3-(cyclopent-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-one | 694526-61-9

• 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-(cyclopent-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-one
• 英文别名: 3-(Cyclopenten-1-yl)-1-(4-methylphenyl)sulfonylpiperidin-4-one
• CAS: 694526-61-9
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: HKZCBGGQGVJEEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(cyclopent-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(3RS,4SR)-3-(cyclopent-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-ol
  参考文献：
  名称：

  Synthesis of 3-Substituted 4-Piperidinones via a One-Pot Tandem Oxidation−Cyclization−Oxidation Process:  Stereodivergent Reduction to 3,4-Disubstituted Piperidines

  摘要：

  A novel approach to 3-substituted 4-piperidinones is described. The one-pot tandem oxidation - cyclization - oxidation of unsaturated alcohols 1a-e by PCC or PCC and trifluoromethanesulfonic acid affords piperidinones 2a-e in good yield. Reduction of 2a-e by L-Selectride gives the corresponding cis 3,4-disubstituted piperidines with diastereomeric ratios of >99:1. By contrast, reduction of 2a-e by Al-isopropoxydiisobutylalane gives the trans products with diastereomeric ratios of up to 99:1.

  DOI：

  10.1021/jo0357418
• 作为产物：
  描述：

  N-(3-hydroxypropyl)-4-methyl-N-(2-cyclopentylidene-ethyl)benzenesulfonamide 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以62%的产率得到3-(cyclopent-1-enyl)-1-(toluene-4-sulfonyl)piperidin-4-one
  参考文献：
  名称：

  Synthesis of 3-Substituted 4-Piperidinones via a One-Pot Tandem Oxidation−Cyclization−Oxidation Process:  Stereodivergent Reduction to 3,4-Disubstituted Piperidines

  摘要：

  A novel approach to 3-substituted 4-piperidinones is described. The one-pot tandem oxidation - cyclization - oxidation of unsaturated alcohols 1a-e by PCC or PCC and trifluoromethanesulfonic acid affords piperidinones 2a-e in good yield. Reduction of 2a-e by L-Selectride gives the corresponding cis 3,4-disubstituted piperidines with diastereomeric ratios of >99:1. By contrast, reduction of 2a-e by Al-isopropoxydiisobutylalane gives the trans products with diastereomeric ratios of up to 99:1.

  DOI：

  10.1021/jo0357418

文献信息

• Synthesis of 3-Substituted 4-Piperidinones via a One-Pot Tandem Oxidation−Cyclization−Oxidation Process:  Stereodivergent Reduction to 3,4-Disubstituted Piperidines
  作者：Perdip S. Bahia、John S. Snaith

  DOI：10.1021/jo0357418

  日期：2004.4.1

  A novel approach to 3-substituted 4-piperidinones is described. The one-pot tandem oxidation - cyclization - oxidation of unsaturated alcohols 1a-e by PCC or PCC and trifluoromethanesulfonic acid affords piperidinones 2a-e in good yield. Reduction of 2a-e by L-Selectride gives the corresponding cis 3,4-disubstituted piperidines with diastereomeric ratios of >99:1. By contrast, reduction of 2a-e by Al-isopropoxydiisobutylalane gives the trans products with diastereomeric ratios of up to 99:1.