(1R,2R)-2-<(β-hydroxy-α-methylphenethyl)methylamino>-N,N-dimethylacetamide | 139528-26-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R)-2-<(β-hydroxy-α-methylphenethyl)methylamino>-N,N-dimethylacetamide
• 英文别名: 2-[[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-methylamino]-N,N-dimethylacetamide
• CAS: 139528-26-0
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: CACRSPQOIJJSPZ-RISCZKNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.78
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-<(β-hydroxy-α-methylphenethyl)methylamino>-N,N-dimethylacetamide 在 lithium aluminium tetrahydride 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 (1R,2R)-α-<1-<<2-(dimethylamino)ethyl>methylamino>ethyl>-N-phenylbenzylamine
  参考文献：
  名称：

  Stereo- and regioselective synthesis of chiral diamines and triamines from pseudoephedrine and ephedrine

  摘要：

  N-Alkylated derivatives of (1R,2R)-(-)-pseudoephedrine and (1R,2S)-(-)-ephedrine afford, upon reaction with methanesulfonyl chloride, mixtures of 1-chloro- and 2-chloroamines which undergo stereospecific and regiospecific substitution reactions with sodium azide, amines, imides, thiols, thiolacetic acid, N-hydroxyphthalimide, and diphenylphosphine to give, in each case, a single isomeric product. These substitution reactions proceed with net retention of configuration. The procedure is not readily extended to nonbenzylic systems which give widely varying yields and regioisomeric ratios. The methodology provides for a facile synthesis of chiral diamines, triamines, aminohydroxylamines, aminothiols, aminosulfides, and aminophosphines from chiral 1,2-amino alcohols wherein either the amine or alcohol functionality is benzylic.

  DOI：

  10.1021/jo00032a013
• 作为产物：
  描述：

  左旋伪麻黄碱 、 2-氯-N,N-二甲基乙酰胺 在 三乙胺 作用下， 以 苯 为溶剂， 反应 8.0h， 以94%的产率得到(1R,2R)-2-<(β-hydroxy-α-methylphenethyl)methylamino>-N,N-dimethylacetamide
  参考文献：
  名称：

  Stereo- and regioselective synthesis of chiral diamines and triamines from pseudoephedrine and ephedrine

  摘要：

  N-Alkylated derivatives of (1R,2R)-(-)-pseudoephedrine and (1R,2S)-(-)-ephedrine afford, upon reaction with methanesulfonyl chloride, mixtures of 1-chloro- and 2-chloroamines which undergo stereospecific and regiospecific substitution reactions with sodium azide, amines, imides, thiols, thiolacetic acid, N-hydroxyphthalimide, and diphenylphosphine to give, in each case, a single isomeric product. These substitution reactions proceed with net retention of configuration. The procedure is not readily extended to nonbenzylic systems which give widely varying yields and regioisomeric ratios. The methodology provides for a facile synthesis of chiral diamines, triamines, aminohydroxylamines, aminothiols, aminosulfides, and aminophosphines from chiral 1,2-amino alcohols wherein either the amine or alcohol functionality is benzylic.

  DOI：

  10.1021/jo00032a013

文献信息

• Stereo- and regioselective synthesis of chiral diamines and triamines from pseudoephedrine and ephedrine
  作者：R. Karl Dieter、Niranjan Deo、Bharat Lagu、Janice W. Dieter

  DOI：10.1021/jo00032a013

  日期：1992.3

  N-Alkylated derivatives of (1R,2R)-(-)-pseudoephedrine and (1R,2S)-(-)-ephedrine afford, upon reaction with methanesulfonyl chloride, mixtures of 1-chloro- and 2-chloroamines which undergo stereospecific and regiospecific substitution reactions with sodium azide, amines, imides, thiols, thiolacetic acid, N-hydroxyphthalimide, and diphenylphosphine to give, in each case, a single isomeric product. These substitution reactions proceed with net retention of configuration. The procedure is not readily extended to nonbenzylic systems which give widely varying yields and regioisomeric ratios. The methodology provides for a facile synthesis of chiral diamines, triamines, aminohydroxylamines, aminothiols, aminosulfides, and aminophosphines from chiral 1,2-amino alcohols wherein either the amine or alcohol functionality is benzylic.