(1R,2S)-2-(isobutyl(methyl)amino)-1-phenylpropan-1-ol

• 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,2S)-2-(isobutyl(methyl)amino)-1-phenylpropan-1-ol
• 英文别名: (1R,2S)-N-isobutyl-N-methylnorephedrine；(1R,2S)-2-[methyl(2-methylpropyl)amino]-1-phenylpropan-1-ol
• 化学式: C₁₄H₂₃NO
• 分子量: 221.343
• InChiKey: ARDALYZLLAOSQD-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴代异丁烷 、 麻黄碱 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到(1R,2S)-2-(isobutyl(methyl)amino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  A structural examination of the impact of oxygenated side chains in Ephedra compounds in the catalytic asymmetric addition of diethylzinc to aldehydes

  摘要：

  An investigation of the impact of oxygenated side chains in Ephedra compounds on the catalytic asymmetric addition of diethylzinc to aldehydes has been conducted. (1R,2S)-Ephedrine and (1S,2S)-pseudoephedrine were alkylated with either alkyl halides or beta-alkoxyalkyl halides to afford a series of ligands 9a-h and 10a-h. These compounds were employed in the enantioselective addition of diethylzinc to a variety of aldehydes. It was determined that the presence of oxygen could have a negative effect in terms of obtaining high levels of enantiomeric discrimination, but the effect is diminished with higher levels of substitution near the oxygen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.028

文献信息

• Nitriles under palladium-catalyzed hydrogenation conditions as substitutes for aldehydes in the reaction with 1,2-amino alcohols: Formation of 1,3-oxazolidines and reductive N-alkylation
  作者：Françoise Hénin、Stéphane Létinois、Jacques Muzart

  DOI：10.1016/s0040-4039(97)01728-0

  日期：1997.10

  hydrogen and catalytic amounts of Pd/C induced the formation of 1,3-oxazolidines from nitriles and 1,2-amino alcohols. The subsequent reductive cleavage of the NCO bond of these heterocycles occurred under the same conditions. Thus, this methodology provides a new one-pot N-alkylation of 1,2-amino alcohols using nitriles as reagents with yields up to 98%.

  在室温下，氢的存在和催化量的Pd / C导致腈和1,2-氨基醇形成1,3-恶唑烷。这些杂环的NC ＝ O键的随后还原裂解在相同条件下发生。因此，该方法使用腈作为试剂，提供了新的一锅法1,2-氨基醇的N-烷基化反应，收率高达98％。
• Dimethylzinc-Mediated, Enantioselective Synthesis of Propargylic Amines
  作者：Lorenzo Zani、Torsten Eichhorn、Carsten Bolm

  DOI：10.1002/chem.200601347

  日期：2007.3.16

  A one-pot, enantioselective synthesis of N-aryl propargylic amines, using alkynylation reagents obtained from dimethylzinc and terminal acetylenes in combination with various aldehydes and o-methoxyaniline as starting materials, has been developed. Enantiopure beta-amino alcohols derived from norephedrine were used as non-covalent chiral auxiliaries, both in stoichiometric or substoichiometric amount

  已经开发出一种N-芳基炔丙基胺的一锅，对映选择性合成，该合成使用得自二甲基锌和末端乙炔的炔基化试剂与各种醛和邻甲氧基苯胺相结合作为起始原料。衍生自去甲麻黄碱的对映体纯β-氨基醇以化学计量或亚化学计量的量用作非共价手性助剂。优化后，可以以高到高的收率（最高93％）和中等到高的对映体过量（最高ee达97％）获得炔丙基胺。证明了反应后回收手性助剂的可能性。
• Process For the Manufacture of Substituted Propionic Acids
  申请人：McCormack Peter

  公开号：US20080242876A1

  公开（公告）日：2008-10-02

  The invention concerns a process for the manufacture of substituted propionic acids comprising providing a substrate of formula (I): And subjecting the substrate to enantioselective hydrogenation under enantioselective hydrogenation conditions in the presence of an enantioselective hydrogenation catalyst comprising a catalyst ligand having a metallocene group with a chiral phosphorus or arsenic substituent to provide in enantiomeric excess a product of formula (II): or its enantiomer or if applicable its diastereomer.

  该发明涉及一种制备取代丙酸的方法，包括提供公式(I)的底物，并在手性氢化条件下，在手性氢化催化剂的存在下进行手性氢化，所述手性氢化催化剂包括具有带有手性磷或砷取代基的金属茂基的催化剂配体，以提供公式(II)的产物，或其对映异构体或如适用的对映体。