6-(4-chlorophenyl)-4-hydroxy-2-phenyl-1-(toluene-4-sulfinyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester | 1254107-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 6-(4-chlorophenyl)-4-hydroxy-2-phenyl-1-(toluene-4-sulfinyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester
• 英文别名: ethyl (2R,6R)-2-(4-chlorophenyl)-4-hydroxy-1-[(S)-(4-methylphenyl)sulfinyl]-6-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1254107-47-5
• 化学式: C₂₇H₂₆ClNO₄S
• 分子量: 496.027
• InChiKey: BNVNIVTXPXIBHN-HNTKEZORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  86
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(4-chlorophenyl)-4-hydroxy-2-phenyl-1-(toluene-4-sulfinyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以65%的产率得到6-(4-chlorophenyl)-4-hydroxy-2-phenyl-1-(toluene-4-sulfonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Domino Imino-Aldol−Aza-Michael Reaction: One-Pot Diastereo- and Enantioselective Synthesis of Piperidines

  摘要：

  Addition of alpha-arylmethylidene- or alpha-alkylidene-beta-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.

  DOI：

  10.1021/jo101680f
• 作为产物：
  描述：

  (E)-ethyl 2-benzylidene-3-oxobutanoate 、 (S)-N-(p-chlorobenzylidene)-p-toluenesulfinamide 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以62%的产率得到6-(4-chlorophenyl)-4-hydroxy-2-phenyl-1-(toluene-4-sulfinyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Domino Imino-Aldol−Aza-Michael Reaction: One-Pot Diastereo- and Enantioselective Synthesis of Piperidines

  摘要：

  Addition of alpha-arylmethylidene- or alpha-alkylidene-beta-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.

  DOI：

  10.1021/jo101680f