2-(2,2-Dicyano-1-phenylethyl)cyclopentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2,2-Dicyano-1-phenylethyl)cyclopentanone
• 英文别名: 2-[(2-Oxocyclopentyl)-phenylmethyl]propanedinitrile
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: CPORDELNBWCWNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄烯丙二腈 、 1-(三甲基硅氧基)环戊烯 在 lithium perchlorate 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以85%的产率得到2-(2,2-Dicyano-1-phenylethyl)cyclopentanone
  参考文献：
  名称：

  Chemoselectivity in the Michael Addition of Silyl Enol Ethers in Lithium Perchlorate-Diethyl Ether Medium. Evidence for Facile Silyl Group Transfer to Michael Acceptors

  摘要：

  The silyl enol ethers from cyclohexanone and cyclopentanone underwent efficient 1,4-addition to beta-nitro- and beta,beta-dicyanostyrenes in 5 M lithium perchlorate/diethyl ether (LPDE) at ambient temperature to give the corresponding Michael adducts in good yields and with moderate stereoselectivity. The reaction was found to be highly chemoselective in that alpha,beta-unsaturated carbonyl compounds failed to undergo Michael addition with the silyl enol ethers under identical conditions. The experimental evidence suggests that the mechanism involves transfer of the silyl group from the silyl enol ether to the Michael acceptor. The silyl enol ethers reacted with p-benzoquinone in 5 M LPDE to give benzofuran derivatives in good yields. Reaction with chloranil yielded the corresponding O-alkylated products while with DDQ, the corresponding C-alkylated products were obtained in excellent yields and with high regio- and stereoselectivities.

  DOI：

  10.1021/jo00121a022

文献信息

• Chemoselectivity in the Michael Addition of Silyl Enol Ethers in Lithium Perchlorate-Diethyl Ether Medium. Evidence for Facile Silyl Group Transfer to Michael Acceptors
  作者：V. Geetha Saraswathy、S. Sankararaman

  DOI：10.1021/jo00121a022

  日期：1995.8

  The silyl enol ethers from cyclohexanone and cyclopentanone underwent efficient 1,4-addition to beta-nitro- and beta,beta-dicyanostyrenes in 5 M lithium perchlorate/diethyl ether (LPDE) at ambient temperature to give the corresponding Michael adducts in good yields and with moderate stereoselectivity. The reaction was found to be highly chemoselective in that alpha,beta-unsaturated carbonyl compounds failed to undergo Michael addition with the silyl enol ethers under identical conditions. The experimental evidence suggests that the mechanism involves transfer of the silyl group from the silyl enol ether to the Michael acceptor. The silyl enol ethers reacted with p-benzoquinone in 5 M LPDE to give benzofuran derivatives in good yields. Reaction with chloranil yielded the corresponding O-alkylated products while with DDQ, the corresponding C-alkylated products were obtained in excellent yields and with high regio- and stereoselectivities.
• Ramkumar, D.; Sankararaman, S., Journal of the Chemical Society. Perkin transactions II, 1996, # 5, p. 939 - 942
  作者：Ramkumar, D.、Sankararaman, S.

  DOI：——

  日期：——