5-(dimethylamino)-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzaldehyde | 828916-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(dimethylamino)-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzaldehyde
• 英文别名: 2-formyl-4-(dimethylamino)phenylboronic acid pinacol ester；5-(Dimethylamino)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde；5-(dimethylamino)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• CAS: 828916-46-7
• 化学式: C₁₅H₂₂BNO₃
• 分子量: 275.156
• InChiKey: VJNGBNDWWQMPPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(dimethylamino)-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzaldehyde 在 sodium hydroxide 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 氯化亚砜 、 cesium fluoride 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 4-(dimethylamino)-2,2'-bis-(2-ethylsulfanyl-ethyl-sulfanylmethyl)-4'-cyano-1,1'-biphenyl
  参考文献：
  名称：

  Fluorescence sensing based on cation-induced conformational switching: copper-selective modulation of the photoinduced intramolecular charge transfer of a donor–acceptor biphenyl fluorophore

  摘要：

  The fluorescence emission energy of donor-acceptor substituted biphenyls is highly sensitive towards conformational changes of the interannular twist angle. By integrating 4-dimethylamino-4'-cyano-biphenyl into the ligand backbone of a thioether-rich metal receptor we designed a fluorescence sensor that exhibits high selectivity towards copper. Upon metal binding the ligand undergoes a significant conformational change, which induces a strong hypsochromic shift of the photoinduced charge-transfer emission. Steady-state absorption and fluorescence spectroscopy revealed a high affinity towards Cu(I) with a well-defined 1:1 metal-ligand complex stoichiometry. The nature of the conformational changes upon Cu(I) coordination were analyzed in detail by H-1 NMR and 2D NOESY experiments. The spectroscopic data provide a coherent picture, which is consistent with a Boltzmann ground-state distribution of several rotamers, that are locked into a more flattened geometry upon coordination of Cu(I). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.056
• 作为产物：
  描述：

  间二甲氨基苯甲酸 在 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 1,3-二溴-5,5-二甲基海因 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 5-(dimethylamino)-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzaldehyde
  参考文献：
  名称：

  Fluorescence sensing based on cation-induced conformational switching: copper-selective modulation of the photoinduced intramolecular charge transfer of a donor–acceptor biphenyl fluorophore

  摘要：

  The fluorescence emission energy of donor-acceptor substituted biphenyls is highly sensitive towards conformational changes of the interannular twist angle. By integrating 4-dimethylamino-4'-cyano-biphenyl into the ligand backbone of a thioether-rich metal receptor we designed a fluorescence sensor that exhibits high selectivity towards copper. Upon metal binding the ligand undergoes a significant conformational change, which induces a strong hypsochromic shift of the photoinduced charge-transfer emission. Steady-state absorption and fluorescence spectroscopy revealed a high affinity towards Cu(I) with a well-defined 1:1 metal-ligand complex stoichiometry. The nature of the conformational changes upon Cu(I) coordination were analyzed in detail by H-1 NMR and 2D NOESY experiments. The spectroscopic data provide a coherent picture, which is consistent with a Boltzmann ground-state distribution of several rotamers, that are locked into a more flattened geometry upon coordination of Cu(I). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.056

文献信息

• Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant
  作者：Cedric J. Stress、Pascal J. Schmidt、Dennis. G. Gillingham

  DOI：10.1039/c6ob00168h

  日期：——

  We use kinetic data, photophysical properties, and mechanistic analyses to compare recently developed high-rate constant oxime and hydrazone formations. We show that when Schiff base formation between aldehydes and arylhydrazines is carried out with an appropriately positioned boron atom, then aromatic B–N heterocycles form irreversibly. These consist of an extended aromatic structure amenable to the

  我们使用动力学数据，光物理性质和机理分析来比较最近开发的高速率恒定肟和的形成。我们显示，当醛和芳基肼之间的席夫碱形成是通过适当定位的硼原子进行的时，则芳香族B–N杂环不可逆地形成。这些由适合特定特性（例如反应速率和荧光）的扩展的芳族结构组成。该反应在中性水性缓冲液中效果最好，并且可以设计成具有荧光性的特性，这些特性在生物缀合中特别有趣。
• Fluorescence sensing based on cation-induced conformational switching: copper-selective modulation of the photoinduced intramolecular charge transfer of a donor–acceptor biphenyl fluorophore
  作者：John Cody、Christoph J. Fahrni

  DOI：10.1016/j.tet.2004.08.056

  日期：2004.11

  The fluorescence emission energy of donor-acceptor substituted biphenyls is highly sensitive towards conformational changes of the interannular twist angle. By integrating 4-dimethylamino-4'-cyano-biphenyl into the ligand backbone of a thioether-rich metal receptor we designed a fluorescence sensor that exhibits high selectivity towards copper. Upon metal binding the ligand undergoes a significant conformational change, which induces a strong hypsochromic shift of the photoinduced charge-transfer emission. Steady-state absorption and fluorescence spectroscopy revealed a high affinity towards Cu(I) with a well-defined 1:1 metal-ligand complex stoichiometry. The nature of the conformational changes upon Cu(I) coordination were analyzed in detail by H-1 NMR and 2D NOESY experiments. The spectroscopic data provide a coherent picture, which is consistent with a Boltzmann ground-state distribution of several rotamers, that are locked into a more flattened geometry upon coordination of Cu(I). (C) 2004 Elsevier Ltd. All rights reserved.