tert-butyl (2S,5R,6Z)-3,3-dimethyl-6-[(4-nitrophenyl)methylidene]-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | 667888-94-0

• 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: tert-butyl (2S,5R,6Z)-3,3-dimethyl-6-[(4-nitrophenyl)methylidene]-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• 英文别名: tert-butyl (2S,5R,6Z)-3,3-dimethyl-6-[(4-nitrophenyl)methylidene]-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 667888-94-0
• 化学式: C₁₉H₂₂N₂O₇S
• 分子量: 422.459
• InChiKey: FRRUYGOWVIUKOE-PXXUHZIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,5R,6Z)-3,3-dimethyl-6-[(4-nitrophenyl)methylidene]-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 在 三氟乙酸 作用下， 以70%的产率得到(2S,5R,6Z)-3,3-dimethyl-6-[(4-nitrophenyl)methylidene]-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  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：

  (4-nitrobenzylidene)triphenylphosphorane 在 间氯过氧苯甲酸 作用下， 生成 tert-butyl (2S,5R,6Z)-3,3-dimethyl-6-[(4-nitrophenyl)methylidene]-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  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

文献信息

• Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones
  作者：Grigory Veinberg、Irina Shestakova、Maxim Vorona、Iveta Kanepe、Edmunds Lukevics

  DOI：10.1016/j.bmcl.2003.09.078

  日期：2004.1

  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.