7-hydroxy-8-((phenylamino)methyl)-4-methylcoumarin | 93316-25-7

• 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-hydroxy-8-((phenylamino)methyl)-4-methylcoumarin
• 英文别名: 7-Hydroxy-4-methyl-8--cumarin；8-anilinomethyl-7-hydroxy-4-methyl-chromen-2-one；8-(Anilinomethyl)-7-hydroxy-4-methylchromen-2-one；8-(anilinomethyl)-7-hydroxy-4-methylchromen-2-one
• CAS: 93316-25-7
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: AZUIWQFIPLBSHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 7-hydroxy-8-((phenylamino)methyl)-4-methylcoumarin 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 4-methyl-9-phenyl-9,10-dihydro-2H,8H-chromeno[8,7-E][1,3]oxazin-2-one
  参考文献：
  名称：

  Mannich Reaction with Hydroxycoumarins¹

  摘要：

  DOI：

  10.1021/jo01070a543
• 作为产物：
  描述：

  8-formyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one 在 sodium tetrahydroborate 、 乙醇 作用下， 以 四氢呋喃 为溶剂， 以78.5%的产率得到7-hydroxy-8-((phenylamino)methyl)-4-methylcoumarin
  参考文献：
  名称：

  Hydrogen bond induced fluorescence recovery of coumarin-based sensor system

  摘要：

  Two coumarin-type fluorescent sensors were synthesized and their fluorescence response to pH value was investigated. The fluorescence intensity of sensor 3 and sensor 4 is obviously enhanced along with the increase of pH from 7 to 12 and the reduction of pH value from 8 to 1, respectively. Possible mechanism for these fluorescence recovery systems is proposed. Intramolecular hydrogen bond could be formed under different condition, which blocks electron transferring route from nitrogen atom to fluorophore. The blue fluorescence color change of the two sensory systems could be directly detected by naked eyes under UV-lamp for pH values. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.034

文献信息

• Mannich Reaction with Hydroxycoumarins¹
  作者：R. B. Desai

  DOI：10.1021/jo01070a543

  日期：1961.12
• Hydrogen bond induced fluorescence recovery of coumarin-based sensor system
  作者：Xiaobo Huang、Yu Dong、Qianwen Huang、Yixiang Cheng

  DOI：10.1016/j.tetlet.2013.05.034

  日期：2013.7

  Two coumarin-type fluorescent sensors were synthesized and their fluorescence response to pH value was investigated. The fluorescence intensity of sensor 3 and sensor 4 is obviously enhanced along with the increase of pH from 7 to 12 and the reduction of pH value from 8 to 1, respectively. Possible mechanism for these fluorescence recovery systems is proposed. Intramolecular hydrogen bond could be formed under different condition, which blocks electron transferring route from nitrogen atom to fluorophore. The blue fluorescence color change of the two sensory systems could be directly detected by naked eyes under UV-lamp for pH values. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.