1,3-bis(2-naphthyl)propan-1-ol | 85180-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bis(2-naphthyl)propan-1-ol
• 英文别名: 1,3-Dinaphthalen-2-ylpropan-1-ol；1,3-dinaphthalen-2-ylpropan-1-ol
• CAS: 85180-59-2；141727-81-3；141727-82-4
• 化学式: C₂₃H₂₀O
• 分子量: 312.411
• InChiKey: XDSSDEMYYSJWRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-萘乙酮 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 1,3-bis(2-naphthyl)propan-1-ol
  参考文献：
  名称：

  Chiral recognition and molecular interaction in cellulose derivatives

  摘要：

  Nineteen 1,3-bis(aryl)propane derivatives and six model compounds with a single chromophore were used to explore the chiral discrimination ability of cellulose derivatives, in particular cellulose triphenylcarbamate (CTC), in connection with the mode of interaction of these probe molecules with adsorbents. The interaction was evaluated by conformational analysis of the probe molecules and circular dichroism. Thc 1,3-bis(aryl)propanes with 9-anthryl moieties possessed a highly limited conformation owing to thc bulky substituent and hardly changed their shape on CTC as evidenced by CD spectra; thus, they may be regarded as ''rigid'' substrates. However, these ''rigid'' substrates were resolved quite effectively. On the other hand, those with 2-naphthyl moieties possessed a number of stable conformations and could change their shape in diastereomeric complexes on CTC; thus, they may be assumed as ''soft'' substrates, against which the chiral discrimination was inefficient. The present study revealed that the optical resolution may be interpreted at least partly in terms of the ''rigid'' and ''soft'' concept.

  DOI：

  10.1021/j100193a020

文献信息

• Chiral recognition and molecular interaction in cellulose derivatives
  作者：Kenji Itoh、Tomiki Ikeda、Shigeo Tazuke、Tohru Shibata

  DOI：10.1021/j100193a020

  日期：1992.7

  Nineteen 1,3-bis(aryl)propane derivatives and six model compounds with a single chromophore were used to explore the chiral discrimination ability of cellulose derivatives, in particular cellulose triphenylcarbamate (CTC), in connection with the mode of interaction of these probe molecules with adsorbents. The interaction was evaluated by conformational analysis of the probe molecules and circular dichroism. Thc 1,3-bis(aryl)propanes with 9-anthryl moieties possessed a highly limited conformation owing to thc bulky substituent and hardly changed their shape on CTC as evidenced by CD spectra; thus, they may be regarded as ''rigid'' substrates. However, these ''rigid'' substrates were resolved quite effectively. On the other hand, those with 2-naphthyl moieties possessed a number of stable conformations and could change their shape in diastereomeric complexes on CTC; thus, they may be assumed as ''soft'' substrates, against which the chiral discrimination was inefficient. The present study revealed that the optical resolution may be interpreted at least partly in terms of the ''rigid'' and ''soft'' concept.