(-)-3α,4α-epoxy-10α-hydroxy-1,5,7αH,6,11βH-guaian-6,12-olide | 474499-99-5

• 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: (-)-3α,4α-epoxy-10α-hydroxy-1,5,7αH,6,11βH-guaian-6,12-olide
• 英文别名: (1S,2S,5S,6S,9R,10R,12R,14S)-9-hydroxy-5,9,14-trimethyl-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradecan-4-one
• CAS: 474499-99-5
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: XHNMTDKGSOUWJJ-HHYLIOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-3α,4α-epoxy-10α-hydroxy-1,5,7αH,6,11βH-guaian-6,12-olide 在 吡啶 、 sodium tetrahydroborate 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3β-phenylselenyl-4α-hydroxy-5,7αH,6,11βH-guai-1(10)-en-6,12-olide
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-11βH,13-Dihydroestafiatin, (+)-11βH,13-Dihydroludartin, (−)-Compressanolide, and (−)-11βH,13-Dihydromicheliolide from Santonin

  摘要：

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.

  DOI：

  10.1021/np020109f
• 作为产物：
  描述：

  (3S,3aS,6R,6aR,9aR,9bS)-6-hydroxy-3,6,9-trimethyl-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以74%的产率得到(-)-3α,4α-epoxy-10α-hydroxy-1,5,7αH,6,11βH-guaian-6,12-olide
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-11βH,13-Dihydroestafiatin, (+)-11βH,13-Dihydroludartin, (−)-Compressanolide, and (−)-11βH,13-Dihydromicheliolide from Santonin

  摘要：

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.

  DOI：

  10.1021/np020109f