1-[(1S,2R)-2-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1,2-dihydro-naphthalen-1-yl]-piperidine | 157130-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(1S,2R)-2-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1,2-dihydro-naphthalen-1-yl]-piperidine
• 英文别名: (4S)-4-tert-butyl-2-[(1S,2R)-2-methyl-1-piperidin-1-yl-1H-naphthalen-2-yl]-4,5-dihydro-1,3-oxazole
• CAS: 157130-96-6
• 化学式: C₂₃H₃₂N₂O
• 分子量: 352.52
• InChiKey: VTLKWSRGAZHTMT-ZRCGQRJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(1S,2R)-2-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1,2-dihydro-naphthalen-1-yl]-piperidine 在 盐酸 作用下， 反应 16.0h， 以92%的产率得到(1S,2R)-2-Methyl-1-piperidin-1-yl-1,2-dihydro-naphthalene-2-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：

  2-萘甲酸 在 六甲基磷酰三胺 、 正丁基锂 、 氯化亚砜 、 草酰氯 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.08h， 生成 1-[(1S,2R)-2-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1,2-dihydro-naphthalen-1-yl]-piperidine
  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

文献信息

• Shimano, Masanao; Meyers, Journal of the American Chemical Society, 1994, vol. 116, # 14, p. 6437 - 6438
  作者：Shimano, Masanao、Meyers

  DOI：——

  日期：——
• Shimano Masanao, Meyers A. I., J. Amer. Chem. Soc, 116 (1994) N 14, S 6437- 6438
  作者：Shimano Masanao, Meyers A. I.

  DOI：——

  日期：——