(S)-(-)-1-(3,4-dimethoxyphenyl)ethylamine hydrochloride

• 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)-(-)-1-(3,4-dimethoxyphenyl)ethylamine hydrochloride
• 英文别名: (S)-1-(3,4-dimethoxyphenyl)ethan-1-aminium chloride；[(1S)-1-(3,4-dimethoxyphenyl)ethyl]azanium;chloride
• 化学式: C₁₀H₁₅NO₂*ClH
• mdl: MFCD24422996
• 分子量: 217.696
• InChiKey: PQHFDOBOSKIMTO-FJXQXJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-(-)-N-(3,4-dimethoxybenzylidene)-2-methylpropanesulfinamide 在 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.5h， 生成 (S)-(-)-1-(3,4-dimethoxyphenyl)ethylamine hydrochloride
  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

• Chiral Brønsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH–Imine Hydrochloride Salts
  作者：Benjamin List、Vijay N. Wakchaure、Carla Obradors

  DOI：10.1055/s-0040-1706413

  日期：2020.10

  are frequently used substrates in asymmetric Bronsted acid catalysis, their corresponding salts are generally considered unsuitable reaction partners. Such processes are challenging because they require the successful competition of a catalytic amount of a chiral anion with a stoichiometric amount of an achiral one. We now show that enantiopure disulfonimides enable the asymmetric reduction of N–H imine

  虽然亚胺是不对称布朗斯台德酸催化中经常使用的底物，但它们相应的盐通常被认为是不合适的反应伙伴。这些过程具有挑战性，因为它们需要催化量的手性阴离子与化学计量量的非手性阴离子成功竞争。我们现在表明，使用 Hantzsch 酯作为氢源，对映体纯二磺酰亚胺能够不对称还原 N-H 亚胺盐酸盐。我们的可扩展反应以高效率和对映选择性提供结晶伯胺盐，这一发现表明这种方法在其他布朗斯台德酸催化的非手性亚胺盐转化中具有潜力。动力学研究和酸度数据表明双功能催化活化模式。
• 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.