(+/-)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol | 75235-71-1

• 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: (+/-)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol
• 英文别名: 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol；2-benzothiazol-2-ylthio-1-methylethanol；1-benzothiazol-2-ylsulfanyl-propan-2-ol；2-(2-Hydroxy-propylmercapto)-benzthiazol；2-(2-Hydroxy-1-propylthio)benzothiazol；2-Propanol, 1-(2-benzothiazolylthio)-
• CAS: 75235-71-1
• 化学式: C₁₀H₁₁NOS₂
• 分子量: 225.335
• InChiKey: NPVCYDIKUKFSOH-UHFFFAOYSA-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

• 作为反应物：
  描述：

  (+/-)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol 在 氢溴酸 作用下， 反应 12.0h， 生成 2-(2-Brom-propylmercapto)benzthiazol
  参考文献：
  名称：

  Kuznetsova,E.A. et al., Journal of Organic Chemistry USSR (English Translation), 1965, vol. 1, p. 769 - 773

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-苯并噻唑基硫代)-2-丙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到(+/-)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol
  参考文献：
  名称：

  Asymmetric reduction of 1-(benzoazol-2-ylsulfanyl)propan-2-ones using whole cells of Mortierella isabellina, Debaryomyces hansenii, Geotrichum candidum and Zygosaccharomyces rouxii

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2014.07.015

文献信息

• 羟烷基化杂环硼酸酯及其制备方法、用途
  申请人：上海交通大学

  公开号：CN103601748B

  公开（公告）日：2016-11-02

  本发明涉及一种羟烷基化杂环硼酸酯及其制备方法、用途；所述添加剂的结构式如式（I）或（II）所示；本发明还涉及前述的羟烷基化杂环硼酸酯润滑添加剂的制备方法，所述方法包括如下步骤：步骤一，在有机溶剂和催化剂的条件下，杂环化合物和烷基环氧化物反应，生成化合物A；步骤二，在有机溶剂和催化剂的条件下，化合物B与化合物A、或含杂环醇进行反应，即可；本发明还涉及前述羟烷基化杂环硼酸酯的用途。
• 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.
• 1-(1,3-Benzothiazol-2-ylsulfanyl)propan-2-olate anion as a potential multifunctional ligand in aluminum complexes
  作者：Dariusz Basiak、Zbigniew Ochal、Iwona Justyniak、Wanda Ziemkowska

  DOI：10.1016/j.poly.2015.10.048

  日期：2015.12

  1-(1,3-Benzothiazol-2-ylsulfanyl)propan-2-ol (C10H10NS2OH, LH) was used as a multifunctional ligand in reactions with aluminum trialkyls R3Al (R = Bu-i, Et, Bu-t). The reactions at 1:1 M ratio of reagents proceeded with formation of dimeric (R2AlL)(2) (R = Bu-i, Et) complexes with a central Al2O2 ring, whereas in a presence of an excess of R3Al the compounds [(R2Al)(R3Al)L](2) (R = Bu-i, Et) with the central Al2O2 ring and R3Al molecules coordinated to nitrogen atoms were obtained. (Bu3Al)-Bu-i reacted with the LH yielding monomeric complex (Bu2AlL)-Bu-t independently on the molar ratio of reagents. In the compound, Al coordinates to the nitrogen atom to form intramolecular sp(2)-N donor bonding. The compounds [((Bu2Al)-Bu-i)((Bu3Al)-Bu-i)L](2) (1), (Et2AlL)(2) (2) and (Bu2AlL)-Bu-t (3) were synthesized as pure compounds and characterized. Among four heteroatoms of the ligand, only the oxygen and nitrogen atoms can form bonds with aluminum atoms, whereas two sulfur atoms are non-coordinative. The compounds 1 and 2 are active as an initiator of the e-caprolactone polymerization. (C) 2015 Elsevier Ltd. All rights reserved.
• Thermal Reactions of β-Hydroxysulfides Bearing Benzothiazole: Sulfenic Acid Trapping via a Spiro Intermediate
  作者：Nobuhiko Yamada、Takanori Koyasu、Mayumi Sonami、Michiko Aoi、Shintaro Tashiro、Md. Chanmiya Sheikh、Yusuke Ishida、Wataru Kawashima、Toshiaki Yoshimura、Hiroyuki Morita

  DOI：10.1080/10426501003773480

  日期：2010.5.27

  Benzothiazolyl 2-hydroxyethyl sulfoxide (1a) was found to afford bis[2-(2-oxobenzotiazolyl)-ethyl] disulfide (2a) in the presence of DBU at rt. 2a was formed by the condensation of corresponding sulfenic acid intermediate. Thermolyses of 1a in the presence of ethyl propiolate at 60-140 degrees C were carried out to succeed to trap sulfenic acid 6a as an intermediate. Trapping of 2-benzothiazolyloxyenthanesulfenic acid (6a) revealed that the thermal reaction proceeded via a five-membered spiro intermediate 5a.
• REACTION PRODUCTS OF MERCAPTOBENZOTHIAZOLES, MERCAPTOTHIAZOLINES, AND MERCAPTOBENZIMIDAZOLES WITH EPOXIDES AS LUBRICANT ADDITIVES
  申请人：Rowland Robert G.

  公开号：US20090076279A1

  公开（公告）日：2009-03-19

  A composition comprising: (A) a lubricant, and (B) at least one alcohol that is the reaction product of mercaptobenzothiazoles, mercaptothiazolines, or mercaptobenzimidazoles with various epoxies.