(S)-N,N’-双对甲氧苄基-3-异丙基哌嗪-2,5-二酮 | 479681-55-5

• 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
• 中文名称: (S)-N,N’-双对甲氧苄基-3-异丙基哌嗪-2,5-二酮
• 中文别名: (S)-N,N`-双对甲氧苄基-3-异丙基哌嗪-2,5-二酮；(S)-N,N'-双对甲氧苄基-3-异丙基哌嗪-2,5-二酮
• 英文名称: 3-Isopropyl-1,4-bis-(4-methoxy-benzyl)-piperazine-2,5-dione
• 英文别名: 1,4-Bis[(4-methoxyphenyl)methyl]-3-propan-2-ylpiperazine-2,5-dione
• CAS: 479681-55-5
• 化学式: C₂₃H₂₈N₂O₄
• 分子量: 396.486
• InChiKey: KFDFRWYJTUSDJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N,N’-双对甲氧苄基-3-异丙基哌嗪-2,5-二酮 在 正丁基锂 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Homochiral Supramolecular Polymerization of an “S”-Shaped Chiral Monomer:  Translation of Optical Purity into Molecular Weight Distribution

  摘要：

  An "S"-shaped chiral motif of a p-xylylene-bridged bis(cyclic dipeptide) (1), having four hydrogen-bonding amide functionalities, formed a homochiral supramolecular polymer in solution. X-ray crystallography of a slightly modified version of 1 for an enhanced crystallinity showed one-dimensional columnar assemblies via four double hydrogen-bonding interactions. Model studies with half-protected analogues of 1 indicated a nearly perfect enantioselectivity in hydrogen-bonding dimerization. When 1 was not racemic but enriched in either of the enantiomers, a supramolecular polymer with a bimodal molecular weight distribution resulted, due to the formation of two homochiral polymers with different molecular weights. By taking advantage of this, separation of optically pure 1 from an enantiomerically unbalanced mixture was possible by means of size-exclusion chromatography.

  DOI：

  10.1021/ja028403h

文献信息

• Homochiral Supramolecular Polymerization of an “<i>S</i>”-Shaped Chiral Monomer:  Translation of Optical Purity into Molecular Weight Distribution
  作者：Yasuhiro Ishida、Takuzo Aida

  DOI：10.1021/ja028403h

  日期：2002.11.1

  An "S"-shaped chiral motif of a p-xylylene-bridged bis(cyclic dipeptide) (1), having four hydrogen-bonding amide functionalities, formed a homochiral supramolecular polymer in solution. X-ray crystallography of a slightly modified version of 1 for an enhanced crystallinity showed one-dimensional columnar assemblies via four double hydrogen-bonding interactions. Model studies with half-protected analogues of 1 indicated a nearly perfect enantioselectivity in hydrogen-bonding dimerization. When 1 was not racemic but enriched in either of the enantiomers, a supramolecular polymer with a bimodal molecular weight distribution resulted, due to the formation of two homochiral polymers with different molecular weights. By taking advantage of this, separation of optically pure 1 from an enantiomerically unbalanced mixture was possible by means of size-exclusion chromatography.