(R)-2-[(1R,4aS,5R,8aR)-5-((S)-2-Iodo-1-methyl-ethyl)-3-methyl-7-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-methyl-butyric acid | 831221-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-[(1R,4aS,5R,8aR)-5-((S)-2-Iodo-1-methyl-ethyl)-3-methyl-7-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-methyl-butyric acid
• 英文别名: (2R)-2-[(1R,4aS,5R,8aR)-5-[(2S)-1-iodopropan-2-yl]-3-methyl-7-oxo-2,4a,5,6,8,8a-hexahydro-1H-naphthalen-1-yl]-3-methylbutanoic acid
• CAS: 831221-66-0
• 化学式: C₁₉H₂₉IO₃
• 分子量: 432.342
• InChiKey: WTSWCIARPBDBFM-WLGOAYHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-[(1R,4aS,5R,8aR)-5-((S)-2-Iodo-1-methyl-ethyl)-3-methyl-7-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-methyl-butyric acid 在 sodium tetrahydroborate 、 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.66h， 生成 2-[(1R,4aS,5R,7R,8aS)-7-Hydroxy-5-((S)-2-iodo-1-methyl-ethyl)-3-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-methyl-but-1-en-1-one
  参考文献：
  名称：

  Exploratory Studies Aimed at a Synthesis of Vinigrol. 3. Evaluation of a Lactone Bridge as a Conformational Lock

  摘要：

  DIAGRAMEvaluated in the present investigation are possible synthetic approaches to vinigrol based on the involvement of lactone rings as tools for the conformational rigidification of functionalized cis-octalins. Emphasis was placed on the structural arrangements resident in 3 and 5. The first of these systems proved to be highly strained and inaccessible. Especially notable was the finding that hydroxy ketenes 14 and 21 could be isolated and shown not to be amenable to cyclization when heated. The stereocontrolled assembly of 5 was successfully accomplished through exploitation of a related synthetic pathway. However, neither this attractive intermediate nor its close relative 33 could be processed in a manner that delivered the vinigrol framework. Nonetheless, several features of the routes deployed offer the prospect of wider application in other contexts.

  DOI：

  10.1021/jo0484575
• 作为产物：
  描述：

  (R)-2-[(1R,4aS,5R,8aR)-5-((S)-2-Iodo-1-methyl-ethyl)-3-methyl-7-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-methyl-butyraldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 乙腈 、 叔丁醇 为溶剂， 反应 2.0h， 以100%的产率得到(R)-2-[(1R,4aS,5R,8aR)-5-((S)-2-Iodo-1-methyl-ethyl)-3-methyl-7-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-methyl-butyric acid
  参考文献：
  名称：

  Exploratory Studies Aimed at a Synthesis of Vinigrol. 3. Evaluation of a Lactone Bridge as a Conformational Lock

  摘要：

  DIAGRAMEvaluated in the present investigation are possible synthetic approaches to vinigrol based on the involvement of lactone rings as tools for the conformational rigidification of functionalized cis-octalins. Emphasis was placed on the structural arrangements resident in 3 and 5. The first of these systems proved to be highly strained and inaccessible. Especially notable was the finding that hydroxy ketenes 14 and 21 could be isolated and shown not to be amenable to cyclization when heated. The stereocontrolled assembly of 5 was successfully accomplished through exploitation of a related synthetic pathway. However, neither this attractive intermediate nor its close relative 33 could be processed in a manner that delivered the vinigrol framework. Nonetheless, several features of the routes deployed offer the prospect of wider application in other contexts.

  DOI：

  10.1021/jo0484575