良好或优异的产率得到了包含香豆素的二氢吡喃并[2,3- c ]吡唑。该方法具有许多优点，例如反应时间更短，环境友好，后处理步骤简单和产率更高。
• <i>Trans</i>-A₂B-corroles Bearing a Coumarin Moiety - From Synthesis to Photophysics
  作者：Mariusz Tasior、Daniel T. Gryko、Dominika J. Pielacińska、Alberto Zanelli、Lucia Flamigni

  DOI：10.1002/asia.200900345

  日期：2010.1.4

  transfer from the coumarin moiety to corrole in all four dyads. Energy transfer can be clearly ascribed to a dipole–dipole mechanism (Förster) for all dyads that contain luminescent coumarins and to an electron exchange mechanism (Dexter) for the dyad with the non‐luminescent one. In the case of the dyad that bears coumarin with a hydroxy group at position 5, an electron‐transfer was detected from corrole

  合成了由corrole和香豆素单元组成的四个二元组。合成了三种香豆素甲醛并将其转化为相应的反式-A 2B-与5-（五氟苯基）二吡咯甲烷反应而发生腐蚀。业已证明，这种直接缩合可以以中等收率产生相应的腐蚀。羟基苯甲醛与乙烯基phosph盐的反应已被认为是制备具有各种取代基样式的甲酰基香豆素的最通用方法。通过Sonogashira偶联合成了由酮双香豆素和甲氧基组成的二元组。光谱和光物理研究表明，在所有四个二元组中，香豆素部分都有效转移了能量。对于所有包含发光香豆素的二元组，能量转移可以明确地归因于偶极-偶极机制（Förster），对于不发光的二元组，其能量交换可以归因于电子交换机制（Dexter）。对于在5位带有羟基香豆素的二元组，检测到电子从腐蚀物向香豆素转移。后一种方法是可能的，因为这种香豆素的还原电位适当地低。
• Light-sensitive compositions with 3-substituted coumarin compounds as
  申请人：Eastman Kodak Company

  公开号：US04147552A1

  公开（公告）日：1979-04-03

  3-Substituted coumarins are efficient sensitizers for light-sensitive unsaturated materials such as unsaturated vesiculators which release a gas upon exposure to radiation, unsaturated monomers and photocrosslinkable unsaturated polymers, and azides such as photocrosslinkable polymeric azides used in photomechanical resists and lithographic plates. Water soluble derivatives can be used for aqueous coatable or aqueous processable systems.

  3-取代香豆素是光敏不饱和材料的有效增感剂，例如不饱和泡沫剂，在辐射下释放气体，不饱和单体和光交联不饱和聚合物，以及偶氮化物，例如用于光机械抗蚀剂和印刷版的光交联聚合偶氮化物。水溶性衍生物可用于水可涂覆或水可处理系统。
• H-bond stabilization of a tautomeric coumarin-pyrazole-pyridine triad generates a PET driven, reversible and reusable fluorescent chemosensor for anion detection
  作者：Meltem Alkış、Damla Pekyılmaz、Ergin Yalçın、Burcu Aydıner、Yavuz Dede、Zeynel Seferoğlu

  DOI：10.1016/j.dyepig.2017.03.011

  日期：2017.6

  A coumarin based anion sensor utilizing pyrazole both as an electron donor and hydroxyl H-bond donor and pyridine as a tautomer stabilizer is reported. The chemosensor exhibits ON-OFF-ON states and is more sensitive to F- at the stoichiometric ratio of 1:1. The OFF state is due to PET and the role of pyrazole is two fold, both stabilization of the enol tautomer via H-bonding and hosting domain of electrons enabling PET. Moreover, the absorption and emission properties of chemosensor change drastically upon acidification. (C) 2017 Elsevier Ltd. All rights reserved.