(3R)-9-acetyl-8a-hydroxy-3-isopropenyl-10a-methyldodecahydro-1(2H)-phenanthrenone

• 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: (3R)-9-acetyl-8a-hydroxy-3-isopropenyl-10a-methyldodecahydro-1(2H)-phenanthrenone
• 英文别名: 8-Acetyl-7-hydroxy-3-isopropenyl-10-methylperhydrophenanthren-1-one；(3R,4aS,4bS,8aS,9R,10aS)-9-acetyl-8a-hydroxy-10a-methyl-3-prop-1-en-2-yl-3,4,4a,4b,5,6,7,8,9,10-decahydro-2H-phenanthren-1-one
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: QFINPYOYQJOXAF-YLQUGHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-{(5R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-isopropenyl-2-methyl-2-cyclohexen-1-yl}cyclohexanone 、 丁烯酮 在 triphenylmethylium hexachloroantimonate(V) 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(3R)-9-acetyl-8a-hydroxy-3-isopropenyl-10a-methyldodecahydro-1(2H)-phenanthrenone
  参考文献：
  名称：

  Domino Mukaiyama–Michael reactions in the synthesis of polycyclic systems

  摘要：

  Good results were obtained in the Mukaiyama-Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl6 as catalyst. A second Mukaiyama-Michael reaction of this new silyl enol ether with methyl vinyl ketone and cyclization of the resulting adduct leads to tricyclic compounds in one-pot domino sequences. The scope and limitations of this domino reaction have been investigated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.059

文献信息

• Domino Mukaiyama–Michael reactions in the synthesis of polycyclic systems
  作者：Florence C.E. Sarabèr、Svetlana Dratch、Geke Bosselaar、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/j.tet.2005.11.059

  日期：2006.2

  Good results were obtained in the Mukaiyama-Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl6 as catalyst. A second Mukaiyama-Michael reaction of this new silyl enol ether with methyl vinyl ketone and cyclization of the resulting adduct leads to tricyclic compounds in one-pot domino sequences. The scope and limitations of this domino reaction have been investigated. (c) 2005 Elsevier Ltd. All rights reserved.