methyl (S,E)-5-((R)-1-(naphthalen-1-yl)ethylamino)-5-cyclohexylpent-2-enoate | 1296689-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl (S,E)-5-((R)-1-(naphthalen-1-yl)ethylamino)-5-cyclohexylpent-2-enoate
• CAS: 1296689-51-4
• 化学式: C₂₄H₃₁NO₂
• 分子量: 365.516
• InChiKey: FFUSVZHICUGYIP-IOLGKOKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (S,E)-5-((R)-1-(naphthalen-1-yl)ethylamino)-5-cyclohexylpent-2-enoate 在 lithium aluminium tetrahydride 、 palladium on carbon 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 (2S)-2-cyclohexylpiperidine
  参考文献：
  名称：

  A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

  摘要：

  A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.090
• 作为产物：
  描述：

  (R)-1-(1-萘基)乙胺 、 1-(trimethylsiloxy)-1-methoxy-1,3-butadiene 、 环己烷基甲醛 在 tin(II) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以71%的产率得到methyl (S,E)-5-((R)-1-(naphthalen-1-yl)ethylamino)-5-cyclohexylpent-2-enoate
  参考文献：
  名称：

  A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

  摘要：

  A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.090