(S)-2,3,4,5-tetrahydro-1H-[2,3']bipyridyl-6-one | 91842-86-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (S)-2,3,4,5-tetrahydro-1H-[2,3']bipyridyl-6-one
• 英文别名: (S)-2,3,4,5-Tetrahydro-1H-[2,3']bipyridyl-6-on；(6S)-6-pyridin-3-ylpiperidin-2-one
• CAS: 91842-86-3
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: ZQAZEUHZHQFEIE-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2,3,4,5-tetrahydro-1H-[2,3']bipyridyl-6-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 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 (5S)-5-[[(1R)-1-naphthalen-1-ylethyl]amino]-5-pyridin-3-ylpentanoate 在 甲酸 、 palladium on carbon 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (S)-2,3,4,5-tetrahydro-1H-[2,3']bipyridyl-6-one
  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

• Menschikoff et al., Chemische Berichte, 1934, vol. 67, p. 1157
  作者：Menschikoff et al.

  DOI：——

  日期：——
• Gol'dfarb et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1962, p. 2209,2211, 2215; engl. Ausg. S. 2112, 2113, 2116
  作者：Gol'dfarb et al.

  DOI：——

  日期：——
• 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.