4-(aminomethyl)-7-(diethylamino)-2H-chromen-2-one

• 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: 4-(aminomethyl)-7-(diethylamino)-2H-chromen-2-one
• 英文别名: 4-Aminomethyl-7-diethylaminocoumarin；4-(aminomethyl)-7-(diethylamino)chromen-2-one
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: PKWWNQRNINIDEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(aminomethyl)-7-(diethylamino)-2H-chromen-2-one 、 五氟苯甲酰氯 生成 7-diethylamino-4-(((pentafluorobenzoyl)amino)methyl)coumarin
  参考文献：
  名称：

  Assay for glutathiane transferase using polyhaloaryl-substituted

  摘要：

  本发明涉及含有多卤芳基团的化合物。该发明的化合物特别适用于测定多种酶，包括细胞内酶。本发明还描述了对谷胱甘肽和/或谷胱甘肽转移酶酶的测定。本发明的部分化合物特别适用于提高细胞内酶代谢产物的荧光产物的保留。

  公开号：

  US05773236A1
• 作为产物：
  描述：

  7-二乙氨基-4-甲基香豆素 在 吡啶 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 sodium azide 、 palladium on activated charcoal 、 氢气 、 对甲苯磺酰氯 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 4-(aminomethyl)-7-(diethylamino)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis, Photophysical, Photochemical, and Computational Studies of Coumarin-Labeled Nicotinamide Derivatives

  摘要：

  The syntheses and photophysical/photochemical properties of two amide-tethered coumarin-labeled nicotinamides are described. Photochemical studies of 6-bromo-7-hydroxycoumarin-4-ylmethylnicotinamide (BHC-nicotinamide) revealed an unexpected solvent effect. This result is rationalized by computational studies of the different protonation states using TD-DFT with the M06L/6-311+G** method with implicit and explicit solvation models. Molecular orbital energies responsible for the lambda(max) excitation show that the functionalization of the coumarin ring results in a strong red-shift from 330 to 370 nm when the pH of solution is increased from 3.06 to 8.07. From this MO analysis, a model for solvent interactions has been proposed. The BHC-nicotinamide proved to be photochemically stable, which is also interpreted in terms of NBO calculations. The results provide a set of principles for the rational design of either photostable labeling reagents or photolabile cage compounds.

  DOI：

  10.1021/jo2025527

文献信息

• The Aryne Phosphate Reaction**
  作者：Thomas M. Haas、Stefan Wiesler、Tobias Dürr‐Mayer、Alexander Ripp、Paraskevi Fouka、Danye Qiu、Henning J. Jessen

  DOI：10.1002/anie.202113231

  日期：2022.1.3

  The ability of phosphates to act as efficient arynophiles is demonstrated. The resulting aryne phosphate reaction is a versatile tool for arene phosphorylation or phosphate arylation. A broad scope of variously arylated phosphate products is culminating in novel nucleotide analogues and a benchmarking octaphosphorylation.

  证明了磷酸盐作为有效嗜亲菌的能力。由此产生的芳基磷酸酯反应是芳烃磷酸化或磷酸酯芳基化的通用工具。各种芳基化磷酸盐产品的范围广泛，最终形成了新型核苷酸类似物和基准八磷酸化。
• US5773236A
  申请人：——

  公开号：US5773236A

  公开（公告）日：1998-06-30
• Assay for glutathiane transferase using polyhaloaryl-substituted
  申请人：Molecule Probes, Inc.

  公开号：US05773236A1

  公开（公告）日：1998-06-30

  The subject invention describes compounds containing a polyhalogenated aryl moiety. The compounds of the invention are particularly useful for the assay of a variety of enzymes, including intracellular enzymes. The subject invention also describes assays for glutathione and/or glutathione transferase enzymes. Selected compounds of the invention are particularly useful for improving the retention of fluorescent products of enzyme metabolism in cells.

  本发明涉及含有多卤芳基团的化合物。该发明的化合物特别适用于测定多种酶，包括细胞内酶。本发明还描述了对谷胱甘肽和/或谷胱甘肽转移酶酶的测定。本发明的部分化合物特别适用于提高细胞内酶代谢产物的荧光产物的保留。
• Synthesis, Photophysical, Photochemical, and Computational Studies of Coumarin-Labeled Nicotinamide Derivatives
  作者：Pauline Bourbon、Qian Peng、Guillermo Ferraudi、Cynthia Stauffacher、Olaf Wiest、Paul Helquist

  DOI：10.1021/jo2025527

  日期：2012.3.16

  The syntheses and photophysical/photochemical properties of two amide-tethered coumarin-labeled nicotinamides are described. Photochemical studies of 6-bromo-7-hydroxycoumarin-4-ylmethylnicotinamide (BHC-nicotinamide) revealed an unexpected solvent effect. This result is rationalized by computational studies of the different protonation states using TD-DFT with the M06L/6-311+G** method with implicit and explicit solvation models. Molecular orbital energies responsible for the lambda(max) excitation show that the functionalization of the coumarin ring results in a strong red-shift from 330 to 370 nm when the pH of solution is increased from 3.06 to 8.07. From this MO analysis, a model for solvent interactions has been proposed. The BHC-nicotinamide proved to be photochemically stable, which is also interpreted in terms of NBO calculations. The results provide a set of principles for the rational design of either photostable labeling reagents or photolabile cage compounds.