1,4-di(prop-2-ynyl)piperazine-2,5-dione | 1331827-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4-di(prop-2-ynyl)piperazine-2,5-dione
• 英文别名: 1,4-Bis(prop-2-ynyl)piperazine-2,5-dione
• CAS: 1331827-21-4
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: FEUBZLSMVNAIIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-di(prop-2-ynyl)piperazine-2,5-dione 、 11-azidoundec-1-ene 在 CuBr(PPh₃)₃ 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以40%的产率得到1,4-bis[(1-(undec-10-enyl)-1H-1,2,3-triazole-4-yl)methyl]piperazine-2,5-dione
  参考文献：
  名称：

  CH···O Hydrogen Bonds in “Clicked” Diketopiperazine-Based Amide Rotaxanes

  摘要：

  Two amide [2]rotaxanes were synthesized in high yields using a novel N,N-clipropargyl diketopiperazine axle centerpiece as the template to which the stoppers are attached through "click chemistry". H-1 and 2D NMR spectra provide evidence for two different H-bonding motifs, in one of which the triazole CH groups form C-H center dot center dot center dot O=C bonds with the wheel carbonyl O atoms. This motif can be controlled and switched reversibly by competitive anion binding.

  DOI：

  10.1021/ol201915j
• 作为产物：
  描述：

  甘氨酸酐 、 3-溴丙炔 在 sodium hydride 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 、 甲苯 为溶剂， 反应 19.0h， 以45%的产率得到1,4-di(prop-2-ynyl)piperazine-2,5-dione
  参考文献：
  名称：

  CH···O Hydrogen Bonds in “Clicked” Diketopiperazine-Based Amide Rotaxanes

  摘要：

  Two amide [2]rotaxanes were synthesized in high yields using a novel N,N-clipropargyl diketopiperazine axle centerpiece as the template to which the stoppers are attached through "click chemistry". H-1 and 2D NMR spectra provide evidence for two different H-bonding motifs, in one of which the triazole CH groups form C-H center dot center dot center dot O=C bonds with the wheel carbonyl O atoms. This motif can be controlled and switched reversibly by competitive anion binding.

  DOI：

  10.1021/ol201915j

文献信息

• Coupled Molecular Switching Processes in Ordered Mono- and Multilayers of Stimulus-Responsive Rotaxanes on Gold Surfaces
  作者：Thomas Heinrich、Christoph H.-H. Traulsen、Markus Holzweber、Sebastian Richter、Valentin Kunz、Sarah K. Kastner、Sven O. Krabbenborg、Jurriaan Huskens、Wolfgang E. S. Unger、Christoph A. Schalley

  DOI：10.1021/ja512654d

  日期：2015.4.8

  Interfaces provide the structural basis for function as, for example, encountered in nature in the membrane-embedded photosystem or in technology in solar cells. Synthetic functional multilayers of molecules cooperating in a coupled manner can be fabricated on surfaces through layer-by-layer self-assembly. Ordered arrays of stimulus-responsive rotaxanes undergoing well-controlled axle shuttling are excellent candidates for coupled mechanical motion. Such stimulus-responsive surfaces may help integrate synthetic molecular machines in larger systems exhibiting even macroscopic effects or generating mechanical work from chemical energy through cooperative action. The present work demonstrates the successful deposition of ordered mono- and multilayers of chemically switchable rotaxanes on gold surfaces. Rotaxane mono- and multilayers are shown to reversibly switch in a coupled manner between two ordered states as revealed by linear dichroism effects in angle-resolved NEXAFS spectra. Such a concerted switching process is observed only when the surfaces are well packed, while less densely packed surfaces lacking lateral order do not exhibit such effects.