(4R,4aS,8R,8aR)-8-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-4-((S)-2-hydroxy-1-methyl-ethyl)-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one | 831221-62-6

• 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: (4R,4aS,8R,8aR)-8-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-4-((S)-2-hydroxy-1-methyl-ethyl)-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one
• 英文别名: (4R,4aS,8R,8aR)-8-[(2R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbutan-2-yl]-4-[(2S)-1-hydroxypropan-2-yl]-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one
• CAS: 831221-62-6
• 化学式: C₂₅H₄₆O₃Si
• 分子量: 422.724
• InChiKey: IISQOBUIADTPRR-GBVUVUFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,4aS,8R,8aR)-8-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-4-((S)-2-hydroxy-1-methyl-ethyl)-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one 在 咪唑 、 盐酸 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 碘 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 6.08h， 生成 (R)-2-[(1R,4aS,5R,7R,8aR)-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-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
• 作为产物：
  描述：

  (4R,4aS,8R,8aR)-8-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-4-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-one 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到(4R,4aS,8R,8aR)-8-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-4-((S)-2-hydroxy-1-methyl-ethyl)-6-methyl-3,4,4a,7,8,8a-hexahydro-1H-naphthalen-2-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

文献信息

• Exploratory Studies Aimed at a Synthesis of Vinigrol. 3. Evaluation of a Lactone Bridge as a Conformational Lock
  作者：Leo A. Paquette、Ivan Efremov

  DOI：10.1021/jo0484575

  日期：2005.1.1

  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.