(S)-Methoxy-phenyl-acetic acid (5S,8S)-8-((S)-2-methoxy-2-phenyl-acetoxy)-1,12-dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthren-5-yl ester | 185463-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (S)-Methoxy-phenyl-acetic acid (5S,8S)-8-((S)-2-methoxy-2-phenyl-acetoxy)-1,12-dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthren-5-yl ester
• CAS: 185463-47-2
• 化学式: C₃₈H₃₈O₆
• 分子量: 590.716
• InChiKey: FTZZQPRIFDLJRZ-WFOINRCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-Methoxy-phenyl-acetic acid (5S,8S)-8-((S)-2-methoxy-2-phenyl-acetoxy)-1,12-dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthren-5-yl ester 在 氢氧化钾 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 2.25h， 生成 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：

  (S)-(+)-alpha-甲氧基苯乙酸 在 氯化亚砜 作用下， 以 吡啶 、 苯 为溶剂， 反应 4.0h， 生成 (S)-Methoxy-phenyl-acetic acid (5S,8S)-8-((S)-2-methoxy-2-phenyl-acetoxy)-1,12-dimethyl-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthren-5-yl ester
  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