3-acetyl-7-(N,N-dimethylamino)-4-methoxychromen-2-one | 1043892-97-2

• 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-(N,N-dimethylamino)-4-methoxychromen-2-one
• 英文别名: 3-Acetyl-7-(dimethylamino)-4-methoxychromen-2-one；3-acetyl-7-(dimethylamino)-4-methoxychromen-2-one
• CAS: 1043892-97-2
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: YYJBTFPHHVLLFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-7-(N,N-dimethylamino)-4-methoxychromen-2-one 在 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 3-acetyl-7-(dimethylamino)-3-methyl-2-phenyl-3,3a-dihydrochromeno[4,3-b]pyrrol-4(9bH)-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
• 作为产物：
  描述：

  重氮甲烷 、 3-acetyl-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到3-acetyl-7-(N,N-dimethylamino)-4-methoxychromen-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

• 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.