(1R,2'S)-(-)-N-[2'-(3,4-dimethoxyphenyl)-3'-phenylpropyl]-2-methoxy-1-phenylethylamine | 322392-04-1

• 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,2'S)-(-)-N-[2'-(3,4-dimethoxyphenyl)-3'-phenylpropyl]-2-methoxy-1-phenylethylamine
• 英文别名: (2S)-2-(3,4-dimethoxyphenyl)-N-[(1R)-2-methoxy-1-phenylethyl]-3-phenylpropan-1-amine
• CAS: 322392-04-1
• 化学式: C₂₆H₃₁NO₃
• 分子量: 405.537
• InChiKey: JPHSJOUVZOIOCR-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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)-3'-phenylpropyl]-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， 20.0~60.0 ℃ 、202.65 kPa 条件下， 反应 22.0h， 生成 (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 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)-3'-phenylpropyl]-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.