3-{1(S)-hydroxy-2-[(4aS,5R,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,1,4a-trimethyl-5-naphthjyl]ethyl}furan | 201993-64-8

• 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: 3-{1(S)-hydroxy-2-[(4aS,5R,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,1,4a-trimethyl-5-naphthjyl]ethyl}furan
• 英文别名: (1S)-2-[(1R,2R,4aS,8aS)-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]-1-(furan-3-yl)ethanol
• CAS: 201993-64-8
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: AZYJFNYLJPMWBR-GCLMUHHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  45.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-{1(S)-hydroxy-2-[(4aS,5R,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,1,4a-trimethyl-5-naphthjyl]ethyl}furan 在 对甲苯磺酸 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(2S,3aR,5aS,9aS,9bR)-2-(3-furyl)-1,2,3a,4,5,5a,6,7,8,9,9a,9b-dodecahydro-3a-hydroxymethyl-6,6,9a-trimethyl-trans-naphtho[2,1-b]furan
  参考文献：
  名称：

  Synthesis of Acuminolide and 17-O-Acetylacuminolide from (+)-Sclareolide

  摘要：

  The synthesis of natural acuminolide and 17-O-acetylacuminolide is reported, Commerically available (+)-sclareolide was converted to epoxy alcohol 3, which upon acid-catalyzed cyclization afforded tricycle 14. Reaction of 14 with O-1(2) in the presence of a hindered base gave an inseparable mixture of acuminolide 1a and 16-epiacuminolide 1b in a 70:30 ratio. Chromatographic separation of the diacetates of 1a and 1b afforded pure 18a and 18b, An analogous reaction sequence was used in the synthesis of 17-O-acetylacuminolide (2a) and 16-epi-17-O-acetylacuminolide (2b).

  DOI：

  10.1021/jo971631n
• 作为产物：
  描述：

  香紫苏二醇 在 4-二甲氨基吡啶 、 正丁基锂 、 dipyridine chromium trioxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-{1(S)-hydroxy-2-[(4aS,5R,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,1,4a-trimethyl-5-naphthjyl]ethyl}furan
  参考文献：
  名称：

  Synthesis of Acuminolide and 17-O-Acetylacuminolide from (+)-Sclareolide

  摘要：

  The synthesis of natural acuminolide and 17-O-acetylacuminolide is reported, Commerically available (+)-sclareolide was converted to epoxy alcohol 3, which upon acid-catalyzed cyclization afforded tricycle 14. Reaction of 14 with O-1(2) in the presence of a hindered base gave an inseparable mixture of acuminolide 1a and 16-epiacuminolide 1b in a 70:30 ratio. Chromatographic separation of the diacetates of 1a and 1b afforded pure 18a and 18b, An analogous reaction sequence was used in the synthesis of 17-O-acetylacuminolide (2a) and 16-epi-17-O-acetylacuminolide (2b).

  DOI：

  10.1021/jo971631n

文献信息

• Synthesis of Acuminolide and 17-<i>O</i>-Acetylacuminolide from (+)-Sclareolide
  作者：Phillip A. Zoretic、Haiquan Fang、Anthony A. Ribeiro、George Dubay

  DOI：10.1021/jo971631n

  日期：1998.2.1

  The synthesis of natural acuminolide and 17-O-acetylacuminolide is reported, Commerically available (+)-sclareolide was converted to epoxy alcohol 3, which upon acid-catalyzed cyclization afforded tricycle 14. Reaction of 14 with O-1(2) in the presence of a hindered base gave an inseparable mixture of acuminolide 1a and 16-epiacuminolide 1b in a 70:30 ratio. Chromatographic separation of the diacetates of 1a and 1b afforded pure 18a and 18b, An analogous reaction sequence was used in the synthesis of 17-O-acetylacuminolide (2a) and 16-epi-17-O-acetylacuminolide (2b).