(1S,2R,3S,9R,12S,16R)-1,12-dimethyl-3-phenylselanyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadec-7-ene-4,11-dione | 426219-82-1

• 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: (1S,2R,3S,9R,12S,16R)-1,12-dimethyl-3-phenylselanyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadec-7-ene-4,11-dione
• CAS: 426219-82-1
• 化学式: C₂₂H₂₄O₄Se
• 分子量: 431.39
• InChiKey: SXGBWHVIWIOLPJ-GAQXIGJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (1S,2R,3S,9R,12S,16R)-1,12-dimethyl-3-phenylselanyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadec-7-ene-4,11-dione 在 吡啶 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.08h， 以345 mg的产率得到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 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 碘 、 silver nitrate 、 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 32.66h， 生成 (1S,2R,3S,9R,12S,16R)-1,12-dimethyl-3-phenylselanyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadec-7-ene-4,11-dione
  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.