2-[(S)-3-Phenyl-1-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.02,6]dec-4-yloxy)-propyl]-phenol | 207220-47-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-[(S)-3-Phenyl-1-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.02,6]dec-4-yloxy)-propyl]-phenol
• CAS: 207220-47-1
• 化学式: C₂₇H₃₄O₃
• 分子量: 406.565
• InChiKey: GQTKDQWHHGDCRY-WSGRUZHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[(S)-3-Phenyl-1-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.02,6]dec-4-yloxy)-propyl]-phenol 生成
  参考文献：
  名称：

  Synthesis and pharmacological activity of the stereoisomers of GP-88, a propafenone-type modulator of multidrug resistance

  摘要：

  All four stereoisomers of the propafenone-type MDR-modulator GP-88 (1) were synthesized using a combined approach with chiral pool building blocks and an acetalic protective group, which allows not only diastereoseparation but also assignment of absolute configuration via NMR spectroscopy. Those isomers with different configuration on the center of chirality in the propanolamine side chain showed statistically different PGP-inhibitory activity. Generally, the (R)-configured isomers were by a factor of nearby two higher active than the (S)-isomers. No differences in activity were observed for isomers with different configuration on the benzylic center of chirality. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00115-2
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-phenyl-1-propanol 、 (2S,2'S-(2α,2'α,3aα,3a'α,4β,4'β,7β,7'β,7aα,7a'α))-2,2'-oxybis[octahydro-7,8,8-trimethyl-4,7-methanobenzofuran] 生成 2-[(R)-3-Phenyl-1-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.02,6]dec-4-yloxy)-propyl]-phenol 、 2-[(S)-3-Phenyl-1-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.02,6]dec-4-yloxy)-propyl]-phenol
  参考文献：
  名称：

  Synthesis and pharmacological activity of the stereoisomers of GP-88, a propafenone-type modulator of multidrug resistance

  摘要：

  All four stereoisomers of the propafenone-type MDR-modulator GP-88 (1) were synthesized using a combined approach with chiral pool building blocks and an acetalic protective group, which allows not only diastereoseparation but also assignment of absolute configuration via NMR spectroscopy. Those isomers with different configuration on the center of chirality in the propanolamine side chain showed statistically different PGP-inhibitory activity. Generally, the (R)-configured isomers were by a factor of nearby two higher active than the (S)-isomers. No differences in activity were observed for isomers with different configuration on the benzylic center of chirality. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00115-2