methyl 1-[(1S)-phenylethyl]-4-(benzyloxycarbonylamino)piperidine-4-carboxylate | 839721-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 1-[(1S)-phenylethyl]-4-(benzyloxycarbonylamino)piperidine-4-carboxylate
• 英文别名: methyl 1-[(1S)-1-phenylethyl]-4-(phenylmethoxycarbonylamino)piperidine-4-carboxylate
• CAS: 839721-96-9
• 化学式: C₂₃H₂₈N₂O₄
• 分子量: 396.486
• InChiKey: KKOOGMCSNKUGOX-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-[(1S)-phenylethyl]-4-(benzyloxycarbonylamino)piperidine-4-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以100%的产率得到1-[(1S)-phenylethyl]-4-(benzyloxycarbonylamino)piperidine-4-carboxylic acid
  参考文献：
  名称：

  Concise synthetic strategy toward cyclic α,α-disubstituted α-amino acids bearing a δ-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids

  摘要：

  A concise synthetic strategy toward cyclic alpha,alpha-disubstituted alpha-amino acids, 1-substituted 4-aminopiperidine-4-carboxylic acids have been developed. The synthetic route is a reductive amination of dimethyl bis(dioxoianemethyl)malonate with various amines, followed by Curtius rearrangement. This synthetic route is capable of synthesizing 4-aminopiperidine-4-carboxylic acids bearing a bulky substituent and optically active ones bearing a pendent chiral substituent, by the change of condensed amines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.004
• 作为产物：
  描述：

  1-[(1S)-phenylethyl]-bis(methoxycarbonyl)-1,4-dihydropyridine 在 palladium on activated charcoal sodium hydroxide 、 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.0h， 生成 methyl 1-[(1S)-phenylethyl]-4-(benzyloxycarbonylamino)piperidine-4-carboxylate
  参考文献：
  名称：

  Concise synthetic strategy toward cyclic α,α-disubstituted α-amino acids bearing a δ-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids

  摘要：

  A concise synthetic strategy toward cyclic alpha,alpha-disubstituted alpha-amino acids, 1-substituted 4-aminopiperidine-4-carboxylic acids have been developed. The synthetic route is a reductive amination of dimethyl bis(dioxoianemethyl)malonate with various amines, followed by Curtius rearrangement. This synthetic route is capable of synthesizing 4-aminopiperidine-4-carboxylic acids bearing a bulky substituent and optically active ones bearing a pendent chiral substituent, by the change of condensed amines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.004

文献信息

• Concise synthetic strategy toward cyclic α,α-disubstituted α-amino acids bearing a δ-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids
  作者：Makoto Oba、Masakazu Tanaka、Yukiko Takano、Hiroshi Suemune

  DOI：10.1016/j.tet.2004.11.004

  日期：2005.1

  A concise synthetic strategy toward cyclic alpha,alpha-disubstituted alpha-amino acids, 1-substituted 4-aminopiperidine-4-carboxylic acids have been developed. The synthetic route is a reductive amination of dimethyl bis(dioxoianemethyl)malonate with various amines, followed by Curtius rearrangement. This synthetic route is capable of synthesizing 4-aminopiperidine-4-carboxylic acids bearing a bulky substituent and optically active ones bearing a pendent chiral substituent, by the change of condensed amines. (C) 2004 Elsevier Ltd. All rights reserved.