4-ethoxycarbonyl-6-(2-naphthyl)-1-(p-toluenesulfonyl)-1,6-dihydropyridin-2(3H)-one | 1357181-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-ethoxycarbonyl-6-(2-naphthyl)-1-(p-toluenesulfonyl)-1,6-dihydropyridin-2(3H)-one
• 英文别名: Ethyl 1-(4-methylphenyl)sulfonyl-2-naphthalen-2-yl-6-oxo-2,5-dihydropyridine-4-carboxylate；ethyl 1-(4-methylphenyl)sulfonyl-2-naphthalen-2-yl-6-oxo-2,5-dihydropyridine-4-carboxylate
• CAS: 1357181-54-4
• 化学式: C₂₅H₂₃NO₅S
• 分子量: 449.527
• InChiKey: ZOVHBDBFFAWULO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲苯磺酰胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 邻二甲苯 、 mineral oil 为溶剂， 反应 6.17h， 生成 4-ethoxycarbonyl-6-(2-naphthyl)-1-(p-toluenesulfonyl)-1,6-dihydropyridin-2(3H)-one
  参考文献：
  名称：

  New type of azacyclization: thermal preparation of 4,6-disubstituted 2-piperidinone from N-sulfonyldienamide and its substituent effect

  摘要：

  The thermal 6-endo cyclization of N-sulfonyl-2,4-dienamide compounds to produce 4,6-disubstituted 2-piperidinone is described. The observed remarkable substituent effect due to the N-sulfonyl and C3 ethoxycarbonyl groups for acceleration of this 6-endo cyclization strongly suggests that the reaction would proceed via the 6 pi-azaelectrocyclization of the intermediary imidic acid. On the contrary, the corresponding 5-formyl and 5-acetyl derivatives rapidly cyclized at room temperature to produce the 5-exo cyclized products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.014

文献信息

• Palladium-Catalyzed Asymmetric 6-Endo Cyclization of Dienamides with Substituent-Driven Activation
  作者：Hiroshi Tsuchikawa、Yuya Maekawa、Shigeo Katsumura

  DOI：10.1021/ol300737t

  日期：2012.5.4

  Chiral 2-piperidinone compounds with various C-6 substituents were successfully synthesized via a Pd-catalyzed asymmetric 6-endo cyclization of dienamides, which were evidently activated by both N-p-toluenesulfonyl and C-3 ester substituents.
• New type of azacyclization: thermal preparation of 4,6-disubstituted 2-piperidinone from N-sulfonyldienamide and its substituent effect
  作者：Yuya Maekawa、Taku Sakaguchi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1016/j.tetlet.2011.12.014

  日期：2012.2

  The thermal 6-endo cyclization of N-sulfonyl-2,4-dienamide compounds to produce 4,6-disubstituted 2-piperidinone is described. The observed remarkable substituent effect due to the N-sulfonyl and C3 ethoxycarbonyl groups for acceleration of this 6-endo cyclization strongly suggests that the reaction would proceed via the 6 pi-azaelectrocyclization of the intermediary imidic acid. On the contrary, the corresponding 5-formyl and 5-acetyl derivatives rapidly cyclized at room temperature to produce the 5-exo cyclized products. (C) 2011 Elsevier Ltd. All rights reserved.