(2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methyl-3-phenylpropylamine | 322392-11-0

• 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: (2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methyl-3-phenylpropylamine
• 英文别名: (2S)-2-(3,4-dimethoxyphenyl)-N-methyl-3-phenylpropan-1-amine
• CAS: 322392-11-0
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: GIPFDKWWIQTNJR-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methyl-3-phenylpropylamine 在 盐酸 作用下， 反应 16.0h， 以93%的产率得到(4S)-(+)-4-benzyl-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline
  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 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 、 sodium cyanoborohydride 、 sodium sulfate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， -78.0~20.0 ℃ 、202.65 kPa 条件下， 反应 9.58h， 生成 (2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methyl-3-phenylpropylamine
  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.