(2S,10S)-(+)-1,11-bis(triphenylmethoxy)-2,10-bis(3,5-dimethylphenyl)-3,6,9-trioxaundecane | 880498-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S,10S)-(+)-1,11-bis(triphenylmethoxy)-2,10-bis(3,5-dimethylphenyl)-3,6,9-trioxaundecane
• CAS: 880498-15-7
• 化学式: C₆₂H₆₂O₅
• 分子量: 887.171
• InChiKey: ZWDMYEDCQOTDRE-FNSAWIKJSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  871.1±60.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.77
• 重原子数：
  67.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,10S)-(+)-1,11-bis(triphenylmethoxy)-2,10-bis(3,5-dimethylphenyl)-3,6,9-trioxaundecane 在 ammonium cerium(IV) nitrate 、 硫酸 、 sodium hydride 、 对甲苯磺酸 、 乙硫醇 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.5h， 生成 (5S,13S)-21-hydroxy-5,13-bis(3,5-dimethylphenyl)-19-(2,4-dinitrophenylazo)-3,6,9,12,15-pentaoxabicyclo[15.3.1]heneicosa-1(21),17,19-triene
  参考文献：
  名称：

  Remarkable Effect of Subtle Structural Change of Chiral Pseudo-18-Crown-6 on Enantiomer-Selectivity in Complexation with Chiral Amino Alcohols

  摘要：

  Chiral receptors [(S,S)-1] and [(S,S,S,S)-2] having 1,2-dialkoxy-1-(3,5-dimethylphenyl)ethane and 1,2-dialkoxy-1-(3,5-dimethyl phenyl)cyclohexane as chiral building blocks, respectively, were prepared. Thermodynamic parameters of complexations of these and structurally related receptors [(S,S)-3] and [(S,S,S,S)-4] with 2-amino-1-propanol (5), 2-amino-2-phenylethanol (6), and 3-methylbutan-1-ol (7) in chloroform were determined. It was found that the host-guest systems that have same enantiomer-selectivity at 25 degrees C showed opposite selectivity in the enthalpy term. For example, complexations of both (SS)-1 and (SS)-3 with 5 are R-selective at 25 degrees C (Delta Delta G = 2.2 and 3.8 kJ mol(-1), respectively), whereas In terms of the enthalpy of complexation the former is S-selective (Delta Delta H = 22 kJ mol(-1)) but the latter is R-selective (Delta Delta H = 10 kJ mol(-1)).

  DOI：

  10.3987/com-05-s(k)42
• 作为产物：
  描述：

  1-(3,5-dimethylphenyl)ethane-1,2-diol 在 Lipase QL sodium hydride 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 83.0h， 生成 (2S,10S)-(+)-1,11-bis(triphenylmethoxy)-2,10-bis(3,5-dimethylphenyl)-3,6,9-trioxaundecane
  参考文献：
  名称：

  Remarkable Effect of Subtle Structural Change of Chiral Pseudo-18-Crown-6 on Enantiomer-Selectivity in Complexation with Chiral Amino Alcohols

  摘要：

  Chiral receptors [(S,S)-1] and [(S,S,S,S)-2] having 1,2-dialkoxy-1-(3,5-dimethylphenyl)ethane and 1,2-dialkoxy-1-(3,5-dimethyl phenyl)cyclohexane as chiral building blocks, respectively, were prepared. Thermodynamic parameters of complexations of these and structurally related receptors [(S,S)-3] and [(S,S,S,S)-4] with 2-amino-1-propanol (5), 2-amino-2-phenylethanol (6), and 3-methylbutan-1-ol (7) in chloroform were determined. It was found that the host-guest systems that have same enantiomer-selectivity at 25 degrees C showed opposite selectivity in the enthalpy term. For example, complexations of both (SS)-1 and (SS)-3 with 5 are R-selective at 25 degrees C (Delta Delta G = 2.2 and 3.8 kJ mol(-1), respectively), whereas In terms of the enthalpy of complexation the former is S-selective (Delta Delta H = 22 kJ mol(-1)) but the latter is R-selective (Delta Delta H = 10 kJ mol(-1)).

  DOI：

  10.3987/com-05-s(k)42