(1S,2R)-1-Acetylamino-2-methyl-1,2-dihydro-naphthalene-2-carboxylic acid | 1025950-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2R)-1-Acetylamino-2-methyl-1,2-dihydro-naphthalene-2-carboxylic acid
• 英文别名: (1S,2R)-1-acetamido-2-methyl-1H-naphthalene-2-carboxylic acid
• CAS: 1025950-49-5
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: OJPCLSBBZNZVRD-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲基甲基醚 、 (1S,2R)-1-Acetylamino-2-methyl-1,2-dihydro-naphthalene-2-carboxylic acid 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (1S,2R)-1-Acetylamino-2-methyl-1,2-dihydro-naphthalene-2-carboxylic acid methoxymethyl 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
• 作为产物：
  描述：

  2-(2'-Naphthyl)-4-(S)-tert-butyloxazoline 在 盐酸 、 六甲基磷酰三胺 、 sodium hydroxide 、 正丁基锂 、 正丁胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.83h， 生成 (1S,2R)-1-Acetylamino-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

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.