(+/-)-methyl 3-cyano-2-(6-methoxy-2-naphthyl)propionate | 674776-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-methyl 3-cyano-2-(6-methoxy-2-naphthyl)propionate
• 英文别名: Methyl 3-cyano-2-(6-methoxynaphthalen-2-yl)propanoate
• CAS: 674776-28-4
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: KHSNQFOQUPKOJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl 3-cyano-2-(6-methoxy-2-naphthyl)propionate 在 sodium hydroxide 、 3 A molecular sieve 、 五氯化磷 、 三乙胺 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 为溶剂， 生成 (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2S)-3-cyano-2-(6-methoxy-2-naphthyl)propionate
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids

  摘要：

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.035
• 作为产物：
  描述：

  甲基 6-甲氧基-2-萘乙酸酯 、 溴乙腈 在 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以73%的产率得到(+/-)-methyl 3-cyano-2-(6-methoxy-2-naphthyl)propionate
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids

  摘要：

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.035

文献信息

• Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids
  作者：Pelayo Camps、Diego Muñoz-Torrero、Laura Sánchez

  DOI：10.1016/j.tetasy.2003.10.035

  日期：2004.1

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.