2-Methyl-5,6-dihydrobenzo[h]chromen-4-one | 141582-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-Methyl-5,6-dihydrobenzo[h]chromen-4-one
• CAS: 141582-21-0
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: OVRIYGJVGGRBEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-5,6-dihydrobenzo[h]chromen-4-one 在 哌啶 、 吡啶 、 乙酸酐 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of new efficient laser dyes of red spectral range, the DCM analogs, based on 2-aryl-6-methyl-4H-pyrone

  摘要：

  A new method was developed for the synthesis of 2-aryl-6-methyl-4H-pyrones by the condensation of arylmethylketones with the acetoacetic ester ethylene ketal in the presence of sodium alkoxylate. New laser merocyanine dyes, the analogues of 4-dicyanomethylene-2-methyl-6-[(4-dimethylamino)styryl]-4H-pyran (DCM), were obtained based on the synthesized 2-aryl-4-pyrones. The dyes are characterized by high generation efficiency in the red spectral range.

  DOI：

  10.1134/s1070363211110156
• 作为产物：
  描述：

  苹果酯 、 3,4-二氢-1(2H)-萘酮 在 二苯并-18-冠醚-6 、 sodium 、 异丙醇 、 高氯酸 、 碳酸氢钠 作用下， 以 甲苯 、 水 为溶剂， 生成 2-Methyl-5,6-dihydrobenzo[h]chromen-4-one
  参考文献：
  名称：

  Synthesis of new efficient laser dyes of red spectral range, the DCM analogs, based on 2-aryl-6-methyl-4H-pyrone

  摘要：

  A new method was developed for the synthesis of 2-aryl-6-methyl-4H-pyrones by the condensation of arylmethylketones with the acetoacetic ester ethylene ketal in the presence of sodium alkoxylate. New laser merocyanine dyes, the analogues of 4-dicyanomethylene-2-methyl-6-[(4-dimethylamino)styryl]-4H-pyran (DCM), were obtained based on the synthesized 2-aryl-4-pyrones. The dyes are characterized by high generation efficiency in the red spectral range.

  DOI：

  10.1134/s1070363211110156

文献信息

• Rational design of novel near-infrared fluorescent DCM derivatives and their application in bioimaging
  作者：Xiaohang Wang、Zhiqian Guo、Shiqin Zhu、Yajing Liu、Ping Shi、He Tian、Wei-Hong Zhu

  DOI：10.1039/c6tb01096b

  日期：——

  The development of innovative strategies for high-performance near-infrared (NIR) fluorescent materials is in urgent demand for bioimaging. By replacing the stronger electron-withdrawing groups or extending the π-conjugated system, novel NIR fluorescent materials of DCM analogues have been developed, along with several striking characteristics: bright NIR fluorescence over 700 nm, large Stokes shift

  对于生物成像，迫切需要开发高性能近红外（NIR）荧光材料的创新策略。通过取代更强的吸电子基团或扩展π共轭体系，已开发出DCM类似物的新型NIR荧光材料，并具有一些引人注目的特性：700 nm以上的NIR荧光明亮，斯托克斯位移大，光稳定性好。已经证明，向DCM类似物的受体部分引入更强的吸电子单元是调整和延长具有大斯托克斯位移的发射波长并延长到NIR区域的有效有效的策略。与市售NIR染料ICG相比，S-DCM-N和S-DCM-P显示出优异的光稳定性和低光漂白性。
• Synthesis of new efficient laser dyes of red spectral range, the DCM analogs, based on 2-aryl-6-methyl-4H-pyrone
  作者：O. V. Ponomareva、A. P. Lugovskii、A. A. Lugovskii、M. P. Males、I. V. Komlev、E. E. Nifant’ev

  DOI：10.1134/s1070363211110156

  日期：2011.11

  A new method was developed for the synthesis of 2-aryl-6-methyl-4H-pyrones by the condensation of arylmethylketones with the acetoacetic ester ethylene ketal in the presence of sodium alkoxylate. New laser merocyanine dyes, the analogues of 4-dicyanomethylene-2-methyl-6-[(4-dimethylamino)styryl]-4H-pyran (DCM), were obtained based on the synthesized 2-aryl-4-pyrones. The dyes are characterized by high generation efficiency in the red spectral range.