[(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 | 1253199-46-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(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
• CAS: 1253199-46-0
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: DOARDMKVAYDRPJ-ZTIYUSGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(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 在 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以94%的产率得到
  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-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