2-[(1aR,3aS,7aS,7bS)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]ethanol | 201993-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 2-[(1aR,3aS,7aS,7bS)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]ethanol
• CAS: 201993-67-1
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: SRDBLBAJSJOVRS-HNKHHVNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1aR,3aS,7aS,7bS)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]ethanol 在 吡啶 、 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (5S,8R,10S)-9-(2-acetoxyethyl)-austrodor-9-one
  参考文献：
  名称：

  Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid

  摘要：

  An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.024
• 作为产物：
  描述：

  香紫苏二醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-[(1aR,3aS,7aS,7bS)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]ethanol
  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 and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid
  作者：Veaceslav Kulcitki、Nicon Ungur、Margherita Gavagnin、Marianna Carbone、Guido Cimino

  DOI：10.1016/j.tetasy.2003.10.024

  日期：2004.2

  An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.
• 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).