3-stealoxy-2-(stealyloxymethyl)-1-bromopropane | 479681-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-stealoxy-2-(stealyloxymethyl)-1-bromopropane
• CAS: 479681-37-3
• 化学式: C₄₀H₈₁BrO₂
• 分子量: 673.986
• InChiKey: LZZMCIRGGWTLBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.55
• 重原子数：
  43.0
• 可旋转键数：
  39.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-stealoxy-2-(stealyloxymethyl)-1-bromopropane 、 (S)-N,N'-bis(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以34%的产率得到
  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：

  在 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 3-stealoxy-2-(stealyloxymethyl)-1-bromopropane
  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