3-acetyl-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one | 910137-62-1

• 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-acetyl-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one
• 英文别名: 3-acetyl-7-(N,N-dimethylamino)-4-hydroxycoumarin；3-acetyl-7-N,N-dimethylamino-4-hydroxychromen-2-one；3-acetyl-7-dimethylamino-4-hydroxycoumarin；3-Acetyl-7-dimethylamino-4-hydroxycoumarin；3-acetyl-7-(dimethylamino)-4-hydroxychromen-2-one
• CAS: 910137-62-1
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: QTTIOEJMIUYDMB-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  482.2±45.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  3-acetyl-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one 在 哌啶 、 肼 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 3-(1-acetyl-5-(4-(dimethylamino)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis of 4-hydroxy-7-dimethylamino-3-pyrazolinylcoumarins and their polarity-sensitive properties

  摘要：

  Four 4-hydroxy-3-pyrazolinylcoumarin derivatives were synthesized and their UV-vis spectra in various compositions of MeOH and CH2Cl2 were measured. Among the prepared compounds, only one was found to exist mainly in the enol form in nonpolar solvents and the keto form in protic solvents, whereas the others are exclusively present in the enol forms regardless of solvent polarity. This polarity-sensitive property of 3-pyrazolinylcoumarins can be controlled by the electronic nature of the substituent at the 7-position of coumarin, the 1-position (nitrogen atom) of pyrazoline as well as the para-position of the benzene moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.142
• 作为产物：
  描述：

  7-(N,N-二甲氨基)-4-羟基香豆素 在 potassium cyanide 、 18-冠醚-6 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.5h， 生成 3-acetyl-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  三酮衍生物的结构，反应性及应用

  摘要：

  已经确定了有机和水溶液中几种三酮衍生物的主要互变异构体。它们对溶剂和碱的敏感特性已分别应用于极性敏感的荧光探针和酸性变色着色剂的设计中。还研究了2-酰基二酮，3-酰基-4-羟基香豆素和2-酰基-1,3-茚满二酮的区域选择性乙酰化和甲基化。结果表明，前两个的乙酰化和甲基化特别发生在环内烯醇氧处，而对于后者，它们发生在环外的烯醇氧处。

  DOI：

  10.1016/j.tet.2006.07.053

文献信息

• Design of a Coumarin-Based Triketone as a Fluorescent Protecting Group for Primary Amines
  作者：Pei-Yu Kuo、Ding-Yah Yang

  DOI：10.1021/jo801060p

  日期：2008.8.1

  A series of 3-acetyl-4-hydroxycoumarin and its derivatives were prepared and evaluated for their potential to function as a fluorescent primary amine protection group. When primary amines or amino acids react with the protecting group 3-acetyl-4-methoxy-7-N,N-dimethylaminocoumarin, the resulting compounds emit blue fluorescence with a quantum yield of 0.25-0.50 in methylene chloride. These protected compounds display satisfactory acid/base stability, and the protecting group can be removed with 5% hydrazine hydrate in DMF within 5 min at ambient temperature.
• Synthesis of Coumarin/Pyrrole-Fused Heterocycles and Their Photochemical and Redox-Switching Properties
  作者：Chi-Hui Lin、Ding-Yah Yang

  DOI：10.1021/ol401138q

  日期：2013.6.7

  Two coumarin/pyrrole-fused heterocycles were synthesized to investigate their photochemical and redox-switching properties. Photooxidation of the colorless diphenyl-substituted pyrrolocoumarin resulted in a distinct change to red and a sharp decrease in fluorescence Intensity. The photooxidized product can be swiftly reverted to the original form by NaCNBH3 reduction or hydrogenation.
• Structure, reactivity, and application of some triketone derivatives
  作者：You-Sheng Chen、Pei-Yu Kuo、Tien-Lan Shie、Ding-Yah Yang

  DOI：10.1016/j.tet.2006.07.053

  日期：2006.10

  The major tautomer of several triketone derivatives in organic and aqueous solutions has been determined. Their solvent- and base-sensitive properties have been applied in the design of a polarity-sensitive fluorescent probe and an acidichromic colorant, respectively. The regioselective acetylation and methylation of 2-acyldimedone, 3-acyl-4-hydroxycoumarin, and 2-acyl-1,3-indandione have also been

  已经确定了有机和水溶液中几种三酮衍生物的主要互变异构体。它们对溶剂和碱的敏感特性已分别应用于极性敏感的荧光探针和酸性变色着色剂的设计中。还研究了2-酰基二酮，3-酰基-4-羟基香豆素和2-酰基-1,3-茚满二酮的区域选择性乙酰化和甲基化。结果表明，前两个的乙酰化和甲基化特别发生在环内烯醇氧处，而对于后者，它们发生在环外的烯醇氧处。
• Synthesis of 4-hydroxy-7-dimethylamino-3-pyrazolinylcoumarins and their polarity-sensitive properties
  作者：Jiun-Han Lin、Chi-Hui Lin、Ding-Yah Yang

  DOI：10.1016/j.tetlet.2011.11.142

  日期：2012.2

  Four 4-hydroxy-3-pyrazolinylcoumarin derivatives were synthesized and their UV-vis spectra in various compositions of MeOH and CH2Cl2 were measured. Among the prepared compounds, only one was found to exist mainly in the enol form in nonpolar solvents and the keto form in protic solvents, whereas the others are exclusively present in the enol forms regardless of solvent polarity. This polarity-sensitive property of 3-pyrazolinylcoumarins can be controlled by the electronic nature of the substituent at the 7-position of coumarin, the 1-position (nitrogen atom) of pyrazoline as well as the para-position of the benzene moiety. (C) 2011 Elsevier Ltd. All rights reserved.