(1R,2R,3R)-1-异丙烯基-2-[(甲氧基甲氧基)甲基]-3-甲基环戊烷 | 528878-78-6

• 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
• 中文名称: (1R,2R,3R)-1-异丙烯基-2-[(甲氧基甲氧基)甲基]-3-甲基环戊烷
• 英文名称: (1R,2R,3R)-1-isopropenyl-2-methoxymethoxymethyl-3-methylcyclopentane
• 英文别名: (1R,2R,3R)-2-(methoxymethoxymethyl)-1-methyl-3-prop-1-en-2-ylcyclopentane
• CAS: 528878-78-6
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: XTJRULYOOFCEDD-GRYCIOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R)-1-异丙烯基-2-[(甲氧基甲氧基)甲基]-3-甲基环戊烷 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium cyclohexylisopropyl amide 、 四丁基氟化铵 、 碘 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 碳酸氢钠 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 2.5h， 生成 (3R,3aS,4R,7S,7aR,1'R,2'R,5'R)-3-methoxymethoxymethyl-3-[{2'-(1''-(methoxymethoxymethyl)vinyl)-5'-methylcyclopentyl}methyl]-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoinden-1-one
  参考文献：
  名称：

  Total Synthesis of Sordaricin

  摘要：

  The total synthesis of sordaricin, the diterpene aglycone of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton of the target molecule. A second approach using a tandem cycloreversion/intramolecular [4 + 2] cycloaddition sequence is also detailed.

  DOI：

  10.1021/ol0342599
• 作为产物：
  描述：

  (2S,3R,4R)-thiocarbonic acid O-(4-isopropenyl-3-methoxymethoxymethyl-2-methylcyclopentyl) ester O-phenyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.5h， 以100%的产率得到(1R,2R,3R)-1-异丙烯基-2-[(甲氧基甲氧基)甲基]-3-甲基环戊烷
  参考文献：
  名称：

  Total Synthesis of Sordaricin

  摘要：

  An enantioconvergent total synthesis of sordaricin (3), the diterpene aglycon of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton of the target molecule as a single regioisomer 30. A second approach employed a tandem cycloreversion/intramolecular [4 + 2] cycloaddition process to afford not only the desired product 30 but also significant quantities of the undesired regioisomer iso-30. An investigation into the reasons for the difference in regioselectivity between these two reactions revealed the intervention of a cycloreversion/cycloaddition pathway at elevated temperatures leading to the formation of iso-30. Experimental evidence supports the hypothesis that iso-30 is the more thermodynamically stable of the two regioisomers.

  DOI：

  10.1021/jo048199b

文献信息

• Total Synthesis of Sordaricin
  作者：Lewis N. Mander、Regan J. Thomson

  DOI：10.1021/jo048199b

  日期：2005.3.1

  An enantioconvergent total synthesis of sordaricin (3), the diterpene aglycon of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton of the target molecule as a single regioisomer 30. A second approach employed a tandem cycloreversion/intramolecular [4 + 2] cycloaddition process to afford not only the desired product 30 but also significant quantities of the undesired regioisomer iso-30. An investigation into the reasons for the difference in regioselectivity between these two reactions revealed the intervention of a cycloreversion/cycloaddition pathway at elevated temperatures leading to the formation of iso-30. Experimental evidence supports the hypothesis that iso-30 is the more thermodynamically stable of the two regioisomers.