[1-(4,4-dimethyl-2-prop-1-en-2-ylcyclopentyl)-2-methylbut-3-yn-2-yl] formate | 220810-49-1

• 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: [1-(4,4-dimethyl-2-prop-1-en-2-ylcyclopentyl)-2-methylbut-3-yn-2-yl] formate
• CAS: 220810-49-1
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: WNRRUEDKMDZFIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [1-(4,4-dimethyl-2-prop-1-en-2-ylcyclopentyl)-2-methylbut-3-yn-2-yl] formate 在 palladium diacetate 、 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 生成 4,4-dimethyl-2-isopropenyl-1-(2-methylene-3-butenyl)cyclopentane 、 4,4-dimethyl-2-isopropenyl-1-(2-methylene-3-butenyl)cyclopentane
  参考文献：
  名称：

  Synthetic Studies towards Delta6-Protoilludene. A Formal Synthesis.

  摘要：

  A synthetic strategy towards Delta(6)-protoilludene included an intramolecular allene-ene cycloaddition reaction as a key step; however, the thermal reaction furnished a stereoisomeric mixture of 9-methyl-1,4,4,8-tetramethyltricyclo[6.2.0.0(2,6)]decane, which has a ring assembly isomeric with that of the target molecule. Another approach to Delta(6)-protoilludene required cis-4,4-dimethyl-2-isopropenylcyclopentylacetic acid, which was obtained from the mixture of stereoisomers by column chromatographic separation of the corresponding iodolactones. The cis-acid was further converted into cis-ethyl 4-(2-isopropenyl-4,4-dimethylcyclopentyl)-3-methyl-2-butenoate which has previously been transformed by others into Delta(6)-protoilludene. Hence, our approach constitutes formally a new synthesis of Delta(6)-protoilludene.

  DOI：

  10.3891/acta.chem.scand.52-1373
• 作为产物：
  描述：

  1-(2-oxopropyl)-4,4-dimethyl-2-isopropenyl cyclopentane 在 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 30.5h， 生成 [1-(4,4-dimethyl-2-prop-1-en-2-ylcyclopentyl)-2-methylbut-3-yn-2-yl] formate
  参考文献：
  名称：

  Synthetic Studies towards Delta6-Protoilludene. A Formal Synthesis.

  摘要：

  A synthetic strategy towards Delta(6)-protoilludene included an intramolecular allene-ene cycloaddition reaction as a key step; however, the thermal reaction furnished a stereoisomeric mixture of 9-methyl-1,4,4,8-tetramethyltricyclo[6.2.0.0(2,6)]decane, which has a ring assembly isomeric with that of the target molecule. Another approach to Delta(6)-protoilludene required cis-4,4-dimethyl-2-isopropenylcyclopentylacetic acid, which was obtained from the mixture of stereoisomers by column chromatographic separation of the corresponding iodolactones. The cis-acid was further converted into cis-ethyl 4-(2-isopropenyl-4,4-dimethylcyclopentyl)-3-methyl-2-butenoate which has previously been transformed by others into Delta(6)-protoilludene. Hence, our approach constitutes formally a new synthesis of Delta(6)-protoilludene.

  DOI：

  10.3891/acta.chem.scand.52-1373