(3S)-1-allyl-3-benzylamino-6-(1-hydroxy-2,2-dimethylpropyl)piperidin-2-one | 1160861-07-3

• 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: (3S)-1-allyl-3-benzylamino-6-(1-hydroxy-2,2-dimethylpropyl)piperidin-2-one
• 英文别名: (3S)-3-(benzylamino)-6-(1-hydroxy-2,2-dimethylpropyl)-1-prop-2-enylpiperidin-2-one
• CAS: 1160861-07-3
• 化学式: C₂₀H₃₀N₂O₂
• 分子量: 330.47
• InChiKey: SCENJQWKPQPANG-AOCRQIFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S)-1-allyl-3-benzylamino-6-phenylsulfanylpiperidin-2-one 、 特戊醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以34%的产率得到(3S)-1-allyl-3-benzylamino-6-(1-hydroxy-2,2-dimethylpropyl)piperidin-2-one
  参考文献：
  名称：

  Facile Syntheses of Three Ahp-Type Building Blocks with Complementary Reactivity

  摘要：

  Two protected 3-amino-6-hydroxy-2-piperidone derivatives (Ahp, 12 and 6), as well as a thioether analogue (7) were synthesized starting from L-glutamic acid in four, five, and six steps respectively. The Ahp derivatives 12 and 6 are not only the structural feature found in many naturally occurring bioactive depsipeptides, but also precursors of the N-acyliminium such as D; while the (S)-thioether 7 was shown to be an effective synthetic equivalent of the novel 2-piperidone N-alpha-carbanion E via the lithium-naphthalenide (LN)-mediated reductive lithiation, capable of reacting with carbonyl compounds without an acidic alpha-proton to give the alpha-hydroxyalkylation products.

  DOI：

  10.3987/com-08-s(d)35

文献信息

• Facile Syntheses of Three Ahp-Type Building Blocks with Complementary Reactivity
  作者：Pei-Qiang Huang、Wen Chen、Xiao Zheng、Yuan-Ping Ruan

  DOI：10.3987/com-08-s(d)35

  日期：——

  Two protected 3-amino-6-hydroxy-2-piperidone derivatives (Ahp, 12 and 6), as well as a thioether analogue (7) were synthesized starting from L-glutamic acid in four, five, and six steps respectively. The Ahp derivatives 12 and 6 are not only the structural feature found in many naturally occurring bioactive depsipeptides, but also precursors of the N-acyliminium such as D; while the (S)-thioether 7 was shown to be an effective synthetic equivalent of the novel 2-piperidone N-alpha-carbanion E via the lithium-naphthalenide (LN)-mediated reductive lithiation, capable of reacting with carbonyl compounds without an acidic alpha-proton to give the alpha-hydroxyalkylation products.