8β-hydroxyparthenolide acetate | 41059-80-7

• 物质功能分类: 天然产物 - 倍半萜
• 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: 8β-hydroxyparthenolide acetate
• 英文别名: lipiferolide；[(1S,2S,4R,7E,10R,11R)-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-10-yl] acetate
• CAS: 41059-80-7
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: ODYJJNFWFYUXSS-SOZNHUOKSA-N

物化性质

• 沸点：
  444.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8β-hydroxyparthenolide acetate 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以69%的产率得到Acetic acid (E)-(3aR,4R,11S,11aS)-10-fluoro-11-hydroxy-6,10-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,8,9,10,11,11a-decahydro-cyclodeca[b]furan-4-yl ester
  参考文献：
  名称：

  Acid cyclization and other products of the germacranolide epoxide, lipiferolide

  摘要：

  DOI：

  10.1021/jo00171a019
• 作为产物：
  描述：

  inulasalsolin 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以70 mg的产率得到8β-hydroxyparthenolide acetate
  参考文献：
  名称：

  Sesquiterpene Lactones and Thymol Esters from Vicoa pentanema

  摘要：

  The aerial parts of Vicoa pentanema yielded four new sesquiterpene lactones, namely, 10 alpha-hydroxy-14H-inuviscolide (1), 4 alpha,5 alpha-epoxy-10 alpha,11 beta,13H,14H-1-epi-inuviscolide 3-beta-D-glucoside (2), 2 alpha-O-acetyl-3 beta-hydroxyalantolactone (3), and 2 alpha,3 alpha-dihydroxyalloalantolactone (4). The structure and stereochemical assignments of all sesquiterpenes were based on their IH and C-13-NMR spectral data, including those derived from 2D-NMR COSY, HETCOR, FLOCK, and NOESY experiments, as well as extensive NOE-difference studies. In addition, the same plant material yielded the known sesquiterpene lactones 8 beta-hydroxyparthenolide (5), 8-epi-confertin (6), 4 alpha,5 alpha-epoxy-10 alpha,14H-1-epi-inuviscolide (7), inuviscolide (8), lipiferolide (9), and carabrone (PQ), the known thymol ester 7,8-epoxy-9-(isobutyryloxy)thymolisobutyrate (11), and its hydrolysis product 7-hydroxy-8,9-bis(isobutyryloxy)thymol (12).

  DOI：

  10.1021/np960506o

文献信息

• Sesquiterpene Lactones and Thymol Esters from <i>Vicoa pentanema</i>
  作者：Jaber S. Mossa、Farouk S. El-Feraly、Ilias Muhammad、Kyaw Zaw、Zakaria H. Mbwambo、John M. Pezzuto、Harry H. S. Fong

  DOI：10.1021/np960506o

  日期：1997.6.1

  The aerial parts of Vicoa pentanema yielded four new sesquiterpene lactones, namely, 10 alpha-hydroxy-14H-inuviscolide (1), 4 alpha,5 alpha-epoxy-10 alpha,11 beta,13H,14H-1-epi-inuviscolide 3-beta-D-glucoside (2), 2 alpha-O-acetyl-3 beta-hydroxyalantolactone (3), and 2 alpha,3 alpha-dihydroxyalloalantolactone (4). The structure and stereochemical assignments of all sesquiterpenes were based on their IH and C-13-NMR spectral data, including those derived from 2D-NMR COSY, HETCOR, FLOCK, and NOESY experiments, as well as extensive NOE-difference studies. In addition, the same plant material yielded the known sesquiterpene lactones 8 beta-hydroxyparthenolide (5), 8-epi-confertin (6), 4 alpha,5 alpha-epoxy-10 alpha,14H-1-epi-inuviscolide (7), inuviscolide (8), lipiferolide (9), and carabrone (PQ), the known thymol ester 7,8-epoxy-9-(isobutyryloxy)thymolisobutyrate (11), and its hydrolysis product 7-hydroxy-8,9-bis(isobutyryloxy)thymol (12).
• Acid cyclization and other products of the germacranolide epoxide, lipiferolide
  作者：John H. Wilton、Raymond W. Doskotch

  DOI：10.1021/jo00171a019

  日期：1983.11