(2E,4E)-3-((tert-butyldiphenylsiloxy)methyl)-6-hydroxy-N-(p-toluenesulfonyl)-2,4-hexadienamide | 1357181-81-7

• 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: (2E,4E)-3-((tert-butyldiphenylsiloxy)methyl)-6-hydroxy-N-(p-toluenesulfonyl)-2,4-hexadienamide
• CAS: 1357181-81-7
• 化学式: C₃₀H₃₅NO₅SSi
• 分子量: 549.763
• InChiKey: OFCAMEPCCURIHS-XMNZYIGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2E,4E)-3-((tert-butyldiphenylsiloxy)methyl)-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27%的产率得到2-(3-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxo-1-tosyl-2,5-dihydro-1H-pyrrol-2-yl)acetaldehyde
  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)-2-iodo-1-(tert-butyldiphenylsiloxy)but-2-en-4-ol 在 N-甲基吗啉 、 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium chlorite 、 copper(l) iodide 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 mineral oil 、 叔丁醇 为溶剂， 反应 6.34h， 生成 (2E,4E)-3-((tert-butyldiphenylsiloxy)methyl)-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