(2R,3S,4S,5R)-3-benzyl-2-hydroxy-5-nitro-4-propylpiperidine-1-carboxylic acid benzyl ester | 1273558-90-9

• 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: (2R,3S,4S,5R)-3-benzyl-2-hydroxy-5-nitro-4-propylpiperidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2R,3S,4S,5R)-3-benzyl-2-hydroxy-5-nitro-4-propylpiperidine-1-carboxylate
• CAS: 1273558-90-9
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: WWBOWYDVVXGMLK-MYGLTJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-3-benzyl-2-hydroxy-5-nitro-4-propylpiperidine-1-carboxylic acid benzyl ester 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4S,5R)-3-benzyl-5-nitro-4-propylpiperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Organocatalytic Approach to Polysubstituted Piperidines and Tetrahydropyrans

  摘要：

  Polysubstituted piperidines and tetrahydropyrans are synthesized from aldehydes and two classes of trisubstituted nitroolefins via an O-TMS protected diphenylprolinol catalyzed domino Michael addition/aminalization (or acetalization) process. This approach allows formation of four contiguous stereocenters in the piperidine or tetrahydropyran ring in one step with excellent enantioselectivity.

  DOI：

  10.1021/ol200004s
• 作为产物：
  描述：

  (2-nitroethyl)carbamic acid benzyl ester 在 (2R)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 potassium tert-butylate 、 苯甲酸 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 6.5h， 生成 (2R,3S,4S,5R)-3-benzyl-2-hydroxy-5-nitro-4-propylpiperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Organocatalytic Approach to Polysubstituted Piperidines and Tetrahydropyrans

  摘要：

  Polysubstituted piperidines and tetrahydropyrans are synthesized from aldehydes and two classes of trisubstituted nitroolefins via an O-TMS protected diphenylprolinol catalyzed domino Michael addition/aminalization (or acetalization) process. This approach allows formation of four contiguous stereocenters in the piperidine or tetrahydropyran ring in one step with excellent enantioselectivity.

  DOI：

  10.1021/ol200004s

文献信息

• Organocatalytic Approach to Polysubstituted Piperidines and Tetrahydropyrans
  作者：You Wang、Shaolin Zhu、Dawei Ma

  DOI：10.1021/ol200004s

  日期：2011.4.1

  Polysubstituted piperidines and tetrahydropyrans are synthesized from aldehydes and two classes of trisubstituted nitroolefins via an O-TMS protected diphenylprolinol catalyzed domino Michael addition/aminalization (or acetalization) process. This approach allows formation of four contiguous stereocenters in the piperidine or tetrahydropyran ring in one step with excellent enantioselectivity.