3-(2-azidoacetyl)-7-(diethylamino)-2H-chromen-2-one | 321354-94-3

• 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: 3-(2-azidoacetyl)-7-(diethylamino)-2H-chromen-2-one
• 英文别名: 3-(2-azidoacetyl)-7-diethylamino-2H-chromen-2-one；3-(2-Azidoacetyl)-7-(diethylamino)chromen-2-one
• CAS: 321354-94-3
• 化学式: C₁₅H₁₆N₄O₃
• 分子量: 300.317
• InChiKey: QFVPDLBPMOOREP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异烟酸酰氯 、 3-(2-azidoacetyl)-7-(diethylamino)-2H-chromen-2-one 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 7-(diethylamino)-3-(2-(pyridin-4-yl)oxazol-5-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and fluorescence properties of environment-sensitive 7-(diethylamino)coumarin derivatives

  摘要：

  By linking 7-(diethylamino)coumarin and different aromatic groups via an oxazole moiety, a small series of new environment-sensitive fluorophores have been synthesized. They display varying degrees of environment-sensitivity, depending on the aromatic group present on the oxazole ring. Additionally, these coumarin-based fluorophores show considerably better photostability compared to the nitrobenzoxadiazole fluorophore, and offer a good starting point for the further development of these fluorophores into environment-sensitive membrane probes or for other applications requiring sensitivity to the environment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.019
• 作为产物：
  描述：

  3-乙酰基-7-二乙基氨基-2H-色烯-2-酮 在 sodium azide 、 tetra-N-butylammonium tribromide 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 3-(2-azidoacetyl)-7-(diethylamino)-2H-chromen-2-one
  参考文献：
  名称：

  Fluorescent Labeling Reagents. Part 3. Screening Search for Organic Fluorophores: Syntheses and Fluorescence Properties of 3-Azolyl-7-diethylaminocoumarin Derivatives.

  摘要：

  为了寻找高度敏感的荧光探针，合成了3-杂唑基-7-二乙氨基香豆素衍生物。这些香豆素-噻唑化合物的吸收和荧光最大值均表现出红移，相比于相应的香豆素-噁唑化合物，其摩尔吸光度和荧光强度均有所增加。其中，3-(5-乙氧基羧基-1, 3-噻唑-2-基)-7-二乙氨基-2H-香豆素-2-酮（3e）是作为分析用途的荧光探针中最有前途的候选者之一，适用于分析化学和生物化学领域。

  DOI：

  10.1248/cpb.48.1702

文献信息

• Fluorescent Labeling Reagents. Part 3. Screening Search for Organic Fluorophores: Syntheses and Fluorescence Properties of 3-Azolyl-7-diethylaminocoumarin Derivatives.
  作者：Haruko TAKECHI、Yoshiyuki ODA、Naozumi NISHIZONO、Kazuaki ODA、Minoru MACHIDA

  DOI：10.1248/cpb.48.1702

  日期：——

  In order to find a highly sensitive fluorophore, 3-azolyl-7-diethylaminocoumarin derivatives were synthesized. Both the absorption and fluorescence maxima of the coumarin-thiazole compounds showed red shifts with increases of the molar absorptivities and fluorescence intensities, in comparison with those of the corresponding coumarin-oxazole compounds. Among them, 3-(5-ethoxycarbonyl-1, 3-thiazol-2-yl)-7-diethylamino-2H-chromen-2-one (3e) was one of the most promising candidates as a fluorophore accessible for analytical purposes in the fields of analytical and biological chemistry.

  为了寻找高度敏感的荧光探针，合成了3-杂唑基-7-二乙氨基香豆素衍生物。这些香豆素-噻唑化合物的吸收和荧光最大值均表现出红移，相比于相应的香豆素-噁唑化合物，其摩尔吸光度和荧光强度均有所增加。其中，3-(5-乙氧基羧基-1, 3-噻唑-2-基)-7-二乙氨基-2H-香豆素-2-酮（3e）是作为分析用途的荧光探针中最有前途的候选者之一，适用于分析化学和生物化学领域。
• An investigation into the synthesis of azido-functionalised coumarins for application in 1,3-dipolar “click” cycloaddition reactions
  作者：Vikki Evans、Philip Duncanson、Majid Motevalli、Michael Watkinson

  DOI：10.1016/j.dyepig.2016.06.028

  日期：2016.12

  been assessed for the synthesis of two coumarin fluorophores containing azides, 1a and 2, for subsequent “click” modification. In the case of 1a reported methods were successfully applied, but the resulting azide proved to be rather unstable and appears more suited to in-situ generation and conversion to the “click” triazole. In the case of 2, reported methods for the synthesis of precursor 5 were ineffective

  已经评估了一系列报道的方法，用于合成两个含有叠氮化物1a和2的香豆素荧光团，用于随后的“点击”修饰。在1a的情况下，已成功应用了报道的方法，但事实证明生成的叠氮化物相当不稳定，并且似乎更适合原位生成和转化为“喀哒”三唑。在2的情况下，已报道的合成前体5的方法在两种情况下均无效，并且导致没有将溴化为羰基的溴化反应或形成了多种不需要的副产物，其中一些被分离出来，为6-13。过量使用CuBr 2或Br2在50％的HBr在乙酸中的隔离确实结果5，其可以被有效地转化成2使用过量的NaN 3的THF溶液。
• Synthesis and fluorescence properties of environment-sensitive 7-(diethylamino)coumarin derivatives
  作者：Stane Pajk

  DOI：10.1016/j.tetlet.2014.09.019

  日期：2014.10

  By linking 7-(diethylamino)coumarin and different aromatic groups via an oxazole moiety, a small series of new environment-sensitive fluorophores have been synthesized. They display varying degrees of environment-sensitivity, depending on the aromatic group present on the oxazole ring. Additionally, these coumarin-based fluorophores show considerably better photostability compared to the nitrobenzoxadiazole fluorophore, and offer a good starting point for the further development of these fluorophores into environment-sensitive membrane probes or for other applications requiring sensitivity to the environment. (C) 2014 Elsevier Ltd. All rights reserved.