(4aS,10aS)-5,7-dimethoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene | 1388152-55-3

• 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: (4aS,10aS)-5,7-dimethoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene
• 英文别名: (4aS,10aS)-5,7-dimethoxy-1,1,4a-trimethyl-2,3,4,9,10,10a-hexahydrophenanthrene
• CAS: 1388152-55-3
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: VOVSFDQLXVLVMQ-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-1-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dimethoxybenzene 在 (R)-3,3'-dichloro-1,1'-binaphthalene-2,2'-diol 、 氯化锑(V) 作用下， 以 二氯甲烷 为溶剂， 生成 (4aR,10aR)-5,7-dimethoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 、 (4aS,10aS)-5,7-dimethoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene
  参考文献：
  名称：

  Highly Enantioselective Proton-Initiated Polycyclization of Polyenes

  摘要：

  This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantio-selective proton-initiated polycyclization promoted by the 11 complex of o,o'-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.

  DOI：

  10.1021/ja305851h

文献信息

• Highly Enantioselective Proton-Initiated Polycyclization of Polyenes
  作者：Karavadhi Surendra、E. J. Corey

  DOI：10.1021/ja305851h

  日期：2012.7.25

  This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantio-selective proton-initiated polycyclization promoted by the 11 complex of o,o'-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.