N,N-diethylpyrene-1-carboxamide | 1262295-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N,N-diethylpyrene-1-carboxamide
• CAS: 1262295-78-2
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: IYHJWUUJKMKNHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethylpyrene-1-carboxamide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以78%的产率得到N,N-diethylpyrene-1-carbothioamide
  参考文献：
  名称：

  Fluorescent Signaling of Oxone by Desulfurization of Thioamide

  摘要：

  The chemosignaling of the oxidant Oxone by selective desulfurization of a thioamide was Investigated. Pyrene-thioamide was efficiently converted to its amide analogue by reaction with Oxone, resulting in a pronounced fluorescent turn-on type signaling. Selective signaling of Ozone in aqueous solution was possible in the presence of representative alkali and alkaline earth metal ions, as well as common anions.

  DOI：

  10.1021/ol102550c
• 作为产物：
  描述：

  1-芘甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 生成 N,N-diethylpyrene-1-carboxamide
  参考文献：
  名称：

  具有羰基基团的多环芳烃发光过程的其他见解：萘，蒽和P的仲N-烷基和叔N，N-二烷基羧酰胺的光物理性质

  摘要：

  在这里，我们报道了N-烷基和N，N-二烷基羧酰胺基团对多环芳烃发色团的荧光性质的取代作用，从而控制了它们的荧光性质。使用具有不同极性的溶剂获得的化合物的荧光性质几乎没有变化，表明改性的化合物没有形成电荷转移态。在低温（78 K）和粘性溶剂中进行的TD-DFT计算和测量表明，N-烷基和N，N-二烷基羧酰胺基团倾向于减少来自系统间交叉的贡献并增加来自内部转化的贡献。考虑到醛和酮等低荧光羰基化合物的荧光机理是通过体系间交叉控制的，而羧酸和酯等高发光羰基化合物的荧光机理是通过辐射过程控制的，可以说是光物理过程。的ñ -烷基和ñ，ñ二烷基甲酰胺是新颖的。另外，对于激发态的计算结果表明，除了溶剂粘度和温度以外，还可以通过选择合适的多环芳族烃或酰胺结构来控制这种作用。

  DOI：

  10.1021/jo300317r

文献信息

• [EN] COMPOUND FOR USE IN PEPTIDE SYNTHESIS<br/>[FR] COMPOSÉ POUR L'UTILISATION DANS LA SYNTHÈSE DE PEPTIDES
  申请人：UNIV NANYANG TECH

  公开号：WO2012005691A1

  公开（公告）日：2012-01-12

  The present invention generally relates to processes and methods of peptide and protein synthesis. The present invention also relates to specific compounds for use in such processes and methods. It is shown herein that peptides with a C-terminal tertiary N,N-bis(2-mercaptoethyl)-amide (BMEA) undergo N-to-S acyl transfer at weakly acidic pH to form a transient thioester which can be captured for direct ligation with a cysteinyl peptide. These C-terminal BMEA peptides are easily prepared with standard Fmoc solid-phase synthesis protocols, thus giving a very convenient access to the thioester components for native chemical ligation.

  本发明一般涉及肽和蛋白质合成的过程和方法。本发明还涉及用于这些过程和方法的特定化合物。本文显示，带有C-末端三级N,N-双(2-巯乙基)-酰胺(BMEA)的肽在弱酸性pH下发生N-到-S酰基转移，形成一种暂时的硫酯，可用于直接与半胱氨酸肽进行连接。这些C-末端BMEA肽可使用标准Fmoc固相合成协议轻松制备，从而非常方便地获得用于原生化学连接的硫酯组分。
• Synthesis, luminescence properties, and theoretical insights of N-alkyl- or N,N-dialkyl-pyrene-1-carboxamide
  作者：Yosuke Niko、Susumu Kawauchi、Gen-ichi Konishi

  DOI：10.1016/j.tetlet.2011.07.020

  日期：2011.9

  We report the synthesis and photophysical properties of N-alkyl- or N,N-dialkyl-pyrene-1-carboxamide. These derivatives, as well as pyrene, exhibited blue emission. N-Alkyl-type derivatives exhibited strong fluorescence emission (Phi(fl) = 0.61 in EtOH) in both nonpolar and polar solvents. On the other hand. N,N-dialkyl-type derivatives showed weak fluorescence emission (Phi(fl) <0.01) due to vibrational deactivation. However, in highly viscous solvents such as glycerin, the quantum efficiencies of N-alkyl-type (Phi(fl) = 0.91) and N,N-dialkyl-type (Phi(fl) = 0.082) derivatives were increased. We also investigated the fluorescence mechanism of these compounds using time-dependent density-functional theory (TD-DFT). From these results, we find that highly fluorescent pyrene-1-carboxamide derivatives can be designed by introducing an appropriate functional group at the nitrogen atom of the amide. Thus, N,N-dialkyl-type pyrene-1-carboxamide has considerable potential for use in applications such as environmental response sensors and probes. (C) 2011 Elsevier Ltd. All rights reserved.
• Peptidyl <i>N</i>,<i>N</i>-Bis(2-mercaptoethyl)-amides as Thioester Precursors for Native Chemical Ligation
  作者：Wen Hou、Xiaohong Zhang、Fupeng Li、Chuan-Fa Liu

  DOI：10.1021/ol102735k

  日期：2011.2.4

  With two beta-mercaptoethyl groups on the N, a tertiary amide of structure 1 is always poised for intramolecular thioesterification however it flips about the C-N bond. It is shown that a peptide with such a C-terminal N,N-bis(2-mercaptoethyl)-amide (BMEA) can be used directly for native chemical ligation (NCL). These BMEA peptides are easily prepared with standard Fmoc-solid phase peptide synthesis protocols, thus giving a very convenient access to the thioester components for NCL.
• Additional Insights into Luminescence Process of Polycyclic Aromatic Hydrocarbons with Carbonyl Groups: Photophysical Properties of Secondary <i>N</i>-Alkyl and Tertiary <i>N</i>,<i>N</i>-Dialkyl Carboxamides of Naphthalene, Anthracene, and Pyrene
  作者：Yosuke Niko、Yuki Hiroshige、Susumu Kawauchi、Gen-ichi Konishi

  DOI：10.1021/jo300317r

  日期：2012.4.20

  substitution effects of N-alkyl and N,N-dialkyl carboxamide groups on the fluorescence properties of polycyclic aromatic hydrocarbon chromophores, so as to control their fluorescence properties. The fluorescence properties of compounds obtained using solvents with different polarities showed very little change, indicating that the modified compounds do not form charge transfer states. TD-DFT calculations and

  在这里，我们报道了N-烷基和N，N-二烷基羧酰胺基团对多环芳烃发色团的荧光性质的取代作用，从而控制了它们的荧光性质。使用具有不同极性的溶剂获得的化合物的荧光性质几乎没有变化，表明改性的化合物没有形成电荷转移态。在低温（78 K）和粘性溶剂中进行的TD-DFT计算和测量表明，N-烷基和N，N-二烷基羧酰胺基团倾向于减少来自系统间交叉的贡献并增加来自内部转化的贡献。考虑到醛和酮等低荧光羰基化合物的荧光机理是通过体系间交叉控制的，而羧酸和酯等高发光羰基化合物的荧光机理是通过辐射过程控制的，可以说是光物理过程。的ñ -烷基和ñ，ñ二烷基甲酰胺是新颖的。另外，对于激发态的计算结果表明，除了溶剂粘度和温度以外，还可以通过选择合适的多环芳族烃或酰胺结构来控制这种作用。
• Fluorescent Signaling of Oxone by Desulfurization of Thioamide
  作者：Suyoung Eor、Jiyoung Hwang、Myung Gil Choi、Suk-Kyu Chang

  DOI：10.1021/ol102550c

  日期：2011.2.4

  The chemosignaling of the oxidant Oxone by selective desulfurization of a thioamide was Investigated. Pyrene-thioamide was efficiently converted to its amide analogue by reaction with Oxone, resulting in a pronounced fluorescent turn-on type signaling. Selective signaling of Ozone in aqueous solution was possible in the presence of representative alkali and alkaline earth metal ions, as well as common anions.