4α,5α-epoxy-10α,14-dihydro-1-epi-inuviscolide | 68776-54-5

• 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: 4α,5α-epoxy-10α,14-dihydro-1-epi-inuviscolide
• 英文别名: 4α,5α-epoxy-10α,14H-dihydro-1-epi-inuviscolide；4α,5α-epoxy-10α,14H-1-epi-inuviscolide；4α,5α-epoxy-10αH-1-epiinuviscolide；(1S,3R,7S,9S,10S,13R)-9,13-dimethyl-4-methylidene-6,14-dioxatetracyclo[8.4.0.01,13.03,7]tetradecan-5-one
• CAS: 68776-54-5
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: AIHKZOVNPAYCEL-KYHCNFOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4α,5α-epoxy-10α,14-dihydro-1-epi-inuviscolide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80 mg的产率得到4α(5α),11α(13)-diepoxy-10α,11β,14H-1-epi-inuvicolide
  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
• 作为产物：
  描述：

  (1R,3S,5R,8Z,11S)-5,9-dimethyl-14-methylidene-4,12-dioxatricyclo[9.3.0.03,5]tetradec-8-en-13-one 以1%的产率得到
  参考文献：
  名称：

  ORTEGA, ALFREDO;MALDONADO, EMMA, HETEROCYCLES, 29,(1989) N, C. 635-638

  摘要：

  DOI：

文献信息

• ORTEGA, ALFREDO;MALDONADO, EMMA, HETEROCYCLES, 29,(1989) N, C. 635-638
  作者：ORTEGA, ALFREDO、MALDONADO, EMMA

  DOI：——

  日期：——
• 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).