(1R)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl acetate | 870973-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1R)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl acetate
• 英文别名: (+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl acetate；[(1R)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl] acetate
• CAS: 870973-88-9
• 化学式: C₁₂H₁₁ClN₂O₃
• 分子量: 266.684
• InChiKey: REMXFUCXZXRZPZ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl acetate 、 单水氢氧化锂 在 Brine 、 乙酸乙酯 作用下， 以 tetrahydrofuran-water 为溶剂， 反应 18.0h， 以5.8 g (97%) of the title compound was obtained的产率得到(+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanol
  参考文献：
  名称：

  ADDITIONAL HETEROPOLYCYCLIC COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS

  摘要：

  本发明涉及公式I的新化合物，含有该化合物的药物配方以及在预防和/或治疗mGluR5受体介导的疾病中使用该化合物的方法。

  公开号：

  US20070293545A1
• 作为产物：
  描述：

  1-[5-(3-chloro-phenyl)-[1,2,4]oxadiazol-3-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 48.0h， 以39%的产率得到(1R)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-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

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。
• MgluR5 modulators
  申请人：Isaac Methvin

  公开号：US20080125436A1

  公开（公告）日：2008-05-29

  The present invention is directed to compounds of formula I: Wherein R 1 to R 5 , X and Z are further defined in the description. The invention also relates to processes for the preparation of the compounds and to intermediates used in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

  本发明涉及式I的化合物：其中R1至R5、X和Z在说明书中进一步定义。本发明还涉及制备该化合物的过程，以及用于制备中间体的中间体，含有该化合物的制药组合物，以及在治疗中使用该化合物。
• US7585881B2
  申请人：——

  公开号：US7585881B2

  公开（公告）日：2009-09-08
• US7772235B2
  申请人：——

  公开号：US7772235B2

  公开（公告）日：2010-08-10
• [EN] ADDITIONAL HETEROPOLYCYCLIC COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES HETEROPOLYCYCLIQUES SUPPLEMENTAIRES ET LEUR UTILISATION COMME ANTAGONISTES DU RECEPTEUR METABOTROPIQUE DU GLUTAMATE
  申请人：ASTRAZENECA AB

  公开号：WO2006014185A1

  公开（公告）日：2006-02-09

  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.