(2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-6-[1-phenyl-meth-(E)-ylidene]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester | 667888-91-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-6-[1-phenyl-meth-(E)-ylidene]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester
• CAS: 667888-91-7
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: WRLHHMUZLJLBPE-OABZQCHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-巯基苯并噻唑 、 (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-6-[1-phenyl-meth-(E)-ylidene]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester 以14%的产率得到(R)-2-{(R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-[1-phenyl-meth-(E)-ylidene]-azetidin-1-yl}-3-methyl-but-3-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones

  摘要：

  6-Alkylidenepenicillanate sulfoxides and sulfones were synthesized on the base of 6-oxopenicillanate esters. The targeted splitting of their thiazolidine ring led to the formation of 3-alkylidene substituted 4-heteryldithio and 4-methylsulfonyl azetidin-2-ones. Some of mono and bicyclic beta-lactams revealed potent cytotoxic properties towards monolayer tumor cells in < 10-muM concentrations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.078
• 作为产物：
  描述：

  6-oxopenicillanic acid tert-butyl ester 在 间氯过氧苯甲酸 作用下， 生成 (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-6-[1-phenyl-meth-(E)-ylidene]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones

  摘要：

  6-Alkylidenepenicillanate sulfoxides and sulfones were synthesized on the base of 6-oxopenicillanate esters. The targeted splitting of their thiazolidine ring led to the formation of 3-alkylidene substituted 4-heteryldithio and 4-methylsulfonyl azetidin-2-ones. Some of mono and bicyclic beta-lactams revealed potent cytotoxic properties towards monolayer tumor cells in < 10-muM concentrations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.078