N-allyl-N-(3-(tert-butyldimethylsilyloxy)propyl)ethenesulfonamide | 1039744-34-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-allyl-N-(3-(tert-butyldimethylsilyloxy)propyl)ethenesulfonamide
• CAS: 1039744-34-7
• 化学式: C₁₄H₂₉NO₃SSi
• 分子量: 319.541
• InChiKey: AYMGIJAYKGTIKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(3-(tert-butyldimethylsilyloxy)propyl)ethenesulfonamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-allyl-6,1,2-oxathiazepine-1,1-dioxide
  参考文献：
  名称：

  Synthesis of Sultam Scaffolds via Intramolecular Oxa-Michael and Diastereoselective Baylis−Hillman Reactions

  摘要：

  A divergent synthetic approach to new sultams utilizing intramolecular oxa-Michael and Baylis-Hillman reactions of readily prepared vinyl sulfonamides and suitably protected amino alcohols, is reported. A variety of seven- and eight-membered ring sultam scaffolds were synthesized using oxa-Michael pathways, whereas both five- and six-membered rings were synthesized using Baylis-Hillman methods. Baylis-Hillman reactions proceed with good to excellent levels of diastereoselectivity, and oxa-Michael reactions leading to eight-membered ring sultams provide empirical evidence validating 8-endo-trig cyclization pathways.

  DOI：

  10.1021/ol8009072
• 作为产物：
  描述：

  、 3-溴丙烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 N-allyl-N-(3-(tert-butyldimethylsilyloxy)propyl)ethenesulfonamide
  参考文献：
  名称：

  Synthesis of Sultam Scaffolds via Intramolecular Oxa-Michael and Diastereoselective Baylis−Hillman Reactions

  摘要：

  A divergent synthetic approach to new sultams utilizing intramolecular oxa-Michael and Baylis-Hillman reactions of readily prepared vinyl sulfonamides and suitably protected amino alcohols, is reported. A variety of seven- and eight-membered ring sultam scaffolds were synthesized using oxa-Michael pathways, whereas both five- and six-membered rings were synthesized using Baylis-Hillman methods. Baylis-Hillman reactions proceed with good to excellent levels of diastereoselectivity, and oxa-Michael reactions leading to eight-membered ring sultams provide empirical evidence validating 8-endo-trig cyclization pathways.

  DOI：

  10.1021/ol8009072