(1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.02,7]undecane | 858658-57-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.02,7]undecane
• 英文别名: (1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.0^2,7]undecane
• CAS: 858658-57-8
• 化学式: C₂₀H₂₈O₂S
• 分子量: 332.507
• InChiKey: UEQOXUQEOIIJPU-DGYXETDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.02,7]undecane 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 silver nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 29.0h， 生成 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
  参考文献：
  名称：

  Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries

  摘要：

  The enantioselective synthesis of either enantiomer of of alpha-alkyl-alpha-hydroxy-alpha-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee). (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.03.032
• 作为产物：
  描述：

  (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 在 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 silver nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 、 苯 为溶剂， 反应 1.5h， 生成 (1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxy-1'-phenyl-1'-propyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.02,7]undecane
  参考文献：
  名称：

  Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries

  摘要：

  The enantioselective synthesis of either enantiomer of of alpha-alkyl-alpha-hydroxy-alpha-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee). (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.03.032