dimethyl 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate | 39668-50-3

• 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-tetranorlabd-8(17)-ene-12,19-dioate
• 英文别名: methyl (1S,4aR,5S,8aR)-5-(2-methoxy-2-oxo-ethyl)-1,4a-dimethyl-6-methylene-decalin-1-carboxylate；methyl (1S,4aR,5S,8aR)-5-(2-methoxy-2-oxoethyl)-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 39668-50-3
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: PEEWTCSWPSHLQM-JFTQMJAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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-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 、 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：

  Methyl (12R/S,13R/S)-12,13-epoxylabda-8⁽¹⁷⁾,14-dien-19-oate 在 chromium(VI) oxide 、 硫酸 、 过碘酸 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 1.0h， 生成 dimethyl 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate
  参考文献：
  名称：

  Enantiospecific syntheses of the potent bioactives nagilactone F and the mould metabolite LL-Z1271α an evaluation of their allelopathic potential

  摘要：

  Improved syntheses are described for nagilactone F and the antibiotic LL-Z1271 alpha, two of the most potent bioactive members of the podolactone family. The allelopathic potential of some members of this podolactone series has been evaluated, with the result that the metabolite LL-Z1271 alpha is one of the most active compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00355-5

文献信息

• Cambie, Richard C.; McNally, Heather M.; Robertson, John D., Australian Journal of Chemistry, 1984, vol. 37, # 2, p. 409 - 416
  作者：Cambie, Richard C.、McNally, Heather M.、Robertson, John D.、Rutledge, Peter S.、Woodgate, Paul D.

  DOI：——

  日期：——
• Cambie, Richard C.; Clark, George R.; Goeth, Michelle E., Australian Journal of Chemistry, 1989, vol. 42, # 4, p. 497 - 510
  作者：Cambie, Richard C.、Clark, George R.、Goeth, Michelle E.、Rickard, Clifton E.F.、Rutledge, Peter S.、et al.

  DOI：——

  日期：——
• 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.
• An Efficient Synthesis of the Antifungal Dilactone LL-Z1271α and of other Biologically Active Compounds
  作者：A Barrero

  DOI：10.1016/00404-0399(50)0949d-

  日期：1995.7.17
• CAMBIE, RICHARD C.;CLARK, GEORGE R.;GOETH, MICHELLE E.;RICKARD, CLIFTON E+, AUSTRAL. J. CHEM., 42,(1989) N, C. 497-509
  作者：CAMBIE, RICHARD C.、CLARK, GEORGE R.、GOETH, MICHELLE E.、RICKARD, CLIFTON E+

  DOI：——

  日期：——