(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(2-oxoethyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid | 426219-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(2-oxoethyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 426219-76-3
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: XECMIMIOWKPPPB-XNISGKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(2-oxoethyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid 在 四(三苯基膦)钯 chromium(VI) oxide 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 selenium(IV) oxide 、 硫酸 、 potassium carbonate 、 1-丙烷硫醇钠 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 33.25h， 生成 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid
  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：

  顺式璎柏酸 在 氧气 、 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以65%的产率得到(1S,4aS,5R,8aR)-1,4a-Dimethyl-6-oxo-5-(2-oxo-ethyl)-decahydro-naphthalene-1-carboxylic acid
  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

文献信息

• First Synthesis of the Antifungal Oidiolactone C from <i>trans</i>-Communic Acid:  Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds
  作者：Alejandro F. Barrero、Siméon Arseniyadis、José F. Quílez del Moral、M. Mar Herrador、M. Valdivia、D. Jiménez

  DOI：10.1021/jo0161882

  日期：2002.4.1

  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.