(3aR,4R,4aR,5R,7aR,8S,8aS)-2,2,4,6,6-pentamethyl-3a,4a,5,6,7,7a,8,8a-octahydro-4H-4,8-ethenoindeno[5,6-d][1,3]dioxol-5-yl acetate | 1253199-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,4aR,5R,7aR,8S,8aS)-2,2,4,6,6-pentamethyl-3a,4a,5,6,7,7a,8,8a-octahydro-4H-4,8-ethenoindeno[5,6-d][1,3]dioxol-5-yl acetate
• CAS: 1253199-45-9
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: HCVRUZBPXWNXBA-RGMIFFJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aR,4R,4aR,5R,7aR,8S,8aS)-2,2,4,6,6-pentamethyl-3a,4a,5,6,7,7a,8,8a-octahydro-4H-4,8-ethenoindeno[5,6-d][1,3]dioxol-5-yl acetate 在 4-二甲氨基吡啶 、 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以90%的产率得到[(1R,2R,3R,6R,7S,10R,11S)-10,11-dihydroxy-1,4,4-trimethyl-3-tricyclo[5.2.2.02,6]undec-8-enyl] acetate
  参考文献：
  名称：

  A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene

  摘要：

  The first total synthesis of the hirsutene-type sesquiterpenoid natural product (+)-connatusin B (2) is reported. The cis-1,2-dihydrocatechol 3, which is obtained in enantiomerically pure form via the enzymatic dihydroxylation of toluene, served as the starting material. Diels-Alder cycloaddition and oxa-di-pi-methane rearrangement reactions represent key chemical steps in the reaction sequence leading to the cyclopropane ring-fused linear triquinane 14. Reductive cleavage of the three-membered ring within this framework and various functional group interconversions then provide the title compound 2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.059
• 作为产物：
  描述：

  (3aR,4R,4aR,5R,7aR,8S,8aS)-2,2,4,6,6-pentamethyl-3a,4a,5,6,7,7a,8,8a-octahydro-4H-4,8-ethenoindeno[5,6-d][1,3]dioxol-5-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 16.0h， 以99%的产率得到(3aR,4R,4aR,5R,7aR,8S,8aS)-2,2,4,6,6-pentamethyl-3a,4a,5,6,7,7a,8,8a-octahydro-4H-4,8-ethenoindeno[5,6-d][1,3]dioxol-5-yl acetate
  参考文献：
  名称：

  A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene

  摘要：

  The first total synthesis of the hirsutene-type sesquiterpenoid natural product (+)-connatusin B (2) is reported. The cis-1,2-dihydrocatechol 3, which is obtained in enantiomerically pure form via the enzymatic dihydroxylation of toluene, served as the starting material. Diels-Alder cycloaddition and oxa-di-pi-methane rearrangement reactions represent key chemical steps in the reaction sequence leading to the cyclopropane ring-fused linear triquinane 14. Reductive cleavage of the three-membered ring within this framework and various functional group interconversions then provide the title compound 2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.059