(S)-(-)-N-(2,2-diethoxyethyl)-1-(3,4-dimethoxyphenyl)ethylamine

• 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: (S)-(-)-N-(2,2-diethoxyethyl)-1-(3,4-dimethoxyphenyl)ethylamine
• 英文别名: N-[(1S)-1-(3,4-dimethoxyphenyl)ethyl]-2,2-diethoxyethanamine
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: JHAGISKMVHDGPB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-(2,2-diethoxyethyl)-1-(3,4-dimethoxyphenyl)ethylamine 在 盐酸 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到猪毛菜定
  参考文献：
  名称：

  Diastereoselective Pomeranz–Fritsch–Bobbitt synthesis of (S)-(−)-salsolidine using (R)-N-tert-butanesulfinylimine as a substrate

  摘要：

  The highly diastereoselective addition of methyl Grignard reagent to chiral (R)-N-tert-butanesulfinylimine 8 was the key step in the synthesis of (S)-(-)-salsolidine 1 of high enantiomeric purity. The resulting addition product, tert-butanesulfinylamide 9, was then subjected to cyclization via amine 10 and Pomeranz-Fritsch aminoacetal 11. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.05.011
• 作为产物：
  描述：

  2-溴-1,1-二乙氧基乙烷 、 (S)-1-(3,4-二甲氧基苯基)乙胺 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以62%的产率得到(S)-(-)-N-(2,2-diethoxyethyl)-1-(3,4-dimethoxyphenyl)ethylamine
  参考文献：
  名称：

  Diastereoselective Pomeranz–Fritsch–Bobbitt synthesis of (S)-(−)-salsolidine using (R)-N-tert-butanesulfinylimine as a substrate

  摘要：

  The highly diastereoselective addition of methyl Grignard reagent to chiral (R)-N-tert-butanesulfinylimine 8 was the key step in the synthesis of (S)-(-)-salsolidine 1 of high enantiomeric purity. The resulting addition product, tert-butanesulfinylamide 9, was then subjected to cyclization via amine 10 and Pomeranz-Fritsch aminoacetal 11. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.05.011

文献信息

• Diastereoselective Pomeranz–Fritsch–Bobbitt synthesis of (S)-(−)-salsolidine using (R)-N-tert-butanesulfinylimine as a substrate
  作者：Agnieszka Kościołowicz、Maria D. Rozwadowska

  DOI：10.1016/j.tetasy.2006.05.011

  日期：2006.5

  The highly diastereoselective addition of methyl Grignard reagent to chiral (R)-N-tert-butanesulfinylimine 8 was the key step in the synthesis of (S)-(-)-salsolidine 1 of high enantiomeric purity. The resulting addition product, tert-butanesulfinylamide 9, was then subjected to cyclization via amine 10 and Pomeranz-Fritsch aminoacetal 11. (c) 2006 Elsevier Ltd. All rights reserved.