(4S,9S,17S,22S)-(+)-27,29-dimethoxy-9,17-bis(3,5-dimethylphenyl)-3,10,13,16,23-pentaoxatetracyclo[23.3.1.0^4,9.0^17,22]nonacosa-1(29),25,27-triene | 327039-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S,9S,17S,22S)-(+)-27,29-dimethoxy-9,17-bis(3,5-dimethylphenyl)-3,10,13,16,23-pentaoxatetracyclo[23.3.1.0^4,9.0^17,22]nonacosa-1(29),25,27-triene
• 英文别名: (4S,9S,17S,22S)-9,17-bis(3,5-dimethylphenyl)-27,29-dimethoxy-3,10,13,16,23-pentaoxatetracyclo[23.3.1.04,9.017,22]nonacosa-1(28),25(29),26-triene
• CAS: 327039-79-2
• 化学式: C₄₂H₅₆O₇
• 分子量: 672.902
• InChiKey: WBJDKURQXRAAMA-ZSMOYPKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  49
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,9S,17S,22S)-(+)-27,29-dimethoxy-9,17-bis(3,5-dimethylphenyl)-3,10,13,16,23-pentaoxatetracyclo[23.3.1.0^4,9.0^17,22]nonacosa-1(29),25,27-triene 在 C(NH₄)2(NO₃)6 、 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.5h， 生成 (4S,9S,17S,22S)-(+)-9,17-bis(3,5-dimethylphenyl)-3,10,13,16,23-pentaoxatetracyclo[23.3.1.0^4,9.0^17,22]nonacosa-25,28-diene-27,29-dione
  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：

  5,5'-((1S,1'S,2S,2'S)-((oxybis(ethane-2,1-diyl))bis(oxy))bis(2-(methoxymethoxy)cyclohexane-1,1-diyl))bis(1,3-dimethylbenzene) 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 40.0h， 生成 (4S,9S,17S,22S)-(+)-27,29-dimethoxy-9,17-bis(3,5-dimethylphenyl)-3,10,13,16,23-pentaoxatetracyclo[23.3.1.0^4,9.0^17,22]nonacosa-1(29),25,27-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

文献信息

• Remarkable Effect of Subtle Structural Change of Chiral Pseudo-18-Crown-6 on Enantiomer-Selectivity in Complexation with Chiral Amino Alcohols
  作者：Keiji Hirose、Yoshito Tobe、Pakatip Aksharanandana、Michiko Suzuki、Kiyoshi Wada、Koichiro Naemura

  DOI：10.3987/com-05-s(k)42

  日期：——

  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)).