3-(Phenylsulfonyl)-5-acetyl-1,2-hepten-6-one | 155187-11-4

• 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: 3-(Phenylsulfonyl)-5-acetyl-1,2-hepten-6-one
• CAS: 155187-11-4
• 化学式: C₁₅H₁₆O₄S
• 分子量: 292.356
• InChiKey: UAZPCQZVERBJEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(Phenylsulfonyl)-5-acetyl-1,2-hepten-6-one 在 sodium benzenesulfonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 3-Acetyl-2,6-dimethyl-5-(phenylsulfonyl)-4H-pyran
  参考文献：
  名称：

  Cyclization Reactions of 2,3-Bis(phenylsulfonyl)-1,3-butadiene with Various Carbanions. A [4 + 1] Anionic Annulation Approach to Phenylsulfonyl-Substituted Cyclopentenes

  摘要：

  2,3-Bis(phenylsulfonyl)-1,3-butadiene undergo es conjugate addition in the presence of carbanions giving rise to a variety of unsaturated sulfones. Reaction with lithium enolates proceeds via an allylic anionic intermediate which undergoes a subsequent elimination of phenylsulfinate anion to produce an allene. Generation of enolates from silyl enol ethers results in conjugate addition to the diene without subsequent elimination. Substituted cyclopentenyl sulfones are available via a [4 + 1] annulation reaction of the diene with various distabilized carbanions. The reaction involves a tandem addition-proton exchange-addition sequence. In the special case of 2,4-pentanedione, pyrans are formed, the isomeric identity of which depends upon the reaction conditions. 2-Alkylated 1,3-dicarbonyl compounds react with the activated diene to produce substituted allenes in high yield. Phenylsulfonyl alkenyl substituted allenes were conveniently prepared by a similar protocol and were found to serve as substrates for intramolecular [2 + 2] cycloaddition chemistry.

  DOI：

  10.1021/jo00082a015
• 作为产物：
  描述：

  2,3-bis(phenylsulfonyl)-1,3-butadiene 、 乙酰丙酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到1-(Phenylsulfonyl)-3,3-diacetyl-1-cyclopentene
  参考文献：
  名称：

  Cyclization Reactions of 2,3-Bis(phenylsulfonyl)-1,3-butadiene with Various Carbanions. A [4 + 1] Anionic Annulation Approach to Phenylsulfonyl-Substituted Cyclopentenes

  摘要：

  2,3-Bis(phenylsulfonyl)-1,3-butadiene undergo es conjugate addition in the presence of carbanions giving rise to a variety of unsaturated sulfones. Reaction with lithium enolates proceeds via an allylic anionic intermediate which undergoes a subsequent elimination of phenylsulfinate anion to produce an allene. Generation of enolates from silyl enol ethers results in conjugate addition to the diene without subsequent elimination. Substituted cyclopentenyl sulfones are available via a [4 + 1] annulation reaction of the diene with various distabilized carbanions. The reaction involves a tandem addition-proton exchange-addition sequence. In the special case of 2,4-pentanedione, pyrans are formed, the isomeric identity of which depends upon the reaction conditions. 2-Alkylated 1,3-dicarbonyl compounds react with the activated diene to produce substituted allenes in high yield. Phenylsulfonyl alkenyl substituted allenes were conveniently prepared by a similar protocol and were found to serve as substrates for intramolecular [2 + 2] cycloaddition chemistry.

  DOI：

  10.1021/jo00082a015

文献信息

• Cyclization Reactions of 2,3-Bis(phenylsulfonyl)-1,3-butadiene with Various Carbanions. A [4 + 1] Anionic Annulation Approach to Phenylsulfonyl-Substituted Cyclopentenes
  作者：Albert Padwa、Michelle A. Filipkowski、Michael Meske、S. Shaun Murphree、Scott H. Watterson、Zhijie Ni

  DOI：10.1021/jo00082a015

  日期：1994.2

  2,3-Bis(phenylsulfonyl)-1,3-butadiene undergo es conjugate addition in the presence of carbanions giving rise to a variety of unsaturated sulfones. Reaction with lithium enolates proceeds via an allylic anionic intermediate which undergoes a subsequent elimination of phenylsulfinate anion to produce an allene. Generation of enolates from silyl enol ethers results in conjugate addition to the diene without subsequent elimination. Substituted cyclopentenyl sulfones are available via a [4 + 1] annulation reaction of the diene with various distabilized carbanions. The reaction involves a tandem addition-proton exchange-addition sequence. In the special case of 2,4-pentanedione, pyrans are formed, the isomeric identity of which depends upon the reaction conditions. 2-Alkylated 1,3-dicarbonyl compounds react with the activated diene to produce substituted allenes in high yield. Phenylsulfonyl alkenyl substituted allenes were conveniently prepared by a similar protocol and were found to serve as substrates for intramolecular [2 + 2] cycloaddition chemistry.