3-benzoyl-7-N,N-dimethylamino-4-hydroxychromen-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-7-N,N-dimethylamino-4-hydroxychromen-2-one
• 英文别名: 3-Benzoyl-7-dimethylamino-4-hydroxycoumarin；3-benzoyl-7-(dimethylamino)-4-hydroxychromen-2-one
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: QGDADJQQSOXVAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-benzoyl-7-N,N-dimethylamino-4-hydroxychromen-2-one 在 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以70%的产率得到3-benzoyl-7-N,N-dimethylamino-4-chlorochromen-2-one
  参考文献：
  名称：

  Synthesis of Coumarin/Pyrrole-Fused Heterocycles and Their Photochemical and Redox-Switching Properties

  摘要：

  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.

  DOI：

  10.1021/ol401138q

文献信息

• 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。
• Conformation and photochemical properties of 3-benzoyl-4-benzylamino-7-dimethylaminocoumarin
  作者：Chi-Hui Lin、Rong-Ren Chuang、Pei-Yu Kuo、Ding-Yah Yang

  DOI：10.1016/j.tetlet.2013.03.016

  日期：2013.5

  3-Benzoyl-4-benzylamino-7-dimethylaminocoumarin was synthesized and its conformation in solid state and solution was determined. While the X-ray crystal analysis showed an aromatic pi-pi stacking interaction in the solid state, the proton NMR studies suggested the presence of an intramolecular hydrogen bonding in solution. Adjacent functional group modifications through N-methylation, reduction of carbonyl group, or replacing the coumarin moiety to dimedone, all resulted in disrupting the pi-pi stacking conformation. Upon UV irradiation, the 7-methylamino group can be oxidized by molecular oxygen to the corresponding formamide in the absence of any external photosensitizers. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.