(1R,2S)-2-氨基-1-甲基-1,2-二氢-1-萘甲酸 | 157131-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (1R,2S)-2-氨基-1-甲基-1,2-二氢-1-萘甲酸
• 英文名称: (1R,2S)-2-Amino-1-methyl-1,2-dihydro-naphthalene-1-carboxylic acid
• 英文别名: 1-Naphthalenecarboxylicacid, 2-amino-1,2-dihydro-1-methyl-, (1R,2S)-；(1R,2S)-2-amino-1-methyl-2H-naphthalene-1-carboxylic acid
• CAS: 157131-00-5
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: XCBLFMYHCGCXEL-CMPLNLGQSA-N

物化性质

• 沸点：
  373.8±42.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(1R,2S)-1-((S)-4-tert-Butyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2-dihydro-naphthalen-2-ylamine	157130-99-9	C18H24N2O	284.401

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-氨基-1-甲基-1,2-二氢-1-萘甲酸 在 碳酸氢钠 、 甲基磺酰氯 作用下， 以 异丙醇 为溶剂， 反应 58.0h， 以74%的产率得到(2aS,8bR)-8b-Methyl-2a,8b-dihydro-2H-naphtho[2,1-b]azet-1-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
• 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 23.41h， 生成 (1R,2S)-2-氨基-1-甲基-1,2-二氢-1-萘甲酸
  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.