2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-2-cyclopenten-1-yl)cyclohexanone

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-2-cyclopenten-1-yl)cyclohexanone
• 化学式: C₁₈H₃₂O₂Si
• 分子量: 308.536
• InChiKey: FUNJIQMBIISMQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-2-cyclopenten-1-yl)cyclohexanone 、 丁烯酮 在 triphenylmethylium hexachloroantimonate(V) 作用下， 以 二氯甲烷 为溶剂， 生成 5-acetyl-5a-hydroxy-3a-methyldodecahydro-3H-cyclopenta[a]naphthalen-3-one 、 5-acetyl-5a-hydroxy-3a-methyldodecahydro-3H-cyclopenta[a]naphthalen-3-one
  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
• 作为产物：
  描述：

  甲基环戊烯醇酮 、 tert-butyl(cyclohex-1-en-1-yloxy)dimethylsilane 在 triphenylmethylium hexachloroantimonate(V) 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-2-cyclopenten-1-yl)cyclohexanone
  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.