(R)-salbutamol acetate | 35459-13-3

• 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: (R)-salbutamol acetate
• 英文别名: acetic acid;4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
• CAS: 35459-13-3
• 化学式: C₂H₄O₂*C₁₃H₂₁NO₃
• 分子量: 299.367
• InChiKey: FNSZTAIRFCUOBB-YDALLXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  沙丁胺醇 在 三氟化硼乙醚 、 水 作用下， 反应 6.0h， 生成 (R)-salbutamol acetate
  参考文献：
  名称：

  Resolution of albuterol acetonide

  摘要：

  The (R)-enantiomer of albuterol has been isolated via resolution of albuterol acetonide with (2S,3S)-di-O-benzoyl- or (2S,3S)-di-O-toluoyltartaric acid. The absolute configuration of the resolved acetonide was assessed by H-1 NMR analysis of its (R)-Mosher's ester, and confirmed by an X-ray crystal structure determination of the (R)-phenylethylurea derivative of the (S)-enantiomer. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00209-8

文献信息

• Efficient Synthesis of 2‐Amino‐1‐Arylethanols Through a Lewis Base‐Catalyzed SiCl ₄ ‐Mediated Asymmetric Passerini‐Type Reaction
  作者：Aurélie Gernet、Virginie Ratovelomanana‐Vidal、Jean‐Luc Pirat、David Virieux、Tahar Ayad

  DOI：10.1002/ejoc.202001172

  日期：2020.11.8

  An atom economical and metal‐free, one‐pot two‐step asymmetric synthesis of highly valuable 2‐amino‐1‐arylethanols has been established from commercially available starting materials. The effectiveness and scalability of our approach have been demonstrated via the synthesis of the Salbutamol acetate salt, a bronchodilator widely used to treat asthma.

  从市售的起始原料已经建立了一种原子经济，无金属，一锅两步不对称合成高价值的2-氨基-1-芳基乙醇。通过合成广泛用于治疗哮喘的支气管扩张剂醋酸沙丁胺醇盐，已证明了我们方法的有效性和可扩展性。
• Enantioselective Synthesis of Phenyl-ethanolamines Through Application of Chiral Sulfoxide
  作者：Aathimanivelu V. Sivakumar、Anand M. Lahoti、Sujata V. Bhat

  DOI：10.1080/00397910902765578

  日期：2009.8.20

  Abstract Efficient enantioselective synthesis of (R)- and (S)-enantiomers of 2-(tert-butylamino)-1-(p-methoxyphenyl)-ethanol has been achieved in high enantiomeric excess by using asymmetric sulfoxide as a chiral auxiliary. The present synthetic approach was further extended to the asymmetric synthesis of (R)-salbutamol.

  摘要 通过使用不对称亚砜作为手性助剂，以高对映体过量实现了 2-(叔丁基氨基)-1-(对甲氧基苯基)-乙醇的 (R)- 和 (S)- 对映体的高效对映选择性合成。目前的合成方法进一步扩展到 (R)-沙丁胺醇的不对称合成。
• Application of the Chiral Acyl Anion Equivalent, <i>trans</i>-1,3-Dithiane 1,3-Dioxide, to an Asymmetric Synthesis of (<i>R</i>)-Salbutamol
  作者：Varinder K. Aggarwal、Blanca N. Esquivel-Zamora

  DOI：10.1021/jo026410i

  日期：2002.11.1

  An enantioselective synthesis of (R)-salbutamol has been carried out using the chiral, C2 symmetric acyl anion equivalent, (1R,3R)-1,3-dithiane 1,3-dioxide, which undergoes addition to an aromatic aldehyde with very high stereocontrol at 0 degrees C. Pummerer reaction and work-up with lithium ethanethiolate generated the alpha-hydroxy thiolester in high yield and further transformations led to the

  （R）-沙丁胺醇的对映体选择性合成是使用手性，C2对称的酰基阴离子等价物（1R，3R）-1,3-二硫杂环丁烷1,3-二氧化物进行的，该芳香族醛具有非常高的芳香醛含量在0摄氏度下进行立体控制。Pummerer反应和乙硫醇锂的后处理以高收率产生α-羟基硫醇酯，进一步的转化导致目标化合物的对映体过量很高。
• Enantioselective Cobalt‐Catalyzed Hydroboration of Ketone‐Derived Silyl Enol Ethers
  作者：Wenke Dong、Zhiyang Ye、Wanxiang Zhao

  DOI：10.1002/anie.202117413

  日期：2022.7.18

  heteroatom-substituted alkenes is rarely explored and remains unprecedented, especially the earth-abundant metal catalyzed ones. Herein, the first cobalt-catalyzed asymmetric hydroboration of ketone-derived silyl enol ethers is reported, providing a convenient approach to access valuable enantiopure β-hydroxy boronic esters, which features broad substrate scope and excellent enantioselectivities.

  杂原子取代烯烃的催化不对称硼氢化反应很少被探索并且仍然是前所未有的，尤其是地球上丰富的金属催化的。本文报道了第一次钴催化的酮衍生甲硅烷基烯醇醚的不对称硼氢化反应，为获得有价值的对映纯 β-羟基硼酸酯提供了一种便捷的方法，该方法具有广泛的底物范围和优异的对映选择性。
• Resolution of albuterol acetonide
  作者：Mino R. Caira、Roger Hunter、Luigi R. Nassimbeni、Anne T. Stevens

  DOI：10.1016/s0957-4166(99)00209-8

  日期：1999.6

  The (R)-enantiomer of albuterol has been isolated via resolution of albuterol acetonide with (2S,3S)-di-O-benzoyl- or (2S,3S)-di-O-toluoyltartaric acid. The absolute configuration of the resolved acetonide was assessed by H-1 NMR analysis of its (R)-Mosher's ester, and confirmed by an X-ray crystal structure determination of the (R)-phenylethylurea derivative of the (S)-enantiomer. (C) 1999 Elsevier Science Ltd. All rights reserved.