(S,S)-α-(benzo[d][1,3]dioxol-5-yl)-α-[1-(4-methoxyphenyl)ethylamino]acetonitrile hydrochloride | 1313219-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (S,S)-α-(benzo[d][1,3]dioxol-5-yl)-α-[1-(4-methoxyphenyl)ethylamino]acetonitrile hydrochloride
• 英文别名: (2S)-2-(1,3-benzodioxol-5-yl)-2-[[(1S)-1-(4-methoxyphenyl)ethyl]amino]acetonitrile;hydrochloride
• CAS: 1313219-25-8
• 化学式: C₁₈H₁₈N₂O₃*ClH
• 分子量: 346.813
• InChiKey: PJWSWTHVEPCDRW-CVHDTDHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S,S)-α-(benzo[d][1,3]dioxol-5-yl)-α-[1-(4-methoxyphenyl)ethylamino]acetonitrile hydrochloride 在 盐酸 、 水 作用下， 生成 (S)-α-amino-α(benzo[d]dioxol-5-yl)acetic acid hydrochloride 、 (R)-α-amino-α(benzo[d]dioxol-5-yl)acetic acid hydrochloride
  参考文献：
  名称：

  Asymmetric Strecker Synthesis of α-Arylglycines

  摘要：

  A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure alpha-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4-methoxyphenyl)ethylamine affords highly crystalline (S,S)-alpha-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-alpha-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-alpha-arylglycines. The enantiopurities of these (S)-a-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by H-1 NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.

  DOI：

  10.1021/jo200528s
• 作为产物：
  描述：

  (S)-(-)-1-(4-甲氧基苯基)乙胺盐酸盐 、 sodium cyanide 、 胡椒醛 以 甲醇 、 水 为溶剂， 反应 16.0h， 以54%的产率得到(S,S)-α-(benzo[d][1,3]dioxol-5-yl)-α-[1-(4-methoxyphenyl)ethylamino]acetonitrile hydrochloride
  参考文献：
  名称：

  Asymmetric Strecker Synthesis of α-Arylglycines

  摘要：

  A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure alpha-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4-methoxyphenyl)ethylamine affords highly crystalline (S,S)-alpha-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-alpha-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-alpha-arylglycines. The enantiopurities of these (S)-a-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by H-1 NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.

  DOI：

  10.1021/jo200528s

文献信息

• Asymmetric Strecker Synthesis of α-Arylglycines
  作者：Yolanda Pérez-Fuertes、James E. Taylor、David A. Tickell、Mary F. Mahon、Steven D. Bull、Tony D. James

  DOI：10.1021/jo200528s

  日期：2011.8.5

  A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure alpha-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4-methoxyphenyl)ethylamine affords highly crystalline (S,S)-alpha-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-alpha-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-alpha-arylglycines. The enantiopurities of these (S)-a-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by H-1 NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.