4-[5-(6-methoxynaphthalen-2-yl)-1H-[1,2,3]triazol-4-yl]benzaldehyde | 1114962-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[5-(6-methoxynaphthalen-2-yl)-1H-[1,2,3]triazol-4-yl]benzaldehyde
• 英文别名: 4-[5-(6-methoxynaphthalen-2-yl)-2H-triazol-4-yl]benzaldehyde
• CAS: 1114962-69-4
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: ZZNFQVMRFAXIIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[5-(6-methoxynaphthalen-2-yl)-1H-[1,2,3]triazol-4-yl]benzaldehyde 在 [pentamethylcyclopentadienyl*Ir(N-phenyl-2-pyridinecarboxamidate)Cl] 、 sodium formate 、 还原型辅酶Ⅰ 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以13%的产率得到
  参考文献：
  名称：

  Intracellular Transfer Hydrogenation Mediated by Unprotected Organoiridium Catalysts

  摘要：

  In the present work, we show for the first time that the conversion of aldehydes to alcohols can be achieved using "unprotected" iridium transfer hydrogenation catalysts inside living cells. The reactions were observed in real time by confocal fluorescence microscopy using a Bodipy fluorogenic substrate. We propose that the reduced cofactor nicotinamide adenine dinucleotide (NADH) is a possible hydride source inside the cell based on studies using pyruvate as a cellular redox modulator. We expect that this biocompatible reductive chemistry will be broadly useful to practitioners working at the interface of chemistry and the life sciences.

  DOI：

  10.1021/jacs.7b03872
• 作为产物：
  描述：

  4-(6-methoxynaphthalen-2-ylethynyl)benzaldehyde 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以67%的产率得到4-[5-(6-methoxynaphthalen-2-yl)-1H-[1,2,3]triazol-4-yl]benzaldehyde
  参考文献：
  名称：

  A Fluorogenic Aldehyde Bearing a 1,2,3-Triazole Moiety for Monitoring the Progress of Aldol Reactions

  摘要：

  We have developed a new type of fluorogenic aldehyde bearing a 1,2,3-triazole moiety that is useful for monitoring the progress of aldol reactions through an increase in fluorescence. Whereas 6-methoxy-2-naphthaldehyde was highly fluorescent, the fluorogenic aldehyde, 4-formylbenzene connected to the 6-methoxy-2-naphthyl group through a 1,2,3-triazole moiety, was essentially nonfluorescent in aqueous solutions. We suggest that the 4-formylphenyl group acts as a quencher to suppress the fluorescence of the 6-methoxy-2-naphthyltriazole moiety. The product of the aldol reaction of this aldehyde does not have a quenching moiety and showed more than 800-fold higher fluorescence than the aldehyde. Assay systems using the fluorogenic aldehyde were validated by screening of aldol catalysts, ranking of the activities of the catalysts, and evaluation of reaction conditions.

  DOI：

  10.1021/jo900013w

文献信息

• A Fluorogenic Aldehyde Bearing a 1,2,3-Triazole Moiety for Monitoring the Progress of Aldol Reactions
  作者：Hai-Ming Guo、Fujie Tanaka

  DOI：10.1021/jo900013w

  日期：2009.3.20

  We have developed a new type of fluorogenic aldehyde bearing a 1,2,3-triazole moiety that is useful for monitoring the progress of aldol reactions through an increase in fluorescence. Whereas 6-methoxy-2-naphthaldehyde was highly fluorescent, the fluorogenic aldehyde, 4-formylbenzene connected to the 6-methoxy-2-naphthyl group through a 1,2,3-triazole moiety, was essentially nonfluorescent in aqueous solutions. We suggest that the 4-formylphenyl group acts as a quencher to suppress the fluorescence of the 6-methoxy-2-naphthyltriazole moiety. The product of the aldol reaction of this aldehyde does not have a quenching moiety and showed more than 800-fold higher fluorescence than the aldehyde. Assay systems using the fluorogenic aldehyde were validated by screening of aldol catalysts, ranking of the activities of the catalysts, and evaluation of reaction conditions.
• Intracellular Transfer Hydrogenation Mediated by Unprotected Organoiridium Catalysts
  作者：Sohini Bose、Anh H. Ngo、Loi H. Do

  DOI：10.1021/jacs.7b03872

  日期：2017.7.5

  In the present work, we show for the first time that the conversion of aldehydes to alcohols can be achieved using "unprotected" iridium transfer hydrogenation catalysts inside living cells. The reactions were observed in real time by confocal fluorescence microscopy using a Bodipy fluorogenic substrate. We propose that the reduced cofactor nicotinamide adenine dinucleotide (NADH) is a possible hydride source inside the cell based on studies using pyruvate as a cellular redox modulator. We expect that this biocompatible reductive chemistry will be broadly useful to practitioners working at the interface of chemistry and the life sciences.