N-(di-3,5-tert-butylbenzyl)-δ-valerolactam | 360569-39-7

• 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: N-(di-3,5-tert-butylbenzyl)-δ-valerolactam
• 英文别名: 1-[(3,5-Ditert-butylphenyl)methyl]piperidin-2-one
• CAS: 360569-39-7
• 化学式: C₂₀H₃₁NO
• 分子量: 301.472
• InChiKey: ADEYDXDTSNYBDG-UHFFFAOYSA-N

物化性质

• 沸点：
  403.1±24.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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-(di-3,5-tert-butylbenzyl)-δ-valerolactam 在 盐酸 、 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.33h， 生成 2-{5-[tert-butoxycarbonyl(3,5-di-tert-butylbenzyl)amino]pentanoylamino}-3-phenylpropanoic acid methyl ester
  参考文献：
  名称：

  Structure−Function Relationship of Amino Acid−[2]Rotaxanes

  摘要：

  Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as the ring. A relative measure of the intramolecular interaction energies between the functional groups in DMSO/water mixtures is obtained by comparing their pK(a) values. Rotaxane structures were investigated through 2D NMR analysis and molecular dynamics simulations. Association constants for complexes of amino acids and rotaxanes in various protonation states were determined in a variety of solvent systems by H-1 NMR analysis. The unique intracomponent interactions that exist in the rotaxanes and their ability to act as artificial receptors are discussed.

  DOI：

  10.1021/jo026530q
• 作为产物：
  描述：

  哌啶酮 、 3,5-二叔丁基苄溴 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以76%的产率得到N-(di-3,5-tert-butylbenzyl)-δ-valerolactam
  参考文献：
  名称：

  Structure−Function Relationship of Amino Acid−[2]Rotaxanes

  摘要：

  Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as the ring. A relative measure of the intramolecular interaction energies between the functional groups in DMSO/water mixtures is obtained by comparing their pK(a) values. Rotaxane structures were investigated through 2D NMR analysis and molecular dynamics simulations. Association constants for complexes of amino acids and rotaxanes in various protonation states were determined in a variety of solvent systems by H-1 NMR analysis. The unique intracomponent interactions that exist in the rotaxanes and their ability to act as artificial receptors are discussed.

  DOI：

  10.1021/jo026530q

文献信息

• Facile Synthesis of Rotaxanes through Condensation Reactions of DCC-[2]Rotaxanes
  作者：Donald W. Zehnder、David B. Smithrud

  DOI：10.1021/ol016107o

  日期：2001.8.9

  [GRAPHICS]In this Letter, we present an easy method for the synthesis of rotaxanes using a novel DCC-[2]rotaxane. The DCC-[2]rotaxane is composed of dibenzo-24-crown-8 ether, an amino acid tether, and di-tert-butyl phenyl rings as blocking groups. It is relatively stable and can be purified by column chromatography. A series of model rotaxanes were obtained in good yields by condensing the DCC-[2]rotaxanes with N-(2-aminoethyl)-3,5-di-tert-butylbenzylamide in acetonitrile and chloroform.