(5S,13S)-19-Methoxy-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol | 209622-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5S,13S)-19-Methoxy-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol
• CAS: 209622-59-3
• 化学式: C₂₉H₃₄O₇
• 分子量: 494.585
• InChiKey: KJTNXYZMDPLHSB-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (5S,13S)-19-Methoxy-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol 在 ammonium cerium(IV) nitrate 、 硫酸 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 2.0h， 生成 (5S,13S)-19-(2,4-Dinitro-phenylazo)-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol
  参考文献：
  名称：

  Preparation and temperature-dependent enantioselectivities of homochiral phenolic crown ethers having aryl chiral barriers: thermodynamic parameters for enantioselective complexation with chiral amines

  摘要：

  Homochiral crown ether (S,S)-1 containing I-naphthyl groups as chiral barriers together with the phenol moiety was prepared by using (S)-3 as a chiral subunit which was resolved in enantiomerically pure form by lipase-catalyzed enantioselective acylation of (+/-)-3. Homochiral phenolic crown ether (S,S)-2, containing phenyl groups as chiral barriers, was also prepared from (S)-5 which was derived from (S)-mandelic acid. The association constants for their complexes with chiral amines in CHCl(3) were determined at various temperatures by the UV-visible spectroscopic method demonstrating that the crown ethers (S,S)-1 and (S,S)-2 displayed the large Delta(R-S)Delta G values of 6.2 and 6.4 kJ mol(-1), respectively, towards the amine 21 at 15 degrees C. Thermodynamic parameters for complex formation were also determined and a linear correlation between T Delta(R-S)Delta S and Delta(R-S)Delta H values was observed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00638-1
• 作为产物：
  描述：

  (5S,13S)-19,21-dimethoxy-5,13-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-triene 在 sodium hydride 、 乙硫醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以77%的产率得到(5S,13S)-19-Methoxy-5,13-diphenyl-3,6,9,12,15-pentaoxa-bicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol
  参考文献：
  名称：

  Preparation and temperature-dependent enantioselectivities of homochiral phenolic crown ethers having aryl chiral barriers: thermodynamic parameters for enantioselective complexation with chiral amines

  摘要：

  Homochiral crown ether (S,S)-1 containing I-naphthyl groups as chiral barriers together with the phenol moiety was prepared by using (S)-3 as a chiral subunit which was resolved in enantiomerically pure form by lipase-catalyzed enantioselective acylation of (+/-)-3. Homochiral phenolic crown ether (S,S)-2, containing phenyl groups as chiral barriers, was also prepared from (S)-5 which was derived from (S)-mandelic acid. The association constants for their complexes with chiral amines in CHCl(3) were determined at various temperatures by the UV-visible spectroscopic method demonstrating that the crown ethers (S,S)-1 and (S,S)-2 displayed the large Delta(R-S)Delta G values of 6.2 and 6.4 kJ mol(-1), respectively, towards the amine 21 at 15 degrees C. Thermodynamic parameters for complex formation were also determined and a linear correlation between T Delta(R-S)Delta S and Delta(R-S)Delta H values was observed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00638-1