dimethyl 8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioate | 81800-51-3

• 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 8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioate
• 英文别名: ((4aR)-5t-methoxycarbonyl-5c,8a-dimethyl-2-oxo-(4ar,8at)-decahydro-[1t]naphthyl)-acetic acid methyl ester；((4aR)-5t-Methoxycarbonyl-5c,8a-dimethyl-2-oxo-(4ar,8at)-decahydro-[1t]naphthyl)-essigsaeure-methylester；((4aR)-2-Oxo-5c,8at-dimethyl-5t-methoxycarbonyl-(4arH)-decahydro-naphthyl-(1t))-essigsaeure-methylester；19-Methoxycarbonyl-8-oxo-13,14,15,16,17-pentanorlabdan-12-saeuremethylester；8-Oxo-(13->17)pentanorlabdan-12.19-disaeure-dimethylester；methyl (1S,4aS,5R,8aR)-5-(2-methoxy-2-oxoethyl)-1,4a-dimethyl-6-oxo-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 81800-51-3
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: PFGNKHWISJVOOT-AADNMHCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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-pentanorlabdane-12,19-dioate 在 吡啶 、 硫酸 、 溴 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 2.25h， 生成 12,8 lactone of 7α-acetoxy-11-bromo-8-hydroxy-13,14,15,16,17-pentanorlabd-8-ene-12,19-dioic acid
  参考文献：
  名称：

  Cambie, Richard C.; Robertson, John D.; Rutledge, Peter S., Australian Journal of Chemistry, 1982, vol. 35, # 1, p. 183 - 195

  摘要：

  DOI：
• 作为产物：
  描述：

  罗汉松酸 在 palladium on activated charcoal 、 臭氧 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 24.17h， 生成 dimethyl 8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioate
  参考文献：
  名称：

  Cambie, Richard C.; Robertson, John D.; Rutledge, Peter S., Australian Journal of Chemistry, 1982, vol. 35, # 1, p. 183 - 195

  摘要：

  DOI：

文献信息

• Chemistry of the natural order cupressales—41
  作者：V.P. Arya、H. Erdtman、T. Kubota

  DOI：10.1016/0040-4020(61)80076-8

  日期：1961.1

  A new diterpene acid, communic acid, has been isolated as its sodium salt from the bark of the common juniper, Juniperus communis L. The structure and configuration (1a) of this acid follows from direct correlations with torulosol and with agathene dicarboxylic acid as well as from the results of degradation experiments.

  从普通杜松（Juniperus communis L）的树皮中分离出一种新的二萜酸，其酸为钠盐。该酸的结构和构型（1a）来源于与甲苯酚和与邻苯二酚二羧酸的直接相关性。根据降解实验的结果。
• Zur Kenntnis der Diterpene. (45. Mitteilung). Über den Abbau der Agathen-disäure mit Ozon
  作者：L. Ruzicka、E. Bernold、A. Tallichet

  DOI：10.1002/hlca.19410240131

  日期：——
• 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：——
• 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.