1-[(1S,2R)-2-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1,2-dihydro-naphthalen-1-yl]-piperidin-4-one | 172329-34-9

• 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]-piperidin-4-one
• 英文别名: 1-[(1S,2R)-2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]-2-methyl-1H-naphthalen-1-yl]piperidin-4-one
• CAS: 172329-34-9
• 化学式: C₂₃H₃₀N₂O₂
• 分子量: 366.503
• InChiKey: HYJPMZGTDGWFNK-ZRCGQRJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

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]-piperidin-4-one 在 sodium hydroxide 、 正丁胺 作用下， 反应 20.0h， 以72%的产率得到(1S,2R)-1-Amino-2-methyl-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-(2'-Naphthyl)-4-(S)-tert-butyloxazoline 在 盐酸 、 六甲基磷酰三胺 、 正丁基锂 作用下， 反应 5.41h， 生成 1-[(1S,2R)-2-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-2-methyl-1,2-dihydro-naphthalen-1-yl]-piperidin-4-one
  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

• Asymmetric Diastereoselective Conjugate Additions of Lithium Amides to Chiral Naphthyloxazolines Leading to Novel .beta.-Amino Acids
  作者：Masanao Shimano、A. I. Meyers

  DOI：10.1021/jo00128a016

  日期：1995.11

  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.