1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethanol | 660417-33-4

• 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: 1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethanol
• 英文别名: 1-(5-(3-Chlorophenyl)-1,3,4-oxadiazol-2-yl)ethanol
• CAS: 660417-33-4
• 化学式: C₁₀H₉ClN₂O₂
• 分子量: 224.647
• InChiKey: PGNXNYAMBCXBKO-UHFFFAOYSA-N

物化性质

• 沸点：
  382.6±52.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：

  1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethanol 、 乙酸-4-氯苯酯 在 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 (1S)-1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethyl acetate 、 (1R)-1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethyl acetate
  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：

  1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]ethyl acetate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以76%的产率得到1-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-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

文献信息

• Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
  申请人：Edwards Louise

  公开号：US20050272779A1

  公开（公告）日：2005-12-08

  The present invention relates to new compounds of formula I, to pharmaceutical formulations containing the compounds, and to the use of the compounds in the prevention and/or treatment of mGluR5 receptor-mediated disorders.

  本发明涉及公式I的新化合物，包含该化合物的药物配方，以及利用该化合物预防和/或治疗mGluR5受体介导的疾病的用途。
• Compounds
  申请人：Arora Jalaj

  公开号：US20060122397A1

  公开（公告）日：2006-06-08

  The present invention relates to new compounds of formula I, a process for their preparation and new intermediates prepared therein, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.

  本发明涉及化合物I的新化合物，其制备过程和其中制备的新中间体，含有该化合物的制药配方以及在治疗中使用该化合物的用途。
• ADDITIONAL HETEROPOLYCYCLIC COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：Edwards Louise

  公开号：US20080045571A1

  公开（公告）日：2008-02-21

  The present invention relates to new compounds of formula I, to pharmaceutical formulations containing the compounds, and to the use of the compounds in the prevention and/or treatment of mGluR5 receptor-mediated disorders.

  本发明涉及公式I的新化合物，包括含有该化合物的制药配方，以及该化合物在预防和/或治疗mGluR5受体介导的疾病中的使用。
• [EN] "1,2,4"OXADIAZOLES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5<br/>[FR] NOUVEAUX COMPOSES
  申请人：ASTRAZENECA AB

  公开号：WO2004014881A3

  公开（公告）日：2004-05-27
• NEW COMPOUNDS
  申请人：Astra Zeneca AB

  公开号：EP1529045A2

  公开（公告）日：2005-05-11