N-[1-(4-fluorophenyl)-2-hydroxymethyl-allyl]-4-methylbenzenesulfonamide | 654653-48-2

• 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: N-[1-(4-fluorophenyl)-2-hydroxymethyl-allyl]-4-methylbenzenesulfonamide
• 英文别名: N-[1-(4-fluorophenyl)-2-(hydroxymethyl)prop-2-enyl]-4-methylbenzenesulfonamide
• CAS: 654653-48-2
• 化学式: C₁₇H₁₈FNO₃S
• 分子量: 335.399
• InChiKey: BCRXSVYNGCLVCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-[1-(4-fluorophenyl)-2-hydroxymethyl-allyl]-4-methylbenzenesulfonamide 在 甲醇 、 4-二甲氨基吡啶 、 magnesium 作用下， 以 二氯甲烷 为溶剂， 反应 2.75h， 生成 tert-butyl [1-(4-fluorophenyl)-2-hydroxymethylallyl]carbamate
  参考文献：
  名称：

  Highly Efficient aza-Baylis−Hillman Reaction of N-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds

  摘要：

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.

  DOI：

  10.1021/jo035103p
• 作为产物：
  描述：

  N-[2-formyl-1-(4-fluorophenyl)allyl]-4-methylbenzenesulfonamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到N-[1-(4-fluorophenyl)-2-hydroxymethyl-allyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Highly Efficient aza-Baylis−Hillman Reaction of N-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds

  摘要：

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.

  DOI：

  10.1021/jo035103p