1-phenyl-2-<(1α,2β,3β)-2-(1-oxoethyl)-3-(2-oxopropyl)cyclopent-1-yl>ethanone | 138879-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2-<(1α,2β,3β)-2-(1-oxoethyl)-3-(2-oxopropyl)cyclopent-1-yl>ethanone
• 英文别名: 1-[(1S,2R,3S)-2-acetyl-3-phenacylcyclopentyl]propan-2-one
• CAS: 138879-12-6
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: GVIJWECGMBLQGN-XYJFISCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-<(1α,2β,3β)-2-(1-oxoethyl)-3-(2-oxopropyl)cyclopent-1-yl>ethanone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以83%的产率得到(1α,3aβ,7aβ)-1-(2-oxo-2-phenylethyl)-5-methyl-2,3,3a,4-tetrahydro-1H-7(7aH)-indenone
  参考文献：
  名称：

  Silyl group-transfer-mediated serial Michael additions

  摘要：

  Three protocols have been developed for achieving ordered, multiple (serial) Michael reactions initiated by silyl enol ethers or silyl ketene acetals. Anion (fluoride or m-chlorobenzoate) catalysis was most effective for reactions of silyl ketene acetal 2 with bis diesters, as in the highly selective formation of 3. Lewis acid (ZnI2) catalysis was more general than anion catalysis and afforded stereochemically complementary products with lower selectivity. The use of SnCl2-trityl chloride was effective in reactions of both silyl ketene acetals and silyl enol ethers with bis enones. Very high stereoselectivity was generally observed in the formation of cyclopentanes. The products of serial Michael reactions of bis enones could be regiospecifically cyclized to bicyclic enones. Overall, it was found that the serial Michael reactions initiated by silyl enolates can be used to form efficiently and selectively complex cyclics from simple acyclic precursors.

  DOI：

  10.1021/jo00032a026
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 (3E,7E)-deca-3,7-diene-2,9-dione 在 三苯基氯甲烷 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以80%的产率得到1-phenyl-2-<(1α,2β,3β)-2-(1-oxoethyl)-3-(2-oxopropyl)cyclopent-1-yl>ethanone
  参考文献：
  名称：

  Silyl group-transfer-mediated serial Michael additions

  摘要：

  Three protocols have been developed for achieving ordered, multiple (serial) Michael reactions initiated by silyl enol ethers or silyl ketene acetals. Anion (fluoride or m-chlorobenzoate) catalysis was most effective for reactions of silyl ketene acetal 2 with bis diesters, as in the highly selective formation of 3. Lewis acid (ZnI2) catalysis was more general than anion catalysis and afforded stereochemically complementary products with lower selectivity. The use of SnCl2-trityl chloride was effective in reactions of both silyl ketene acetals and silyl enol ethers with bis enones. Very high stereoselectivity was generally observed in the formation of cyclopentanes. The products of serial Michael reactions of bis enones could be regiospecifically cyclized to bicyclic enones. Overall, it was found that the serial Michael reactions initiated by silyl enolates can be used to form efficiently and selectively complex cyclics from simple acyclic precursors.

  DOI：

  10.1021/jo00032a026

文献信息

• Silyl group-transfer-mediated serial Michael additions
  作者：Peter G. Klimko、Daniel A. Singleton

  DOI：10.1021/jo00032a026

  日期：1992.3

  Three protocols have been developed for achieving ordered, multiple (serial) Michael reactions initiated by silyl enol ethers or silyl ketene acetals. Anion (fluoride or m-chlorobenzoate) catalysis was most effective for reactions of silyl ketene acetal 2 with bis diesters, as in the highly selective formation of 3. Lewis acid (ZnI2) catalysis was more general than anion catalysis and afforded stereochemically complementary products with lower selectivity. The use of SnCl2-trityl chloride was effective in reactions of both silyl ketene acetals and silyl enol ethers with bis enones. Very high stereoselectivity was generally observed in the formation of cyclopentanes. The products of serial Michael reactions of bis enones could be regiospecifically cyclized to bicyclic enones. Overall, it was found that the serial Michael reactions initiated by silyl enolates can be used to form efficiently and selectively complex cyclics from simple acyclic precursors.