(S)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol | 1433187-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (S)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol
• 英文别名: (2S)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol
• CAS: 1433187-94-0
• 化学式: C₁₀H₁₁NOS₂
• 分子量: 225.335
• InChiKey: NPVCYDIKUKFSOH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-苯并噻唑基硫代)-2-丙酮 在 sodium tetrahydroborate 、 amano PS (native lipase from B_. cepacia earlier Pseudomonas cepacia) 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 308.0h， 生成 (S)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol with antifungal activity: a comparative study of transesterification versus hydrolysis

  摘要：

  A study of chemoenzymatic synthesis of both enantiomers of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol was carried out. Several commercially available lipase preparations were tested as biocatalysts in the kinetic resolution process of target compound by enantioselective transesterification and/or hydrolysis. CAL-B (Novozym 435) was found to be the optimal catalyst. The lipase-mediated hydrolysis approach appeared to be superior to the transesterification reaction. Absolute configuration of the obtained alcohol was postulated, applying modified Mosher's methodology. The inhibitory activity of the synthesized benzothiazole derivatives against pathogenic fungi was checked. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.014

文献信息

• Enantioselective Resolution Copolymerization of <i>Racemic</i> Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides
  作者：Jie Li、Bai-Hao Ren、Zhao-Qian Wan、Shi-Yu Chen、Ye Liu、Wei-Min Ren、Xiao-Bing Lu

  DOI：10.1021/jacs.9b02722

  日期：2019.6.5

  strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization

  在此，我们报告了一种通过外消旋末端环氧化物与酸酐的对映选择性拆分共聚制备全同立构聚酯和手性环氧化物的有效策略，由对映纯双金属配合物与亲核助催化剂共同介导。轴向接头和配体的二胺主链的手性是造成该动力学拆分共聚过程的手性诱导的原因。该催化剂体系表现出非凡的对映选择性水平，对于各种外消旋环氧化物的动力学分辨率超过 300，提供具有完全交替结构和低多分散指数的高度全同立构共聚物（选择性因子超过 300）。
• Asymmetric reduction of 1-(benzoazol-2-ylsulfanyl)propan-2-ones using whole cells of Mortierella isabellina, Debaryomyces hansenii, Geotrichum candidum and Zygosaccharomyces rouxii
  作者：Paweł Borowiecki、Małgorzata Włoczewska、Zbigniew Ochal

  DOI：10.1016/j.molcatb.2014.07.015

  日期：2014.11

  Growing cells of four fungal strains were used in reduction of 1-(benzoazol-2-ylsulfanyl)propan-2-ones 3a-c to corresponding (R)-(+)-1-(benzoazol-2-ylsulfanyl)propan-2-ols (R)-(+)-4a-c. All of the investigated yeast strains displayed a very high activity toward prochiral ketones 3a-c converting them to the desired alcohols after relatively short reaction time (1-3.5 h). The biotransformation products were isolated with moderate to good yields (45-89%) and in highly enantioenriched forms (94-99% ee). Stereoselective bioreduction of 1-(1H-benzimidazol-2-ylsulfanyl)propan-2-one 3a by D. hansenii DSM 3428 growing cells provided the respective (R)-alcohol with >99% yield, in reasonable 65% isolated yield and in a highly stereoselective manner (98% ee) after 3 h of cultivation. In the same culture, bioreduction of 1-(1,3-benzoxazol-2-ylsulfanyl)propan-2-one 3b led to a 76% yield, 65% isolated yield and very high 94% ee of the formed (R)-alcohol. Similar 1.5 h incubation of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-one 3c in G. candidum LOCK 105 culture resulted in the corresponding (R)-alcohol preparation in moderate 45% isolated yield with excellent enantiomeric purity (99% ee). (C) 2014 Elsevier B.V. All rights reserved.
• A Powerful Strategy for Synthesizing Block Copolymers via Bimetallic Synergistic Catalysis
  作者：Xiang‐Yu Fu、Tian‐Jun Yue、Bai‐Hao Ren、Hai Wang、Wei‐Min Ren、Xiao‐Bing Lu

  DOI：10.1002/anie.202401926

  日期：2024.4.24

  Block copolymers, comprising polyether and polyolefin segments, are an important and promising category of functional materials. However, the lack of efficient strategies for the construction of polyether‐b‐polyolefin block copolymers have hindered the development of these materials. Herein, we propose a simple and efficient method to obtain various block copolymers through the copolymerization of epoxides and acrylates via bimetallic synergistic catalysis. The copolymerization of epoxides and acrylates proceeds in a sequence‐controlled manner, where the epoxides‐involved homo‐ or copolymerization occurs first, followed by the homopolymerization of acrylates initiated by the alkoxide species from the propagating polymer chain, thus yielding copolymers with a block structure. Notably, the high monomer compatibility of this powerful strategy provides a platform for synthesizing various polyacrylate‐based block copolymers comprising polyether, polycarbonate, polythiocarbonate, polyester, and polyurethane segments, respectively.
• Lipase-catalyzed kinetic resolution of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol with antifungal activity: a comparative study of transesterification versus hydrolysis
  作者：Paweł Borowiecki、Marcin Fabisiak、Zbigniew Ochal

  DOI：10.1016/j.tet.2013.04.014

  日期：2013.6

  A study of chemoenzymatic synthesis of both enantiomers of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol was carried out. Several commercially available lipase preparations were tested as biocatalysts in the kinetic resolution process of target compound by enantioselective transesterification and/or hydrolysis. CAL-B (Novozym 435) was found to be the optimal catalyst. The lipase-mediated hydrolysis approach appeared to be superior to the transesterification reaction. Absolute configuration of the obtained alcohol was postulated, applying modified Mosher's methodology. The inhibitory activity of the synthesized benzothiazole derivatives against pathogenic fungi was checked. (C) 2013 Elsevier Ltd. All rights reserved.