methyl (5S)-5-[[(1R)-1-naphthalen-1-ylethyl]amino]-5-pyridin-3-ylpentanoate | 1296689-65-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (5S)-5-[[(1R)-1-naphthalen-1-ylethyl]amino]-5-pyridin-3-ylpentanoate
• CAS: 1296689-65-0
• 化学式: C₂₃H₂₆N₂O₂
• 分子量: 362.472
• InChiKey: CVWFOWRKAMJGPC-VGSWGCGISA-N

物化性质

• 沸点：
  519.4±50.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5S)-5-[[(1R)-1-naphthalen-1-ylethyl]amino]-5-pyridin-3-ylpentanoate 在 lithium aluminium tetrahydride 、 甲酸 、 palladium on carbon 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 新烟碱
  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：

  methyl (E,5S)-5-[[(1R)-1-naphthalen-1-ylethyl]amino]-5-pyridin-3-ylpent-2-enoate 在 palladium on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 methyl (5S)-5-[[(1R)-1-naphthalen-1-ylethyl]amino]-5-pyridin-3-ylpentanoate
  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

文献信息

• A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine
  作者：Yang Yang、Dean P. Phillips、Shifeng Pan

  DOI：10.1016/j.tetlet.2011.01.090

  日期：2011.4

  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.