(1R,2S)-1-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2-dihydro-naphthalen-2-ylamine | 157130-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-1-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2-dihydro-naphthalen-2-ylamine
• 英文别名: (1R,2S)-1-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]-1-methyl-2H-naphthalen-2-amine
• CAS: 157130-99-9
• 化学式: C₁₈H₂₄N₂O
• 分子量: 284.401
• InChiKey: SOCNDTBVRNBXSC-HDMKZQKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2-dihydro-naphthalen-2-ylamine 在 盐酸 作用下， 以85%的产率得到(1R,2S)-2-氨基-1-甲基-1,2-二氢-1-萘甲酸
  参考文献：
  名称：

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

  摘要：

  DOI：
• 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 、 正丁胺 作用下， 反应 17.41h， 生成 (1R,2S)-1-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2-dihydro-naphthalen-2-ylamine
  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：——
• 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.