3-(3,4-dimethyl-pyrrol-2-yl)-propionic acid ethyl ester | 62371-11-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(3,4-dimethyl-pyrrol-2-yl)-propionic acid ethyl ester
• 英文别名: Ethyl 3-(3,4-dimethyl-1H-pyrrol-2-yl)propanoate
• CAS: 62371-11-3
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: PCEBKXNMPAZGHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟化硼乙醚 、 3-(3,4-dimethyl-pyrrol-2-yl)-propionic acid ethyl ester 、 (3,5-dimethyl-1H-pyrrol-2-yl)(2-fluorophenyl)methanone 在 三氯氧磷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以30 %的产率得到ethyl 3-(5,5-difluoro-10-(2-fluorophenyl)-1,2,7,9-tetramethyl-5H-5λ4,6λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-3-yl)propanoate
  参考文献：
  名称：

  Chemical Control of Fluorescence Lifetime towards Multiplexing Imaging

  摘要：

  Fluorescence lifetime imaging has been a powerful tool for biomedical research. Recently, fluorescence lifetime‐based multiplexing imaging has expanded imaging channels by using probes that harbor the same spectral channels and distinct excited state lifetime. While it is desirable to control the excited state lifetime of any given fluorescent probes, the rational control of fluorescence lifetimes remains a challenge. Herein, we chose boron dipyrromethene (BODIPY) as a model system and provided chemical strategies to regulate the fluorescence lifetime of its derivatives with varying spectral features. We find electronegativity of structural substituents at the 8’ and 5’ positions are important to control the lifetime for the green‐emitting and red‐emitting BODIPY scaffolds. Mechanistically, such influences are exerted via the photo‐induced electron transfer and the intramolecular charge transfer processes for the 8’ and 5’ positions of BODIPY, respectively. Based on these principles, we have generated a group of BODIPY probes that enable imaging experiments to separate multiple targets using fluorescence lifetime as a signal. In addition to BODIPY, we envision modulation of electronegativity of chemical substituents could serve as a feasible strategy to achieve rational control of fluorescence lifetime for a variety of small molecule fluorophores.

  DOI：

  10.1002/anie.202403029

文献信息

• Chemical Control of Fluorescence Lifetime towards Multiplexing Imaging
  作者：Junbao Ma、Feng Luo、Chia-Heng Hsiung、Jianan Dai、Zizhu Tan、Songtao Ye、Lina Ding、Baoxing Shen、Xin Zhang

  DOI：10.1002/anie.202403029

  日期：——

  Fluorescence lifetime imaging has been a powerful tool for biomedical research. Recently, fluorescence lifetime‐based multiplexing imaging has expanded imaging channels by using probes that harbor the same spectral channels and distinct excited state lifetime. While it is desirable to control the excited state lifetime of any given fluorescent probes, the rational control of fluorescence lifetimes remains a challenge. Herein, we chose boron dipyrromethene (BODIPY) as a model system and provided chemical strategies to regulate the fluorescence lifetime of its derivatives with varying spectral features. We find electronegativity of structural substituents at the 8’ and 5’ positions are important to control the lifetime for the green‐emitting and red‐emitting BODIPY scaffolds. Mechanistically, such influences are exerted via the photo‐induced electron transfer and the intramolecular charge transfer processes for the 8’ and 5’ positions of BODIPY, respectively. Based on these principles, we have generated a group of BODIPY probes that enable imaging experiments to separate multiple targets using fluorescence lifetime as a signal. In addition to BODIPY, we envision modulation of electronegativity of chemical substituents could serve as a feasible strategy to achieve rational control of fluorescence lifetime for a variety of small molecule fluorophores.