1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-one | 285566-73-6

• 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-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-one
• 英文别名: 1-Chloro-3-(2-benzthiazolylthio)-2-propanone；1-(1,3-benzothiazol-2-ylsulfanyl)-3-chloropropan-2-one
• CAS: 285566-73-6
• 化学式: C₁₀H₈ClNOS₂
• 分子量: 257.765
• InChiKey: TYPJRQNEJCSOEG-UHFFFAOYSA-N

物化性质

• 沸点：
  394.3±48.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-one 在 sodium tetrahydroborate 、 一水合肼 、 溶剂黄146 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 1-(benzothiazol-2-ylsulfanyl)-3-aminopropan-2-ol
  参考文献：
  名称：

  Chemical and chemoenzymatic routes to 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol, a precursor of drugs with potential β-blocker activity

  摘要：

  Several methods have been developed to prepare 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol 2 with good to high enantiomeric excess: 70 and 93% ees have in fact been obtained by baker's yeast-induced asymmetric reduction of the ketone precursor 1 and by kinetic resolution performed in the presence of lipase from Pseudomonas sp. (E = 38), respectively. Compounds (R)-(+)-2 and (S)-(-)-2 have also been prepared by a chemical method in 90% yield and with enantiomeric excesses of 98 and 96.4%, respectively. HPLC on Chiralcel OD column separation of enantiomers (separability factor alpha = 1.64) has also been successfully performed. Compound 2 could, in turn, be used for the synthesis in an optically active form of various molecules, including beta-aminoalcohols 6, drugs with potential beta-blocker activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00102-6
• 作为产物：
  描述：

  2-巯基苯并噻唑 、 1,3-二氯丙酮 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以46%的产率得到1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-one
  参考文献：
  名称：

  Chemical and chemoenzymatic routes to 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol, a precursor of drugs with potential β-blocker activity

  摘要：

  Several methods have been developed to prepare 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol 2 with good to high enantiomeric excess: 70 and 93% ees have in fact been obtained by baker's yeast-induced asymmetric reduction of the ketone precursor 1 and by kinetic resolution performed in the presence of lipase from Pseudomonas sp. (E = 38), respectively. Compounds (R)-(+)-2 and (S)-(-)-2 have also been prepared by a chemical method in 90% yield and with enantiomeric excesses of 98 and 96.4%, respectively. HPLC on Chiralcel OD column separation of enantiomers (separability factor alpha = 1.64) has also been successfully performed. Compound 2 could, in turn, be used for the synthesis in an optically active form of various molecules, including beta-aminoalcohols 6, drugs with potential beta-blocker activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00102-6

文献信息

• Chemical and chemoenzymatic routes to 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol, a precursor of drugs with potential β-blocker activity
  作者：Leonardo Di Nunno、Carlo Franchini、Antonio Scilimati、Maria Stefania Sinicropi、Paolo Tortorella

  DOI：10.1016/s0957-4166(00)00102-6

  日期：2000.4

  Several methods have been developed to prepare 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol 2 with good to high enantiomeric excess: 70 and 93% ees have in fact been obtained by baker's yeast-induced asymmetric reduction of the ketone precursor 1 and by kinetic resolution performed in the presence of lipase from Pseudomonas sp. (E = 38), respectively. Compounds (R)-(+)-2 and (S)-(-)-2 have also been prepared by a chemical method in 90% yield and with enantiomeric excesses of 98 and 96.4%, respectively. HPLC on Chiralcel OD column separation of enantiomers (separability factor alpha = 1.64) has also been successfully performed. Compound 2 could, in turn, be used for the synthesis in an optically active form of various molecules, including beta-aminoalcohols 6, drugs with potential beta-blocker activity. (C) 2000 Elsevier Science Ltd. All rights reserved.