(2E,4E)-3-ethoxycarbonyl-6-hydroxy-N-(p-toluenesulfonyl)-2,4-hexadienamide | 1357181-77-1

• 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: (2E,4E)-3-ethoxycarbonyl-6-hydroxy-N-(p-toluenesulfonyl)-2,4-hexadienamide
• 英文别名: ethyl (E,2E)-5-hydroxy-2-[2-[(4-methylphenyl)sulfonylamino]-2-oxoethylidene]pent-3-enoate
• CAS: 1357181-77-1
• 化学式: C₁₆H₁₉NO₆S
• 分子量: 353.396
• InChiKey: SEFYFRSPBIROQE-FPHDLJRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,4E)-3-ethoxycarbonyl-6-hydroxy-N-(p-toluenesulfonyl)-2,4-hexadienamide 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以58%的产率得到ethyl 1-(4-methylphenyl)sulfonyl-5-oxo-2-(2-oxoethyl)-2H-pyrrole-3-carboxylate
  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
• 作为产物：
  描述：

  (Z)-4-ethoxy-3-iodo-4-oxobut-2-enoic acid 在 N-甲基吗啉 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 mineral oil 为溶剂， 反应 3.59h， 生成 (2E,4E)-3-ethoxycarbonyl-6-hydroxy-N-(p-toluenesulfonyl)-2,4-hexadienamide
  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

• 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.