(S)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanol | 1492020-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanol
• 英文别名: (1S)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanol
• CAS: 1492020-36-6
• 化学式: C₉H₁₀BrFO₂
• 分子量: 249.08
• InChiKey: QMDJXHXWLAYLAK-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-1-(3-氟-4-甲氧基苯基)乙酮 在 Almag CRED A₁₆₁ 、 NADP 、 glucose dehydrogenase 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 以24%的产率得到(S)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanol
  参考文献：
  名称：

  Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology

  摘要：

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.015

文献信息

• Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology
  作者：Andrew S. Rowan、Thomas S. Moody、Roger M. Howard、Toby J. Underwood、Iain R. Miskelly、Yanan He、Bo Wang

  DOI：10.1016/j.tetasy.2013.09.015

  日期：2013.11

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.