(1S)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethanol | 1196958-60-7

• 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: (1S)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethanol
• 英文别名: (S)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanol；(1S)-1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethanol
• CAS: 1196958-60-7
• 化学式: C₁₁H₁₀ClNO₂
• 分子量: 223.659
• InChiKey: FOLGHHVVTIHOLE-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸-4-氯苯酯 、 (1S)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethanol 在 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) 作用下， 以 甲苯 为溶剂， 反应 66.0h， 以10%的产率得到(1R)-1-[5-(3-chlorophenyl)isoxazol-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
• 作为产物：
  描述：

  1-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethanone 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (S,S)-N-(2,3,4,5,6-pentamethylbenzenesulfonyl)-1,2-diphenylethylenediamine 甲酸 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， 反应 2.0h， 以93.8%的产率得到
  参考文献：
  名称：

  [EN] NEW PROCESS FOR THE PREPARATION OF 1- [5- (3-CHLORO-PHENYL) - ISOOXAZOL-3-YL] -ETHANONE AND (R) -1- [5- (3-CHLORO-PHENYL) - ISOOXAZOL-3-YL] -ETHANOL
  [FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE DE LA 1-[5-(3-CHLORO-PHÉNYL)-ISOXAZOL-3-YL]-ÉTHANONE ET DU (R)-1-[5-(3-CHLORO-PHÉNYL)-ISOXAZOL-3-YL]-ÉTHANOL

  摘要：

  本发明提供了一种制备化合物1-[5-(3-氯苯基)-异噁唑-3-基]-乙酮的方法：其中将化合物5-(3-氯苯基)-异噁唑-3-羧酸酯与CH3MgX反应。本发明还提供了(R)-1-[5-(3-氯苯基)-异噁唑-3-基]-乙醇的制备方法：其中1-[5-(3-氯苯基)-异噁唑-3-基]-乙酮被还原为(R)-1-[5-(3-氯苯基)-异噁唑-3-基]-乙醇。

  公开号：

  WO2010071558A1

文献信息

• PROCESS FOR THE PREPARATION OF 1-[5-(3-CHLORO-PHENYL)-ISOOXAZOL-3-YL]-ETHANONE AND (R)-1-[5-(3-CHLORO-PHENYL)-ISOOXAZOL-3-YL]-ETHANOL
  申请人：Åström Hans

  公开号：US20110313172A1

  公开（公告）日：2011-12-22

  The present invention provides a process for the preparation of the compound 1-[5-(3-chloro-phenyl)-isooxazol-3-yl]-ethanone: Wherein the compound 5-(3-chlorophenyl)-isooxazol-3-carboxylate is reacted with CH3MgX. The present invention also provides a process for the preparation of (R)-1-[5-(3-chloro-phenyl)-isooxazol-3-yl]-ethanol: Wherein 1-[5-(3-chloro-phenyl)-isooxazol-3-yl]-ethanone is reduced to (R)-1-[5-(3-chloro-phenyl)-isooxazol-3-yl]-ethanol.

  本发明提供了一种制备化合物1-[5-(3-氯苯基)-异恶唑-3-基]-乙酮的方法：其中，化合物5-(3-氯苯基)-异恶唑-3-羧酸酯与CH3MgX反应。本发明还提供了一种制备(R)-1-[5-(3-氯苯基)-异恶唑-3-基]-乙醇的方法：其中，化合物1-[5-(3-氯苯基)-异恶唑-3-基]-乙酮被还原为(R)-1-[5-(3-氯苯基)-异恶唑-3-基]-乙醇。
• Efficient Chemoenzymatic Dynamic Kinetic Resolution of 1-Heteroaryl Ethanols
  作者：Karl S. A. Vallin、David Wensbo Posaric、Zdenko Hameršak、Mats A. Svensson、Alexander B. E. Minidis

  DOI：10.1021/jo901987z

  日期：2009.12.18

  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.
• [EN] NEW PROCESS FOR THE PREPARATION OF 1- [5- (3-CHLORO-PHENYL) - ISOOXAZOL-3-YL] -ETHANONE AND (R) -1- [5- (3-CHLORO-PHENYL) - ISOOXAZOL-3-YL] -ETHANOL<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE DE LA 1-[5-(3-CHLORO-PHÉNYL)-ISOXAZOL-3-YL]-ÉTHANONE ET DU (R)-1-[5-(3-CHLORO-PHÉNYL)-ISOXAZOL-3-YL]-ÉTHANOL
  申请人：ASTRAZENECA AB

  公开号：WO2010071558A1

  公开（公告）日：2010-06-24

  The present invention provides a process for the preparation of the compound 1- [5- (3-chloro-phenyl) -isooxazol-3-yl] - ethanone: Wherein the compound 5- (3-chlorophenyl) -isooxazol-3- carboxylate is reacted with CH3MgX. The present invention also provides a process for the preparation of (R) -1- [5- ( 3-chloro-phenyl) -isooxazol-3-yl] - ethanol : Wherein 1- [5- (3-chloro-phenyl) -isooxazol-3-yl] -ethanone is reduced to (R) -1- [5- (3-chloro-phenyl) -isooxazol-3-yl] -ethanol.

  本发明提供了一种制备化合物1-[5-(3-氯苯基)-异噁唑-3-基]-乙酮的方法：其中将化合物5-(3-氯苯基)-异噁唑-3-羧酸酯与CH3MgX反应。本发明还提供了(R)-1-[5-(3-氯苯基)-异噁唑-3-基]-乙醇的制备方法：其中1-[5-(3-氯苯基)-异噁唑-3-基]-乙酮被还原为(R)-1-[5-(3-氯苯基)-异噁唑-3-基]-乙醇。