(1S)-2-氯-1-(3-硝基苯基)乙醇 | 402937-69-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1S)-2-氯-1-(3-硝基苯基)乙醇
• 英文名称: (S)-2-chloro-1-(3-nitrophenyl)ethanol
• 英文别名: (1S)-2-chloro-1-(3-nitrophenyl)ethanol
• CAS: 402937-69-3
• 化学式: C₈H₈ClNO₃
• 分子量: 201.609
• InChiKey: AJHYSIGTVNOJDD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  alpha-氯乙酰苯 在 glucopyranose 、 硫酸 、 硝酸胍 作用下， 反应 78.0h， 生成 (R)-2-chloro-1-(3-nitrophenyl)ethanol 、 (1S)-2-氯-1-(3-硝基苯基)乙醇
  参考文献：
  名称：

  Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl)ethanol as a synthetic precursor for (R)-phenylephrine

  摘要：

  The incubated whole-cell biocatalyst of Pichia minuta JCM 3622 reduced 2-chloro-1-(3-nitrophenyl)ethanone to provide (R)-2-chloro-1-(3-nitrophenyl)ethanol with 99.2% ee in 87% isolated yield in the presence of Amberlite XAD-7 as a reservoir for the hydrophobic, crystalline and toxic substrate. The product was transformed to (R)-1-(3-hydroxyphenyl)-2-methylaminoethanol (PhenylePhrine,1a), a selective alpha(1)-adrenergic receptor agonist, in 98.0% ee over five steps. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.07.021

文献信息

• Tandem Concurrent Processes: One-Pot Single-Catalyst Biohydrogen Transfer for the Simultaneous Preparation of Enantiopure Secondary Alcohols
  作者：Fabricio R. Bisogno、Iván Lavandera、Wolfgang Kroutil、Vicente Gotor

  DOI：10.1021/jo802350f

  日期：2009.2.20

  A novel one-pot tandem biohydrogen transfer process to concurrently obtain two enantiopure sec-alcohols is presented; thus, using a suitable single enzyme and a catalytic amount of cofactor, several interesting building blocks could be easily achieved in an enantiocomplementary fashion, minimizing dramatically the quantity of reagents usually employed in the "coupled-substrate" approach.
• Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl)ethanol as a synthetic precursor for (R)-phenylephrine
  作者：Daisuke Tokoshima、Kengo Hanaya、Mitsuru Shoji、Takeshi Sugai

  DOI：10.1016/j.molcatb.2013.07.021

  日期：2013.12

  The incubated whole-cell biocatalyst of Pichia minuta JCM 3622 reduced 2-chloro-1-(3-nitrophenyl)ethanone to provide (R)-2-chloro-1-(3-nitrophenyl)ethanol with 99.2% ee in 87% isolated yield in the presence of Amberlite XAD-7 as a reservoir for the hydrophobic, crystalline and toxic substrate. The product was transformed to (R)-1-(3-hydroxyphenyl)-2-methylaminoethanol (PhenylePhrine,1a), a selective alpha(1)-adrenergic receptor agonist, in 98.0% ee over five steps. (C) 2013 Elsevier B.V. All rights reserved.