(1R,2R,9R,12S,16R)-1,12-dimethyl-4-trimethylsilyloxy-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-3,7-dien-11-one | 426219-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (1R,2R,9R,12S,16R)-1,12-dimethyl-4-trimethylsilyloxy-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-3,7-dien-11-one
• CAS: 426219-81-0
• 化学式: C₁₉H₂₈O₄Si
• 分子量: 348.514
• InChiKey: UHPDZNXMKYQNDP-KAKNBIBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,9R,12S,16R)-1,12-dimethyl-4-trimethylsilyloxy-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-3,7-dien-11-one 在 吡啶 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.08h， 生成 CJ-14445
  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：

  13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid 在 palladium diacetate 、 对苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 168.66h， 生成 (1R,2R,9R,12S,16R)-1,12-dimethyl-4-trimethylsilyloxy-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-3,7-dien-11-one
  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.