(1R,2S)-1-Methyl-2-piperidin-1-yl-1,2-dihydro-naphthalene-1-carboxylic acid (S)-2-acetylamino-3,3-dimethyl-butyl ester | 172329-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-1-Methyl-2-piperidin-1-yl-1,2-dihydro-naphthalene-1-carboxylic acid (S)-2-acetylamino-3,3-dimethyl-butyl ester
• 英文别名: [(2S)-2-acetamido-3,3-dimethylbutyl] (1R,2S)-1-methyl-2-piperidin-1-yl-2H-naphthalene-1-carboxylate
• CAS: 172329-37-2
• 化学式: C₂₅H₃₆N₂O₃
• 分子量: 412.572
• InChiKey: ICBFIMZIVMCFAO-OTNCWRBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-Methyl-2-piperidin-1-yl-1,2-dihydro-naphthalene-1-carboxylic acid (S)-2-acetylamino-3,3-dimethyl-butyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以94%的产率得到(1R,2S)-1-Methyl-2-piperidin-1-yl-1,2-dihydro-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Asymmetric Diastereoselective Conjugate Additions of Lithium Amides to Chiral Naphthyloxazolines Leading to Novel .beta.-Amino Acids

  摘要：

  The functionalization of the naphthalene ring system by a direct amination-alkylation reaction of chiral nonracemic naphthyloxazolines is described. Chiral 1-naphthyl- and 2-naphthyloxazoline were treated with a variety of lithium amides followed by several different electrophilic quenches. The solvent and additives were varied in. order to achieve optimum conditions. The combination of HMPA and THF at -78 degrees C gave the best yield with excellent stereoselectivity. The present methodology provides a stereospecific synthesis of novel, nonracemic, rigid beta-amino acids after hydrolytic removal of the chiral oxazoline.

  DOI：

  10.1021/jo00128a016
• 作为产物：
  描述：

  1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene 在 盐酸 、 六甲基磷酰三胺 、 sodium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 7.08h， 生成 (1R,2S)-1-Methyl-2-piperidin-1-yl-1,2-dihydro-naphthalene-1-carboxylic acid (S)-2-acetylamino-3,3-dimethyl-butyl ester
  参考文献：
  名称：

  Asymmetric Diastereoselective Conjugate Additions of Lithium Amides to Chiral Naphthyloxazolines Leading to Novel .beta.-Amino Acids

  摘要：

  The functionalization of the naphthalene ring system by a direct amination-alkylation reaction of chiral nonracemic naphthyloxazolines is described. Chiral 1-naphthyl- and 2-naphthyloxazoline were treated with a variety of lithium amides followed by several different electrophilic quenches. The solvent and additives were varied in. order to achieve optimum conditions. The combination of HMPA and THF at -78 degrees C gave the best yield with excellent stereoselectivity. The present methodology provides a stereospecific synthesis of novel, nonracemic, rigid beta-amino acids after hydrolytic removal of the chiral oxazoline.

  DOI：

  10.1021/jo00128a016