7-(diethylamino)-3-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one | 1308287-74-2

• 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: 7-(diethylamino)-3-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one
• 英文别名: 7-(Diethylamino)-3-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]chromen-2-one
• CAS: 1308287-74-2
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: ILKAHBBECWEPDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(diethylamino)-3-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以45%的产率得到
  参考文献：
  名称：

  CO release with ratiometric fluorescence changes: a promising visible-light-triggered metal-free CO-releasing molecule

  摘要：

  报道了一种可见光触发的无金属二氧化碳释放分子，具有明显的比例荧光变化，用于在生物系统中释放二氧化碳。

  DOI：

  10.1039/c9cc04026a
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 2H-1-苯并吡喃-3-羧醛, 7-(二乙基氨基)-2-氧代- 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 7-(diethylamino)-3-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-2H-chromen-2-one
  参考文献：
  名称：

  A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism

  摘要：

  一种具有乙酰丙酮酸末端基团的香豆素查尔酮衍生物，基于脱保护、加成和随后的环化反应机理，作为一种比例荧光探针，用于检测肼。

  DOI：

  10.1039/c9cc08174g

文献信息

• One diethylamine coumarin derivative with nitro substituted chalcone structure as chemosensor for cyanide and copper ions
  作者：Yanyan Shan、Yunhui Sun、Ning Sun、Ruifang Guan、Duxia Cao、Kangnan Wang、Qianqian Wu、Yongxiao Xu

  DOI：10.1016/j.inoche.2015.06.031

  日期：2015.9

  Abstract One diethylamine coumarin derivative with nitro substituted chalcone structure was synthesized via typical condensation reaction between 4-nitro-2-(hydroxyl)acetophenone with 7-(diethylamino)coumarinaldehyde in good yields. The investigation indicated that the compound exhibits quickly obvious UV–vis absorption, color change and fluorescence response to cyanide and copper ions in acetonitrile

  摘要 通过4-硝基-2-(羟基)苯乙酮与7-(二乙氨基)香豆素醛的典型缩合反应，合成了一种具有硝基取代查尔酮结构的二乙胺香豆素衍生物。研究表明，该化合物在乙腈条件下对氰化物和铜离子表现出快速明显的紫外-可见吸收、颜色变化和荧光响应。基于光谱变化和原位 1 H NMR 的键合机制表明，氰化物键合到香豆素的 4 位，化合物和铜离子形式之间以 1:2 络合。
• ESIPT-based fluorescent enhanced probes prompted by methylated β-cyclodextrin for the detection of thiophenols
  作者：Hai-Yan Peng、Gang Zhang、Ru Sun、Yu-Jie Xu、Jian-Feng Ge

  DOI：10.1016/j.saa.2023.123012

  日期：2023.12

  Thiophenol and its derivatives are compounds with high toxicity to organisms and environmental pollution, so it is necessary to detect the level of thiophenols in the environment and biological samples. The probes 1a-b were obtained by introducing the 2,4-dinitrophenyl ether group into diethylcoumarin–salicylaldehyde based compounds. And they can form host-guest compounds with methylated β-cyclodextrin

  苯硫酚及其衍生物是对生物体具有高毒性并污染环境的化合物，因此有必要检测环境和生物样品中苯硫酚的含量。探针1a-b是通过将2,4-二硝基苯基醚基团引入二乙基香豆素-水杨醛基化合物中获得的。它们可以与甲基化β-环糊精(M-β-CD)形成主客体化合物，包合物的缔合常数分别为49.2 M -1、125 M -1。在苯硫酚检测中，探针1a-b在 600 nm ( 1a ) 和 670 nm ( 1b )处的荧光强度显着增加。同时，随着M-β-CD的加入，M-β-CD的疏水空腔显着提高了探针1a-b的荧光强度，从而使探针1a-b对苯硫酚的检测限从410 nM降低到365 nM。分别为 62 nM、33 nM。然而，在 M-β-CD 存在的情况下，探针1a-b对苯硫酚的良好选择性和短响应时间并未受到影响。此外，探针1a-b因其对苯硫酚的良好响应而被用于进一步的水样检测和HeLa细胞成像实验，结果表明探针
• Ratiometric Fluorescence Imaging of Cellular Glutathione
  作者：Gun-Joong Kim、Kiwon Lee、Hyockman Kwon、Hae-Jo Kim

  DOI：10.1021/ol200967w

  日期：2011.6.3

  A fluorescent probe (1) with a hydrogen bond was designed for the detection of GSH. The probe exhibited a rapid and ratiometric fluorescence response to GSH through a Michael reaction and allowed us to obtain clear cellular images for GSH.
• Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction
  作者：Hyun-Joon Ha、Doo-Ha Yoon、Seokan Park、Hae-Jo Kim

  DOI：10.1016/j.tet.2011.08.002

  日期：2011.10

  Weakly fluorescent coumarinyl enones are rapidly transformed into strongly fluorescent molecules through the Michael addition reaction of a thiol group, where an intramolecular hydrogen bond plays a critical role in the reaction rate. The molecular probe (3) with an ortho hydroxyl group to a carbonyl group exhibits a rapid response toward GSH owing to the stabilization of the possible oxyanion intermediate by a preferable intramolecular hydrogen bond. Probe 1 with an o-hydroxyl group also showed a moderately enhanced reaction rate with GSH and soluble in HEPES buffer to exhibit a highly selective and sensitive fluorescence turn-on response toward biothiols. (C) 2011 Elsevier Ltd. All rights reserved.