1-[(1R,2R,3R,5S)-isopinocampheyl]-bis(methoxycarbonyl)-1,4-dihydropyridine | 839721-86-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[(1R,2R,3R,5S)-isopinocampheyl]-bis(methoxycarbonyl)-1,4-dihydropyridine
• 英文别名: dimethyl 1-[(1R,2R,3R,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridine-4,4-dicarboxylate
• CAS: 839721-86-7
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: WCQQMYWQIZNIQS-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[(1R,2R,3R,5S)-isopinocampheyl]-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， 生成 methyl 1-[(1R,2R,3R,5S)-isopinocampheyl]-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
• 作为产物：
  描述：

  dimethyl 2,2-bis((1,3-dioxolan-2-yl)methyl)malonate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-[(1R,2R,3R,5S)-isopinocampheyl]-bis(methoxycarbonyl)-1,4-dihydropyridine
  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