(1R,2'S)-(-)-N-[2'-(3,4-dimethoxyphenyl)propyl]-2-methoxy-1-phenylethylamine | 322392-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2'S)-(-)-N-[2'-(3,4-dimethoxyphenyl)propyl]-2-methoxy-1-phenylethylamine
• 英文别名: (2S)-2-(3,4-dimethoxyphenyl)-N-[(1R)-2-methoxy-1-phenylethyl]propan-1-amine
• CAS: 322392-01-8
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: AQMAPOIOWQLUJP-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2'S)-(-)-N-[2'-(3,4-dimethoxyphenyl)propyl]-2-methoxy-1-phenylethylamine 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium cyanoborohydride 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 6.0h， 生成 (2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methylpropylamine
  参考文献：
  名称：

  Stereocontrolled metalloenamine alkylations: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  A procedure for the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines is described. The key step in the synthetic route is a stereocontrolled metalloenamine alkylation using (R)-(+)-phenyl-glycinol methyl ether as the chiral auxiliary. Subsequent N-methylation, hydrogenolysis and cyclization afforded the target heterocycles with enantiomeric excesses higher than 99%. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00343-8
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙醛 在 sodium tetrahydroborate 、 sodium sulfate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 3.58h， 生成 (1R,2'S)-(-)-N-[2'-(3,4-dimethoxyphenyl)propyl]-2-methoxy-1-phenylethylamine
  参考文献：
  名称：

  Stereocontrolled metalloenamine alkylations: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  A procedure for the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines is described. The key step in the synthetic route is a stereocontrolled metalloenamine alkylation using (R)-(+)-phenyl-glycinol methyl ether as the chiral auxiliary. Subsequent N-methylation, hydrogenolysis and cyclization afforded the target heterocycles with enantiomeric excesses higher than 99%. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00343-8

文献信息

• Stereocontrolled metalloenamine alkylations: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines
  作者：Jose L Vicario、Dolores Badı́a、Esther Domı́nguez、Luisa Carrillo

  DOI：10.1016/s0957-4166(00)00343-8

  日期：2000.9

  A procedure for the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines is described. The key step in the synthetic route is a stereocontrolled metalloenamine alkylation using (R)-(+)-phenyl-glycinol methyl ether as the chiral auxiliary. Subsequent N-methylation, hydrogenolysis and cyclization afforded the target heterocycles with enantiomeric excesses higher than 99%. (C) 2000 Elsevier Science Ltd. All rights reserved.