2,2-dimethyl-5-(phenylsulfonyl)-4-piperidone | 132644-75-8

• 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-dimethyl-5-(phenylsulfonyl)-4-piperidone
• 英文别名: 2,2-Dimethyl-5-(phenylsulfonyl)-4-piperidinone；5-(benzenesulfonyl)-2,2-dimethylpiperidin-4-one
• CAS: 132644-75-8
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: YECDFSFKDABHAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(phenylsulfonyl)-4-piperidone 以20%的产率得到
  参考文献：
  名称：

  NORMAN, BRYAN H.;GAREAU, YVES;PADWA, ALBERT, J. ORG. CHEM., 56,(1991) N, C. 2154-2161

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-dimethyl-4,5-endo-bis(phenylsulfonyl)-7-oxa-1-azabicyclo<2.2.1>heptane 在 甲醇 、 镍 作用下， 反应 0.33h， 以99%的产率得到2,2-dimethyl-5-(phenylsulfonyl)-4-piperidone
  参考文献：
  名称：

  Tandem addition-cycloaddition reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene as a method for 4-piperidone synthesis

  摘要：

  The reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene affords 7-oxa-1-azanorbornanes in high yield. The formation of the bicyclic isoxazolidine involves conjugate addition of the oxime onto the diene to give a transient nitrone that then undergoes a subsequent intramolecular dipolar cycloaddition reaction. The coupling of several oximes with divinyl sulfone was also studied, and related cycloadducts were obtained in excellent yield. The stereochemistry of the cycloaddition is best explained in terms of an exclusive reaction of the Z isomer of the nitrone via an easily attainable endo orientation of the reactive groups. Molecular mechanics calculations have been refined to accurately predict the regiochemistry of the intramolecular cycloaddition. Treatment of these 7-oxa-1-azanorbornanes with Raney nickel in methanol results in reductive nitrogen-oxygen bond cleavage to give substituted 4-piperidones. The bicyclic isoxazolidine derived from cyclohexanone oxime and bis(phenyl-sulfonyl)diene was converted to the azaspiro[5.5]undecane ring system, which is representative of the key ring skeleton of the perhydrohistrionicotoxin family of alkaloids.

  DOI：

  10.1021/jo00006a036

文献信息

• NORMAN, BRYAN H.;GAREAU, YVES;PADWA, ALBERT, J. ORG. CHEM., 56,(1991) N, C. 2154-2161
  作者：NORMAN, BRYAN H.、GAREAU, YVES、PADWA, ALBERT

  DOI：——

  日期：——
• Tandem addition-cycloaddition reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene as a method for 4-piperidone synthesis
  作者：Bryan H. Norman、Yves Gareau、Albert Padwa

  DOI：10.1021/jo00006a036

  日期：1991.3

  The reaction of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene affords 7-oxa-1-azanorbornanes in high yield. The formation of the bicyclic isoxazolidine involves conjugate addition of the oxime onto the diene to give a transient nitrone that then undergoes a subsequent intramolecular dipolar cycloaddition reaction. The coupling of several oximes with divinyl sulfone was also studied, and related cycloadducts were obtained in excellent yield. The stereochemistry of the cycloaddition is best explained in terms of an exclusive reaction of the Z isomer of the nitrone via an easily attainable endo orientation of the reactive groups. Molecular mechanics calculations have been refined to accurately predict the regiochemistry of the intramolecular cycloaddition. Treatment of these 7-oxa-1-azanorbornanes with Raney nickel in methanol results in reductive nitrogen-oxygen bond cleavage to give substituted 4-piperidones. The bicyclic isoxazolidine derived from cyclohexanone oxime and bis(phenyl-sulfonyl)diene was converted to the azaspiro[5.5]undecane ring system, which is representative of the key ring skeleton of the perhydrohistrionicotoxin family of alkaloids.