[(1S,2R,4S,5S,7S,11S)-5,11-dimethyl-8-oxo-2-tetracyclo[5.3.1.11,4.05,11]dodecanyl] benzoate | 874658-40-9

• 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: [(1S,2R,4S,5S,7S,11S)-5,11-dimethyl-8-oxo-2-tetracyclo[5.3.1.11,4.05,11]dodecanyl] benzoate
• CAS: 874658-40-9
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: DFRWPWRMCFOLSL-IXQRCOMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4S,5S,7S,11S)-5,11-dimethyl-8-oxo-2-tetracyclo[5.3.1.11,4.05,11]dodecanyl] benzoate 在 三甲基氯硅烷 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.0h， 生成 (1R,2R,4S,5S,7S,10R,11S)-5,10,11-trimethyl-8-oxotetracyclo[5.3.1.1^1,4.0^5,11]dodec-2-yl benzoate
  参考文献：
  名称：

  Enantiospecific first total synthesis of (+)-2β-hydroxysolanascone, the aglycone of the phytoalexin isolated from flue-cured tobacco leaves

  摘要：

  The first total synthesis of (+)-2 beta-hydroxysolanascone, the aglycone of the phytoalexin 2 beta-hydroxysolanascone-beta-glucopyranoside isolated from flue-cured tobacco leaves (N. tabacian L., OCL), and its 2,10-diepi- and 2 alpha-epimers has been accomplished, starting from the readily available monoterpene (R)-carvone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.014
• 作为产物：
  描述：

  Benzoic acid (1R,3S,5S)-3-isopropenyl-6-methyl-8-oxo-spiro[4.5]dec-6-en-1-yl ester 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到[(1S,2R,4S,5S,7S,11S)-5,11-dimethyl-8-oxo-2-tetracyclo[5.3.1.11,4.05,11]dodecanyl] benzoate
  参考文献：
  名称：

  Enantiospecific first total synthesis of (+)-2β-hydroxysolanascone, the aglycone of the phytoalexin isolated from flue-cured tobacco leaves

  摘要：

  The first total synthesis of (+)-2 beta-hydroxysolanascone, the aglycone of the phytoalexin 2 beta-hydroxysolanascone-beta-glucopyranoside isolated from flue-cured tobacco leaves (N. tabacian L., OCL), and its 2,10-diepi- and 2 alpha-epimers has been accomplished, starting from the readily available monoterpene (R)-carvone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.014

文献信息

• Enantiospecific first total synthesis of (+)-2β-hydroxysolanascone, the aglycone of the phytoalexin isolated from flue-cured tobacco leaves
  作者：A. Srikrishna、S.S.V. Ramasastry

  DOI：10.1016/j.tetlet.2005.11.014

  日期：2006.1

  The first total synthesis of (+)-2 beta-hydroxysolanascone, the aglycone of the phytoalexin 2 beta-hydroxysolanascone-beta-glucopyranoside isolated from flue-cured tobacco leaves (N. tabacian L., OCL), and its 2,10-diepi- and 2 alpha-epimers has been accomplished, starting from the readily available monoterpene (R)-carvone. (c) 2005 Elsevier Ltd. All rights reserved.