(1R,2S,6R,7R,9R,12S)-6-((R)-1-Hydroxymethyl-2-methyl-propyl)-4,12-dimethyl-10-oxa-tricyclo[7.3.1.0^2,7]tridec-3-en-11-one | 831221-84-2

• 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: (1R,2S,6R,7R,9R,12S)-6-((R)-1-Hydroxymethyl-2-methyl-propyl)-4,12-dimethyl-10-oxa-tricyclo[7.3.1.0^2,7]tridec-3-en-11-one
• 英文别名: (1R,2S,6R,7R,9R,12S)-6-[(2R)-1-hydroxy-3-methylbutan-2-yl]-4,12-dimethyl-10-oxatricyclo[7.3.1.02,7]tridec-3-en-11-one
• CAS: 831221-84-2
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: FONLMXFPPIOLPS-FPMLTQPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  (1R,2S,6R,7R,9R,12S)-6-((R)-1-Hydroxymethyl-2-methyl-propyl)-4,12-dimethyl-10-oxa-tricyclo[7.3.1.0^2,7]tridec-3-en-11-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到(R)-2-((1R,2S,6R,7R,9R,12S)-4,12-Dimethyl-11-oxo-10-oxa-tricyclo[7.3.1.0^2,7]tridec-3-en-6-yl)-3-methyl-butyraldehyde
  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：

  (S)-2-{(1R,4aR,5R,8aS)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-3-hydroxy-7-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl}-propionic acid 在 2-氯-1-甲基吡啶碘化物 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 (1R,2S,6R,7R,9R,12S)-6-((R)-1-Hydroxymethyl-2-methyl-propyl)-4,12-dimethyl-10-oxa-tricyclo[7.3.1.0^2,7]tridec-3-en-11-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