(2R,3R)-3-benzylamino-2-methoxy-5-nitropentanoic acid methyl ester | 1046161-16-3

• 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: (2R,3R)-3-benzylamino-2-methoxy-5-nitropentanoic acid methyl ester
• 英文别名: methyl (2R,3R)-3-(benzylamino)-2-methoxy-5-nitropentanoate
• CAS: 1046161-16-3
• 化学式: C₁₄H₂₀N₂O₅
• 分子量: 296.323
• InChiKey: NVQVLCSASDTXNB-CHWSQXEVSA-N

物化性质

• 沸点：
  440.2±45.0 °C(predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-benzylamino-2-methoxy-5-nitropentanoic acid methyl ester 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以55%的产率得到(3R,4R)-4-苄基氨基-3-甲氧基哌啶-2-酮
  参考文献：
  名称：

  Synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an important intermediate for (3S,4R)-Cisapride

  摘要：

  An efficient synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an useful intermediate for the chiral synthesis of important drug molecule Cisapride and its analogs, from enantiopure 4-formylazetidin-2-one is described. Synthesis of trans as well as cis isomers of 4-amino-3-methoxypiperidine from 4-formylazetidin-2-one is also achieved in good yield. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.090
• 作为产物：
  描述：

  甲醇 、 (3R,4R)-1-benzyl-3-methoxy-4-(2-nitro-ethyl)-azetidin-2-one 在 盐酸 作用下， 反应 12.0h， 以98%的产率得到(2R,3R)-3-benzylamino-2-methoxy-5-nitropentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an important intermediate for (3S,4R)-Cisapride

  摘要：

  An efficient synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an useful intermediate for the chiral synthesis of important drug molecule Cisapride and its analogs, from enantiopure 4-formylazetidin-2-one is described. Synthesis of trans as well as cis isomers of 4-amino-3-methoxypiperidine from 4-formylazetidin-2-one is also achieved in good yield. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.090

文献信息

• Synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an important intermediate for (3S,4R)-Cisapride
  作者：Nilesh M. Shirode、Anjali P. Likhite、Vikas K. Gumaste、Abdul Rakeeb A.S. Deshmukh

  DOI：10.1016/j.tet.2008.05.090

  日期：2008.7

  An efficient synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an useful intermediate for the chiral synthesis of important drug molecule Cisapride and its analogs, from enantiopure 4-formylazetidin-2-one is described. Synthesis of trans as well as cis isomers of 4-amino-3-methoxypiperidine from 4-formylazetidin-2-one is also achieved in good yield. (c) 2008 Elsevier Ltd. All rights reserved.