9-oxo-6α(H),7α(H)-eudesm-4(5),11(13)-dien-12,6-olide | 111420-61-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-oxo-6α(H),7α(H)-eudesm-4(5),11(13)-dien-12,6-olide
• 英文别名: 9-oxo-tournefolide；tourneforin；(3aS,5aS,9bR)-5a,9-dimethyl-3-methylidene-3a,4,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-2,5-dione
• CAS: 111420-61-2
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: CPHPAWJXZHHPEN-PSOPSSQASA-N

物化性质

• 沸点：
  430.2±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-oxo-6α(H),7α(H)-eudesm-4(5),11(13)-dien-12,6-olide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以94%的产率得到(3R,3aS,5S,5aS,9bR)-5-Hydroxy-3,5a,9-trimethyl-3a,4,5,5a,6,7,8,9b-octahydro-3H-naphtho[1,2-b]furan-2-one
  参考文献：
  名称：

  Carbon-13 NMR spectroscopy of sesquiterpenes. 3. Synthesis and carbon-13 NMR spectral data of 4.alpha.,5.alpha.- and 4.beta.,5.beta.-epoxyeudesmanolides. Configuration and .gamma. effect of the oxirane ring

  摘要：

  The epoxide eudesmanolides 14-21, which constitute epimeric pairs with respect to the configuration of the oxirane ring, have been synthesized in a stereochemically unambiguous way. Comparison of their C-12 NMR spectra with those of the parent olefins 10-13 does not, however, reveal any significant correlation between the configuration of the oxirane ring and the shifts undergone by the signals of the gamma carbon atoms C-1/C-2/C-7/C-9/C-14.

  DOI：

  10.1021/jo00029a006

文献信息

• Synthetic transformations of sesquiterpene lactones. V.* Synthesis and cytotoxicity of 13-aryl-substituted tourneforin derivatives
  作者：E. E. Shulˈts、S. S. Patrushev、A. V. Belovodskii、M. M. Shakirov、T. V. Rybalova、A. G. Pokrovskii、M. A. Pokrovskii、G. A. Tolstikov、S. M. Adekenov

  DOI：10.1007/s10600-012-0214-4

  日期：2012.5

  13-Aryl-substituted tourneforin derivatives were synthesized via the Heck reaction with aryliodides. The structure of (E)-13-(3,4-dimethoxybenzyl)-eudesma-4(5),11(13)-dien-6α,12-olide was confirmed by an XSA. A study of the cytotoxicity of the synthesized derivatives for CEM-13, MT-4, and U-937 tumor models showed promise for the modification.

  通过与芳基碘化物的 Heck 反应合成了 13-芳基取代的 tourneforin 衍生物。XSA证实了(E)-13-(3,4-二甲氧基苄基)-eudesma-4(5),11(13)-dien-6α,12-olide的结构。对合成衍生物对 CEM-13、MT-4 和 U-937 肿瘤模型的细胞毒性进行的研究表明，这种改性是有希望的。
• Epoxidation of sesquiterpene lactones tourneforin and ludartin
  作者：R. I. Dzhalmakhanbetova、M. A. Rodichev、Yu. V. Gatilov、M. M. Shakirov、G. A. Atazhanova、S. M. Adekenov

  DOI：10.1007/s10600-009-9399-6

  日期：2009.7

  Epoxy derivatives of the sesquiterpene lactones ludartin and tourneforin were synthesized. Their structures were elucidated using spectral data and x-ray structure analysis.

  合成了倍半萜内酯鲁达亭（ludartin）和土荆皮（tourneforin）的环氧衍生物。利用光谱数据和 X 射线结构分析阐明了它们的结构。
• Sanz, Juan Francisco; Marco, Juan Alberto, Liebigs Annalen der Chemie, 1990, # 6, p. 541 - 545
  作者：Sanz, Juan Francisco、Marco, Juan Alberto

  DOI：——

  日期：——
• Carbon-13 NMR spectroscopy of sesquiterpenes. 3. Synthesis and carbon-13 NMR spectral data of 4.alpha.,5.alpha.- and 4.beta.,5.beta.-epoxyeudesmanolides. Configuration and .gamma. effect of the oxirane ring
  作者：Miguel Carda、Juan F. Sanz、J. Alberto Marco

  DOI：10.1021/jo00029a006

  日期：1992.1

  The epoxide eudesmanolides 14-21, which constitute epimeric pairs with respect to the configuration of the oxirane ring, have been synthesized in a stereochemically unambiguous way. Comparison of their C-12 NMR spectra with those of the parent olefins 10-13 does not, however, reveal any significant correlation between the configuration of the oxirane ring and the shifts undergone by the signals of the gamma carbon atoms C-1/C-2/C-7/C-9/C-14.