dimethyl 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioate | 291748-33-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioate
• 英文别名: Methyl 2-[(1S,5S,8aR)-5-(methoxycarbonyl)-5,8a-dimethyl-2-methylene-1,5,6,7,8,4a,8a-heptahydronaphthyl]acetate；methyl (1S,4aR,5S,8aR)-5-(2-methoxy-2-oxoethyl)-1,4a-dimethyl-6-methylidene-3,4,5,8a-tetrahydro-2H-naphthalene-1-carboxylate
• CAS: 291748-33-9
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: AJUGDJQAYHMVHJ-JFTQMJAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  dimethyl 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioate 在 1-丙烷硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid
  参考文献：
  名称：

  Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction. Synthesis of oidiolactone C

  摘要：

  A new route towards podolactone skeleton compounds, including the recently discovered Oidiolactone C, is described, using Pd-catalysed elimination of allylic trifluoroacetates and Pd-catalysed bislactonisation as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00815-7
• 作为产物：
  描述：

  dimethyl 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate 在 四(三苯基膦)钯 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 selenium(IV) oxide 、 potassium carbonate 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.25h， 生成 dimethyl 13,14,15,16-tetranorlabda-6,8(17)-diene-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

• Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction. Synthesis of oidiolactone C
  作者：Alejandro F Barrero、José F Quı́lez Del Moral、Juan M Cuerva、E Cabrera、David Jiménez-González

  DOI：10.1016/s0040-4039(00)00815-7

  日期：2000.7

  A new route towards podolactone skeleton compounds, including the recently discovered Oidiolactone C, is described, using Pd-catalysed elimination of allylic trifluoroacetates and Pd-catalysed bislactonisation as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.