1-(benzothiazol-2-ylsulfanyl)-3-aminopropan-2-ol | 285566-78-1

• 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-(benzothiazol-2-ylsulfanyl)-3-aminopropan-2-ol
• 英文别名: 1-Amino-3-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol
• CAS: 285566-78-1
• 化学式: C₁₀H₁₂N₂OS₂
• 分子量: 240.35
• InChiKey: OZSIACUCHVTEGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙酮 、 1-(benzothiazol-2-ylsulfanyl)-3-aminopropan-2-ol 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以65%的产率得到1-(benzothiazol-2-ylsulfanyl)-3-N-isopropylaminopropan-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：

  1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol 在 一水合肼 、 溶剂黄146 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 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

文献信息

• Synthesis of a series of sulfinic acid analogs of GABA and evaluation of their GABAB receptor affinities
  作者：Nicholas I. Carruthers、James M. Spitler、Shing-Chun Wong、David J. Blythin、Xiao Chen、Ho-Jane Shue、Hoyan S. She、Joe F. Lee、Charles Rizzo、Pauline C. Ting、Robert E. West

  DOI：10.1016/s0960-894x(98)00565-4

  日期：1998.11

  A series of gamma-aminobutyric acid (GABA) I analogs was prepared in which the carboxylic acid group of GABA was replaced with a sulfinic acid group and their affinity for the GABAB receptor investigated. (C) 1998 Elsevier Science Ltd. All rights reserved.
• US4873346A
  申请人：——

  公开号：US4873346A

  公开（公告）日：1989-10-10
• 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.