(1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanol | 474126-06-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanol
• 英文别名: (1R,2S)-2-amino-2-(1,3-benzodioxol-5-yl)-1-(3,4-dimethoxyphenyl)ethanol
• CAS: 474126-06-2
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: SECKOKIFVLDDIG-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以84%的产率得到(1R,2S)-(-)-2-[dimethyl(2,2-dimethylethyl)-silyloxy]-2-(3,4-dimethoxyphenyl)-1-(3,4-methylenedioxyphenyl)ethylamine
  参考文献：
  名称：

  Asymmetric synthesis of 1,2-diaryl-2-amino ethanols

  摘要：

  A straightforward procedure for the asymmetric synthesis of 1,2-diaryl-2-amino ethanols is described. The key step relies on the diastereoselective electrophilic amination of the enolates derived from the corresponding (S,S)-(+)-pseudoephedrine arylacetamides with di-tert-butylazodicarboxylate, followed by a hydrolysis/hydrogenolysis procedure to yield alpha-amino amide derivatives with a very high degree of diastereoselection. These substrates were subsequently Subjected to a non-racemizing 1,2-addition step with several aryllithium reagents to yield the corresponding alpha-amino ketones which, upon diastereoselective reduction with NaBH4 afforded the desired beta-amino alcohols as single enantiomers with 1,2-anti relative configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00181-7
• 作为产物：
  描述：

  (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 在 sodium tetrahydroborate 、 正丁基锂 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1R,2S)-(-)-2-amino-1-(3,4-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanol
  参考文献：
  名称：

  Asymmetric synthesis of 1,2-diaryl-2-amino ethanols

  摘要：

  A straightforward procedure for the asymmetric synthesis of 1,2-diaryl-2-amino ethanols is described. The key step relies on the diastereoselective electrophilic amination of the enolates derived from the corresponding (S,S)-(+)-pseudoephedrine arylacetamides with di-tert-butylazodicarboxylate, followed by a hydrolysis/hydrogenolysis procedure to yield alpha-amino amide derivatives with a very high degree of diastereoselection. These substrates were subsequently Subjected to a non-racemizing 1,2-addition step with several aryllithium reagents to yield the corresponding alpha-amino ketones which, upon diastereoselective reduction with NaBH4 afforded the desired beta-amino alcohols as single enantiomers with 1,2-anti relative configuration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00181-7