1-[3-(4-chloro-phenyl)-isothiazol-4-yl]-ethanone | 1196958-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-(4-chloro-phenyl)-isothiazol-4-yl]-ethanone
• 英文别名: 1-[3-(4-Chlorophenyl)-1,2-thiazol-4-yl]ethanone
• CAS: 1196958-38-9
• 化学式: C₁₁H₈ClNOS
• 分子量: 237.71
• InChiKey: ZDLXYSQQCBQNPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,4-噁噻唑-2-酮,5-(4-氯苯基)- 、 3-丁炔-2-酮 反应 9.0h， 以32%的产率得到1-[3-(4-chloro-phenyl)-isothiazol-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

文献信息

• 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.