(1S,4aS,5S,8aR)-5-((E)-2-Methoxy-2-trimethylsilanyloxy-vinyl)-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid methyl ester | 426219-79-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,4aS,5S,8aR)-5-((E)-2-Methoxy-2-trimethylsilanyloxy-vinyl)-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid methyl ester
• CAS: 426219-79-6
• 化学式: C₂₁H₃₆O₄Si
• 分子量: 380.6
• InChiKey: INPJWWBCXTWYPA-YZQWZULRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯基氯化硒 、 (1S,4aS,5S,8aR)-5-((E)-2-Methoxy-2-trimethylsilanyloxy-vinyl)-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid methyl ester 以 四氢呋喃 为溶剂， 生成 (1S,4aS,5S,8aR)-5-((S)-Methoxycarbonyl-phenylselanyl-methyl)-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  First Synthesis of the Antifungal Oidiolactone C from trans-Communic Acid:  Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds

  摘要：

  The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(H), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.

  DOI：

  10.1021/jo0161882
• 作为产物：
  描述：

  acrostalic acid 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 (1S,4aS,5S,8aR)-5-((E)-2-Methoxy-2-trimethylsilanyloxy-vinyl)-1,4a-dimethyl-6-methylene-decahydro-naphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  First Synthesis of the Antifungal Oidiolactone C from trans-Communic Acid:  Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds

  摘要：

  The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(H), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.

  DOI：

  10.1021/jo0161882