methyl (2S,2aR,2bS,4S,5aR,6S,6aR)-decahydro-2-hydroxy-4,6-dimethyl-2,6-methanocyclobuta[a]pentalene-4-carboxylate | 914089-13-7

• 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: methyl (2S,2aR,2bS,4S,5aR,6S,6aR)-decahydro-2-hydroxy-4,6-dimethyl-2,6-methanocyclobuta[a]pentalene-4-carboxylate
• 英文别名: methyl (1S,2R,3R,5S,7S,8R,10S)-5-hydroxy-7,10-dimethyltetracyclo[6.3.0.02,5.03,7]undecane-10-carboxylate
• CAS: 914089-13-7
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: IUFPARANRFBFQA-LJWSOQGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  methyl (2S,2aR,2bS,4S,5aR,6S,6aR)-decahydro-2-hydroxy-4,6-dimethyl-2,6-methanocyclobuta[a]pentalene-4-carboxylate 、 4-硝基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到methyl (2S,2aR,2bS,4S,5aR,6S,6aR)-decahydro-4,6-dimethyl-2-[(4-nitrobenzoyl)oxy]-2,6-methanocyclobuta[a]pentalene-4-carboxylate
  参考文献：
  名称：

  Chemoenzymatic syntheses of the linear triquinane-type sesquiterpenes (+)-hirsutic acid and (−)-complicatic acid

  摘要：

  Formal total syntheses of the natural enantiomeric forms of the title sesquiterpenes 1 and 2 have been achieved using, as starting material, the readily available and enantiomerically pure cis-1,2-dihydrocatechol 4 derived from the whole-cell biotransformation of toluene. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.145
• 作为产物：
  描述：

  methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate 在 samarium diiodide 、 苯乙酮 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 36.0h， 生成 methyl (2S,2aR,2bS,4S,5aR,6S,6aR)-decahydro-2-hydroxy-4,6-dimethyl-2,6-methanocyclobuta[a]pentalene-4-carboxylate
  参考文献：
  名称：

  Chemoenzymatic total syntheses of the linear triquinane-type natural products (+)-hirsutic acid and (−)-complicatic acid from toluene

  摘要：

  Total syntheses of title natural products, 1 and 2, have been achieved using the cis-1,2-dihydrocatechol 7 as starting material. Compound 7 is readily obtained in large quantity and enantiomerically pure form through the whole-cell biotransformation of toluene using the genetically engineered micro-organism Escherichia coli JM109 (pDTG601) that over-expresses the enzyme toluene dioxygenase (TDO). Three key chemical steps were employed in these syntheses, the first of which was a high-pressure- promoted Diels-Alder cycloaddition reaction between diene 8 and cyclopentenone to give adduct 9. The second key step was the photochemically promoted oxa-di-pi-methane rearrangement of the bicyclo[2.2.2] octenone derivative, 18, of 9 to give 20 while the third key step was the reductive cleavage of the last compound so as to afford the linear triquinane 22. Elaboration of compound 22 to targets 1 and 2 followed conventional and/or established procedures. Single-crystal X-ray analyses were carried out on compounds 10-13, 15, 18, 24, and 34. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.073