(1R,4aS,10aR)-7-Isopropyl-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester | 217952-89-1

• 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: (1R,4aS,10aR)-7-Isopropyl-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
• 英文别名: methyl (1R,4aS,10aR)-6-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 217952-89-1
• 化学式: C₃₁H₃₈O₄
• 分子量: 474.64
• InChiKey: IMLIKBQFXNCCHK-SITINQCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4aS,10aR)-7-Isopropyl-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 在 一水合肼 作用下， 以 氘代甲醇 为溶剂， 生成 (1R,4aS,10aR)-7-Isopropyl-6-[5-(4-methoxy-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  New Methyl Dehydroabietate Derivatives: Synthesis and Structural Characterization

  摘要：

  The synthesis of some new chalcone and pyrazole type derivatives of methyl dehydroabietate is described. All compounds were exhaustively characterized using NMR and MS techniques. In order to confirm the information obtained by those techniques, the X-ray single crystal structures of methyl 12-acetyldehydroabietate and methyl 12-(4-methoxycinnamoyl)-dehydroabietate were determined. Molecular mechanics calculations were performed in order to evaluate the steric influence of the bulk of the C-12 substituent on the conformational preference of the isopropyl group in these derivatives. The energy barriers of 52-3 and 53.6 kJ/mol found for the two compounds indicated that the C-12 substituent hinders the free rotation of the isopropyl group in both cases.

  DOI：

  10.1007/pl00010130
• 作为产物：
  描述：

  methyl 12-acetyl-dehydroabietate 、 4-甲氧基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以80%的产率得到(1R,4aS,10aR)-7-Isopropyl-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  New Methyl Dehydroabietate Derivatives: Synthesis and Structural Characterization

  摘要：

  The synthesis of some new chalcone and pyrazole type derivatives of methyl dehydroabietate is described. All compounds were exhaustively characterized using NMR and MS techniques. In order to confirm the information obtained by those techniques, the X-ray single crystal structures of methyl 12-acetyldehydroabietate and methyl 12-(4-methoxycinnamoyl)-dehydroabietate were determined. Molecular mechanics calculations were performed in order to evaluate the steric influence of the bulk of the C-12 substituent on the conformational preference of the isopropyl group in these derivatives. The energy barriers of 52-3 and 53.6 kJ/mol found for the two compounds indicated that the C-12 substituent hinders the free rotation of the isopropyl group in both cases.

  DOI：

  10.1007/pl00010130