(5S,8S)-1,12-Dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthrene-5,8-diol | 185463-49-4

• 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: (5S,8S)-1,12-Dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthrene-5,8-diol
• CAS: 185463-49-4
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: VLVZYXMOGGZGPI-FDRFZEDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (5S,8S)-1,12-Dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthrene-5,8-diol 以 吡啶 为溶剂， 反应 1.25h， 以75%的产率得到5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-diyl diacetate
  参考文献：
  名称：

  Synthesis of a Chiral Helical Molecular Template Based on trans-5,6,6a,7,8,12b-Hexahydro-1,12-dimethylbenzo[c]phenanthrene- 5,8-dione

  摘要：

  Reduction of trans-5,5,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-dione (1, R(1)=R(4)=H, R(2)=R(3)=CH3) with lithium aluminum hydride yielded stereoselectively (5RS,8RS)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene 2, X=H. These diols proved to be configurationally stable chiral molecular templates capable of straightforward modification by attachment of molecular elements of different length and kind. The structures of the diacetate 2, X=COCH3, and (5R,8R)-(-)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo- [c]phenanthrene-5,8-diyl di-p-bromobenzoate (2a, X=p-BrC6H4CO), as well as the absolute configuration of the latter were obtained by X-ray crystallography.

  DOI：

  10.1021/jo961254z
• 作为产物：
  描述：

  (5R,8R)-1,12-Dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthrene-5,8-diol 在 氢氧化钾 作用下， 以 吡啶 、 乙醇 、 苯 为溶剂， 反应 2.0h， 生成 (5S,8S)-1,12-Dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthrene-5,8-diol
  参考文献：
  名称：

  Synthesis of a Chiral Helical Molecular Template Based on trans-5,6,6a,7,8,12b-Hexahydro-1,12-dimethylbenzo[c]phenanthrene- 5,8-dione

  摘要：

  Reduction of trans-5,5,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-dione (1, R(1)=R(4)=H, R(2)=R(3)=CH3) with lithium aluminum hydride yielded stereoselectively (5RS,8RS)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene 2, X=H. These diols proved to be configurationally stable chiral molecular templates capable of straightforward modification by attachment of molecular elements of different length and kind. The structures of the diacetate 2, X=COCH3, and (5R,8R)-(-)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo- [c]phenanthrene-5,8-diyl di-p-bromobenzoate (2a, X=p-BrC6H4CO), as well as the absolute configuration of the latter were obtained by X-ray crystallography.

  DOI：

  10.1021/jo961254z