N-[2-formyl-1-(3-chlorophenyl)allyl]-4-methylbenzenesulfonamide | 654653-35-7

• 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-[2-formyl-1-(3-chlorophenyl)allyl]-4-methylbenzenesulfonamide
• 英文别名: 2-methylene-3-(3-chlorophenyl)-3-(p-tosylamino)propanaldehyde；N-[1-(3-chlorophenyl)-2-formylprop-2-enyl]-4-methylbenzenesulfonamide
• CAS: 654653-35-7
• 化学式: C₁₇H₁₆ClNO₃S
• 分子量: 349.838
• InChiKey: HOYRHGCDYGAOFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  丙烯醛 、 N-[2-formyl-1-(3-chlorophenyl)allyl]-4-methylbenzenesulfonamide 在 (2'-Hydroxy-1,1'-biphen-2-yl)diphenylphosphane 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以48%的产率得到6-(3-chlorophenyl)-1,2,5,6-tetrahydro-5-methylene-1-tosylpyridine-3-carbaldehyde
  参考文献：
  名称：

  双功能膦有机催化剂催化的新型选择性氮杂-Morita-Baylis-Hillman（氮杂-MBH）多米诺反应和N-磺化亚胺与丙烯醛的氮杂-MBH反应。

  摘要：

  DOI：

  10.1002/chem.200800753
• 作为产物：
  描述：

  丙烯醛 、 (E)-N-(3-chlorobenzylidene)-4-methylbenzenesulfonamide 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以82%的产率得到N-[2-formyl-1-(3-chlorophenyl)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

文献信息

• Highly Efficient aza-Baylis−Hillman Reaction of <i>N</i>-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
  作者：Yong-Mei Xu、Min Shi

  DOI：10.1021/jo035103p

  日期：2004.1.1

  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.
• A Novel Selective Aza-Morita-Baylis-Hillman (aza-MBH) Domino Reaction and Aza-MBH Reaction of N-Sulfonated Imines with Acrolein Catalyzed by a Bifunctional Phosphine Organocatalyst
  作者：Xiangtai Meng、You Huang、Ruyu Chen

  DOI：10.1002/chem.200800753

  日期：2008.8.8