Phenylmethyl N-[(3S)-1-(phenylmethyl)-3-piperidinyl]carbamate | 1217476-25-9

• 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: Phenylmethyl N-[(3S)-1-(phenylmethyl)-3-piperidinyl]carbamate
• 英文别名: benzyl N-[(3S)-1-benzylpiperidin-3-yl]carbamate
• CAS: 1217476-25-9
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: KMIYYGARLIZKPI-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 (S)-(-)-[(5,6),(5',6')-双(乙烯二氧)联苯-2,2'-基]二苯基磷 作用下， 以 四氢呋喃 为溶剂， 50.0 ℃ 、2.0 MPa 条件下， 反应 40.0h， 以80%的产率得到
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Hydrogenation of N-(1-benzylpiperidin-3-yl)-enamides: An Efficient Access to Valuable Enantioenriched 3-Aminopiperidine Derivatives

  摘要：

  An efficient synthetic entry to enantioenriched 3-aminopiperidine derivatives using rhodium-catalyzed asymmetric hydrogenation of N-(1-benzylpiperidin-3-yl)enamides is described. This method provides an atom-economical and attractive route to both enantiomers of the valuable 3-aminopiperidine moiety, which is an important structural unit that can be found in many natural products and pharmaceutical drugs encompassing a broad range of biological activities. Under optimized reaction conditions, the targeted 3-aminopiperidine derivatives were obtained in high yields up to 92% and with enantiomeric excesses up to 96% after a single crystallization.

  DOI：

  10.1055/s-0035-1562235

文献信息

• Rhodium-Catalyzed Asymmetric Hydrogenation of N-(1-benzylpiperidin-3-yl)-enamides: An Efficient Access to Valuable Enantioenriched 3-Aminopiperidine Derivatives
  作者：Bernard Boudet、Virginie Ratovelomanana-Vidal、Titouan Royal、Yohan Dudognon、Farouk Berhal、Yvon Bastard、Tahar Ayad

  DOI：10.1055/s-0035-1562235

  日期：——

  An efficient synthetic entry to enantioenriched 3-aminopiperidine derivatives using rhodium-catalyzed asymmetric hydrogenation of N-(1-benzylpiperidin-3-yl)enamides is described. This method provides an atom-economical and attractive route to both enantiomers of the valuable 3-aminopiperidine moiety, which is an important structural unit that can be found in many natural products and pharmaceutical drugs encompassing a broad range of biological activities. Under optimized reaction conditions, the targeted 3-aminopiperidine derivatives were obtained in high yields up to 92% and with enantiomeric excesses up to 96% after a single crystallization.