6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester | 91618-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
• 英文别名: diphenylmethyl (3S,5R,6S)-6-bromo-6-[1'(R)-hydroxyethyl]penicillanate；diphenylmethyl (1'R,3S,5R,6S)-6-bromo-6-(1'-hydroxyethyl)penicillanate；benzhydryl (2S,5R,6S)-6-bromo-6-[(1R)-1-hydroxyethyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 91618-40-5
• 化学式: C₂₃H₂₄BrNO₄S
• 分子量: 490.418
• InChiKey: KOBRBUKXDYDXQY-VSLYICBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester 在 重铬酸吡啶 、 molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以74%的产率得到6β-acetyl-6α-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of 6-bromo-6-substituted penicillanic acid derivatives as β-lactamase inhibitors

  摘要：

  The synthesis of a selected set of 6-bromopenicillanic acid derivatives with an additional C6 substituent is reported. All these substances were tested as inhibitors of class A and C beta-lactamase enzymes derived from Escherichia coli (TEM-1) and E. cloacae (P99). As 6-(1-hydroxyethyl) derivatives 4c and 6c were found to be weak beta-lactamase inhibitors, they were further investigated in combination with amoxicillin against a series of beta-lactamase-producing bacterial strains. Some structure-activity relationships are discussed. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01261-2
• 作为产物：
  描述：

  diphenylmethyl 6,6-dibromopenicillanate 生成 6α-bromo-6β-(1-hydroxyethyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Electrooxidative Desulfurization/Chlorination. A Facile Synthesis of 4-Chloro-2-azetidinones, a Potent Intermediate for Carbapenems
  作者：Hideo Tanaka、Manabu Kuroboshi、Masayoshi Miyada、Syoichi Tateyama

  DOI：10.3987/com-08-s(n)110

  日期：——
• Diastereoselective Synthesis of 6-Bromo-6-(1-hydroxyethyl)penicillanate by Cross-Coupling of 6,6-Dibromopenicillanate and Acetaldehyde Promoted with Grignard Reagents: Role of Amine Ligands
  作者：Hideo Tanaka、Manabu Kuroboshi、Keiko Mesaki、Syoichi Tateyama

  DOI：10.3987/com-07-s(u)47

  日期：——
• ——
  作者：ALPEGIANI M.、 BEDESCHI A.、 FOGLIO M.、 FRANCESCHI G.、 PERRONE E.

  DOI：——

  日期：——
• Synthesis and biological evaluation of 6-bromo-6-substituted penicillanic acid derivatives as β-lactamase inhibitors
  作者：A Bedini、C Balsamini、B Di Giacomo、A Tontini、B Citterio、L Giorgi、E Di Modugno、G Tarzia

  DOI：10.1016/s0014-827x(02)01261-2

  日期：2002.7

  The synthesis of a selected set of 6-bromopenicillanic acid derivatives with an additional C6 substituent is reported. All these substances were tested as inhibitors of class A and C beta-lactamase enzymes derived from Escherichia coli (TEM-1) and E. cloacae (P99). As 6-(1-hydroxyethyl) derivatives 4c and 6c were found to be weak beta-lactamase inhibitors, they were further investigated in combination with amoxicillin against a series of beta-lactamase-producing bacterial strains. Some structure-activity relationships are discussed. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.