dimethyl 8-oxo-13,14,15,16,17-pentanorlabd-6-ene-12,19-dioate | 426219-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 8-oxo-13,14,15,16,17-pentanorlabd-6-ene-12,19-dioate
• 英文别名: Methyl 2-[(5S,8aS,1R)-5-(methoxycarbonyl)-5,8a-dimethyl-2-oxo-1,5,6,7,8,4a,8a-heptahydronaphthyl]acetate；methyl (1S,4aS,5R,8aR)-5-(2-methoxy-2-oxoethyl)-1,4a-dimethyl-6-oxo-3,4,5,8a-tetrahydro-2H-naphthalene-1-carboxylate
• CAS: 426219-75-2
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: MCDOLXWSXGKCKB-AADNMHCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 8-oxo-13,14,15,16,17-pentanorlabd-6-ene-12,19-dioate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 (1S,4aS,5R,6S,8aR)-6-Hydroxy-5-(2-hydroxy-ethyl)-1,4a,6-trimethyl-1,2,3,4,4a,5,6,8a-octahydro-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：

  8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioic acid 在 苯基氯化硒 作用下， 以 乙酸乙酯 为溶剂， 反应 60.25h， 生成 dimethyl 8-oxo-13,14,15,16,17-pentanorlabd-6-ene-12,19-dioate
  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.