tert-butyl (2S,6R)-2-methyl-6-(phenylmethoxymethyl)piperidine-1-carboxylate | 207864-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (2S,6R)-2-methyl-6-(phenylmethoxymethyl)piperidine-1-carboxylate
• CAS: 207864-61-7
• 化学式: C₁₉H₂₉NO₃
• 分子量: 319.444
• InChiKey: RJXYVOOCTRUBMD-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,6R)-2-methyl-6-(phenylmethoxymethyl)piperidine-1-carboxylate 在 palladium on activated charcoal 、 四丙基高钌酸铵 molecular sieve 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate
  参考文献：
  名称：

  Studies Directed Towards the Total Synthesis of (+)-Himbacine

  摘要：

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.

  DOI：

  10.1055/s-1998-5928
• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 在 哌啶 、 lithium aluminium tetrahydride 、 Zn(N3)2-2 pyr 、 偶氮二甲酸二异丙酯 、 lithium tetrachlorocuprate 、 三甲基铝 、 magnesium 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 邻二氯苯 、 甲苯 为溶剂， 反应 6.5h， 生成 tert-butyl (2S,6R)-2-methyl-6-(phenylmethoxymethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Studies Directed Towards the Total Synthesis of (+)-Himbacine

  摘要：

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.

  DOI：

  10.1055/s-1998-5928