3-(2-Ethenyl-4,6-dimethylcyclohexyl)-4-hydroxy-2(1H)-pyridinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(2-Ethenyl-4,6-dimethylcyclohexyl)-4-hydroxy-2(1H)-pyridinone
• 英文别名: 3-(2-ethenyl-4,6-dimethylcyclohexyl)-4-hydroxy-1H-pyridin-2-one
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: SWIJWROLKBJDFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-Ethenyl-4,6-dimethylcyclohexyl)-4-hydroxy-2(1H)-pyridinone 在 三甲基氯硅烷 、 韦德伊斯试剂 、 ethylene diamine tetraacetic acid tetrasodium salt 作用下， 反应 20.0h， 生成 3-[（1S，2R，4S，6R）-2-乙烯基-4,6-二甲基环己基]-1,4-二羟基吡啶-2-酮
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Pyridoxatin

  摘要：

  An efficient two-step route to pyridoxatin analogues 13 and 15 has been developed. Condensation of 4-hydroxypyridone (4) with citronellal (10) affords o-quinone methide intermediate 11, which reacts further to give inverse electron demand Diels-Alder adducts 12 and 16 and ene adduct 14. Oxidation of 12 and 14 with MoO5 by Sammes' procedure completes the synthesis of 13 and 15. Using this approach, the first total synthesis of(+/-)-pyridoxatin (1) has been carried out in seven steps from cis-2,4-dimethylcyclohexanone (21). The key step is the condensation of 4-hydroxypyridone (4) with the allylic silane aldehyde 26 to give 35% of cyclohexylpyridones 2 and 30.

  DOI：

  10.1021/jo00105a024

文献信息

• Total Synthesis of (.+-.)-Pyridoxatin
  作者：Barry B. Snider、Qing Lu

  DOI：10.1021/jo00105a024

  日期：1994.12

  An efficient two-step route to pyridoxatin analogues 13 and 15 has been developed. Condensation of 4-hydroxypyridone (4) with citronellal (10) affords o-quinone methide intermediate 11, which reacts further to give inverse electron demand Diels-Alder adducts 12 and 16 and ene adduct 14. Oxidation of 12 and 14 with MoO5 by Sammes' procedure completes the synthesis of 13 and 15. Using this approach, the first total synthesis of(+/-)-pyridoxatin (1) has been carried out in seven steps from cis-2,4-dimethylcyclohexanone (21). The key step is the condensation of 4-hydroxypyridone (4) with the allylic silane aldehyde 26 to give 35% of cyclohexylpyridones 2 and 30.