(4aS,6aR,14aR,14bS)-4,4,6a,14b-tetramethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydropicene | 1388152-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (4aS,6aR,14aR,14bS)-4,4,6a,14b-tetramethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydropicene
• 英文别名: (4aS,6aR,14aR,14bS)-4,4,6a,14b-tetramethyl-2,3,4a,5,6,13,14,14a-octahydro-1H-picene
• CAS: 1388152-63-3
• 化学式: C₂₆H₃₄
• 分子量: 346.556
• InChiKey: RYJFJEONHIHTAZ-LCGRTSHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)naphthalene 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， 反应 6.0h， 生成 (4aS,6aR,14aR,14bS)-4,4,6a,14b-tetramethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydropicene 、 (4aR,6aS,14aS,14bR)-4,4,6a,14b-tetramethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydropicene
  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.