1-(1H-benzimidazol-2-ylsulfanyl)propan-2-one | 5268-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(1H-benzimidazol-2-ylsulfanyl)propan-2-one
• 英文别名: 1-(1H-benzoimidazol-2-ylsulfanyl)-propan-2-one；2-(acetylmethylthio)benzimidazole；2-(2-Oxo-propyl-mercapto)-benzimidazol；1-(2-Benzimidazolylthio)-propan-2-on；1-((1H-benzo[d]imidazol-2-yl)thio)propan-2-one
• CAS: 5268-67-7
• 化学式: C₁₀H₁₀N₂OS
• 分子量: 206.268
• InChiKey: QEIAYIODUFAZTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(1H-benzimidazol-2-ylsulfanyl)propan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到1-(1H-benzimidazol-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
• 作为产物：
  描述：

  一氯丙酮 、 1H-苯并咪唑-2-硫醇 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.17h， 以90%的产率得到1-(1H-benzimidazol-2-ylsulfanyl)propan-2-one
  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

• Pyrazolo(1,5-a)benzimidazole couplers
  申请人：Eastman Kodak Company

  公开号：US05210209A1

  公开（公告）日：1993-05-11

  The invention provides a method for the production of a pyrazolo(1,5-a)benzimidazole of the general formula (A): ##STR1## wherein R is a substituted or unsubstituted alkyl or aryl group, and R.sup.1 -R.sup.4 =R, H, halogen, OR, COOR, CONHR, SO.sub.2, NO.sub.2 NHR, NR.sub.2, or CN, and X is hydogen or a reactive group releasable on coupling with an oxidized color developer, wherein the invention provides reacting a 2-amino or 2-mercapto substituted benzimidazole to form a triazepinone or a thiadiazino derivative respectively, ring contracting said triazepinone or thiadiazino derivative to give the corresponding 2-methylpyrazolobenzimidazole product, and subsequently removing the substituents at the -3 or -4 positions to provide a compound of the general formula (1).

  这项发明提供了一种生产嘧唑啉并咪唑（1,5-a）苯并咪唑的方法，其通式为（A）：其中R为取代或未取代的烷基或芳基，R.sup.1-R.sup.4=R，H，卤素，OR，COOR，CONHR，SO.sub.2，NO.sub.2 NHR，NR.sub.2或CN，X为氢或与氧化色发展剂偶联时可释放的活性基团。该发明提供了将2-氨基或2-巯基取代苯并咪唑反应以形成三唑环酮或噻二唑衍生物，分别将该三唑环酮或噻二唑衍生物环收缩以得到相应的2-甲基嘧唑啉并咪唑产物，并随后去除-3或-4位置的取代基，以提供通式（1）的化合物。
• Investigations in the imidazole series
  作者：A. N. Krasovskii、P. M. Kochergin、T. E. Kozlovskaya

  DOI：10.1007/bf00944424

  日期：1971.3
• KRASOVSKIJ O. M., FARMATSEVTICHNIJ ZH., 1980, HO 2, 38-42
  作者：KRASOVSKIJ O. M.

  DOI：——

  日期：——
• KRASOVSKIJ A. N.; KLYUEV N. A.; POMAH A. B.; ZHILNIKOV V. G.; COPOKA I. I+, UKR. XIM. ZH., 1981, 47, HO 2, 189-194
  作者：KRASOVSKIJ A. N.、 KLYUEV N. A.、 POMAH A. B.、 ZHILNIKOV V. G.、 COPOKA I. I+

  DOI：——

  日期：——
• PYRAZOLO(1,5-a)BENZIMIDAZOLE COUPLERS
  申请人：KODAK LIMITED

  公开号：EP0485423A1

  公开（公告）日：1992-05-20