(3S,3'S,6R,6'R)-6,6'-(1,4-phenylenebis(methylene))bis(1-benzyl-3-isopropyl-4-(4-methoxybenzyl)piperazine-2,5-dione) | 479681-31-7

• 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: (3S,3'S,6R,6'R)-6,6'-(1,4-phenylenebis(methylene))bis(1-benzyl-3-isopropyl-4-(4-methoxybenzyl)piperazine-2,5-dione)
• CAS: 479681-31-7
• 化学式: C₅₂H₅₈N₄O₆
• 分子量: 835.056
• InChiKey: WMAKKSVCXMCXTL-UYVQAEDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  62.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.7
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,3'S,6R,6'R)-6,6'-(1,4-phenylenebis(methylene))bis(1-benzyl-3-isopropyl-4-(4-methoxybenzyl)piperazine-2,5-dione) 在 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 8.0h， 以21%的产率得到(3S,6R)-1-benzyl-6-[[4-[[(2R,5S)-1-benzyl-3,6-dioxo-5-propan-2-ylpiperazin-2-yl]methyl]phenyl]methyl]-3-propan-2-ylpiperazine-2,5-dione
  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
• 作为产物：
  描述：

  (2S)-1-苄基-2-异丙基哌嗪 在 正丁基锂 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,3'S,6R,6'R)-6,6'-(1,4-phenylenebis(methylene))bis(1-benzyl-3-isopropyl-4-(4-methoxybenzyl)piperazine-2,5-dione)
  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