(1S)-1-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]ethanol | 1196958-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S)-1-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]ethanol
• CAS: 1196958-28-7
• 化学式: C₁₀H₉BrN₂O₂
• 分子量: 269.098
• InChiKey: IQKUUYCXYHTFQR-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]ethanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以60%的产率得到1-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]ethanone
  参考文献：
  名称：

  Efficient Chemoenzymatic Dynamic Kinetic Resolution of 1-Heteroaryl Ethanols

  摘要：

  The scope and limitation of the combined rutheinum-lipase induced dynamic kinetic resolution (DKR) through O-acetylation of racemic heteroaromatic secondary alcohols, i.e., 1-heteroaryl substituted ethanols, was investigated. After initial screening of reaction conditions, Candida antarctica lipase B (Novozyme 435, N435) together with 4-chloro-phenylacetate as acetyl-donor for kinetic resolution (KR), in conjunction with the ruthenium-based Shvo catalyst for substrate racemization in toluene at 80 degrees C, enabled DKR with high yields and stereoselectivity of various 1-heteroaryl ethanols, Such as oxadiazoles, isoxazoles, 1H-pyrazole, or 1H-imidazole. In addition, DFT calculations based on a simplified catalyst complex model for the catalytic (de)hydrogenation step are in agreement with the previously reported outer sphere mechanism. These results support the further understanding of the mechanistic aspects behind the difference in reactivity of 1-heteroaryl substituted ethanols in comparison to reference substrates, as often referred to in the literature.

  DOI：

  10.1021/jo901987z
• 作为产物：
  描述：

  L-乳酸 、 (E)-4-溴-N’-羟基苄脒 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 、 乙醇 为溶剂， 反应 11.0h， 以35%的产率得到(1S)-1-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]ethanol
  参考文献：
  名称：

  Efficient Chemoenzymatic Dynamic Kinetic Resolution of 1-Heteroaryl Ethanols

  摘要：

  The scope and limitation of the combined rutheinum-lipase induced dynamic kinetic resolution (DKR) through O-acetylation of racemic heteroaromatic secondary alcohols, i.e., 1-heteroaryl substituted ethanols, was investigated. After initial screening of reaction conditions, Candida antarctica lipase B (Novozyme 435, N435) together with 4-chloro-phenylacetate as acetyl-donor for kinetic resolution (KR), in conjunction with the ruthenium-based Shvo catalyst for substrate racemization in toluene at 80 degrees C, enabled DKR with high yields and stereoselectivity of various 1-heteroaryl ethanols, Such as oxadiazoles, isoxazoles, 1H-pyrazole, or 1H-imidazole. In addition, DFT calculations based on a simplified catalyst complex model for the catalytic (de)hydrogenation step are in agreement with the previously reported outer sphere mechanism. These results support the further understanding of the mechanistic aspects behind the difference in reactivity of 1-heteroaryl substituted ethanols in comparison to reference substrates, as often referred to in the literature.

  DOI：

  10.1021/jo901987z