2,3,3-tribromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester | 161863-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 2,3,3-tribromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester
• 英文别名: benzyl 3-methyl-2-(2,3,3-tribromo-4-oxoazetidin-1-yl)but-2-enoate
• CAS: 161863-51-0
• 化学式: C₁₅H₁₄Br₃NO₃
• 分子量: 495.993
• InChiKey: QUZLLXFGSXDHHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,3-tribromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester 在 盐酸 、 三氯化铝 、 sodium chloride 作用下， 以 二氯甲烷 、 氮气 、 乙酸乙酯 、 苯甲醚 为溶剂， 生成 2,3,3-tribromo-alpha-(1-methyl-ethylidene)-4-oxo-1-azetidine acetic acid
  参考文献：
  名称：

  2-Bromo- and 2-nitroxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo-azetidines, processes for the preparation thereof and use thereof

  摘要：

  公开号：

  EP0633247B1
• 作为产物：
  描述：

  3,3-dibromo-alpha-(1-methylethylidene)-2-[(5-methyl-isoxazole-3-yl)-aminosulfinyl]-4-oxo-1-azetidine acetic acid benzyl ester 以 氯仿 为溶剂， 以47.6%的产率得到2,3,3-tribromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester
  参考文献：
  名称：

  Novel derivatives of 3-bromo and 3,3-dibromo-4-oxo-1-azetidines, processes for the preparation thereof and their use

  摘要：

  本发明涉及一般式I的3-溴和3,3-二溴-4-氧代-1-氮杂环的衍生物，以及其制备和使用的方法。其中R4为氢、甲基、苄基或其他保护基，R5为氢、烷基、烷基芳基、杂环环，Y为卤素原子，X为卤素原子、烷氧基、亚硝氧基。根据本发明，3-溴和3,3-二溴-4-氧代-1-氮杂环的衍生物通过2-亚磺酸基衍生物的反应制备，优选为4-氧代-氮杂环的2-取代亚磺酰胺，与各种卤代试剂反应后，处理反应混合物，分离出3-溴和3,3-二溴-4-氧代-1-氮杂环的2-卤代衍生物，并与四氟硼酸银和醇反应，得到相应的3-溴和3,3-二溴-4-氧代氮杂环的2-烷氧基衍生物，或将3-溴和3,3-二溴-4-氧代氮杂环的2-卤代衍生物与2-丙醇中的硝酸银反应，处理反应混合物后，得到3-溴和3,3-二溴-4-氧代-1-氮杂环的2-亚硝氧基衍生物。一些新制备的化合物被去保护，得到具有自由羧基的衍生物。制备的化合物是制备抗菌或抗肿瘤治疗的药物组分。

  公开号：

  EP0791580A2

文献信息

• Derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, processes
  申请人：PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija,

  公开号：US05843939A1

  公开（公告）日：1998-12-01

  3-Bromo- and 3,3-dibromo-4-oxo-1-azetidines of the formula I ##STR1## wherein R.sub.1 is hydrogen or bromo, R.sub.2 is hydrogen or bromo, R.sub.3 is hydrogen, ##STR2## wherein R.sub.4 is hydrogen, methyl, benzyl or some other protective group, R.sub.5 is hydrogen, alkyl, alkylaryl, a heterocyclic ring, Y is a halo atom, X is a halo atom, alkoxy group, nitroxy group are provided along with processes for the preparation thereof and the use thereof. The 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines can be prepared by reacting 2-sulfinic acid derivatives, with various halogenating agents, and after treating the reaction mixture, 2-halo derivatives of 3-bromo- and 2,2-dibromo-4-oxo-azetidines are isolated and are subjected to a reaction with silver tetrafluoroborate and alcohols to give the corresponding 2-alkoxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo azetidines, or 2-halo derivatives of 3-bromo- and 3-3-dibromo-4-oxo azetidines are subjected to a reaction with silver nitrate in 2-propanol to give, after treating the reaction mixture, 2-nitroxy derivatives of 3-bromo and 3,3-dibromo-4-oxo-1-azetidines. Some newly prepared compounds are deprotected and derivatives having a free carboxy group are obtained. The prepared compounds are components in pharmaceutical compositions effective in antibacterial or antirumour therapy.

  提供了公式I的3-溴和3,3-二溴-4-氧代-1-氮杂环化合物，其中R.sub.1为氢或溴，R.sub.2为氢或溴，R.sub.3为氢，其中R.sub.4为氢，甲基，苄基或其他保护基，R.sub.5为氢，烷基，烷基芳基，杂环环，Y为卤素原子，X为卤素原子，烷氧基，硝氧基。提供了制备这些化合物的方法和用途。3-溴和3,3-二溴-4-氧代-1-氮杂环可以通过将2-亚磺酸衍生物与各种卤化试剂反应，并在处理反应混合物后，分离出3-溴和2,2-二溴-4-氧代-1-氮杂环的2-卤代衍生物，并使其与四氟硼酸银和醇反应，以给出相应的3-溴和3,3-二溴-4-氧代-1-氮杂环的2-烷氧基衍生物，或将3-溴和3,3-二溴-4-氧代-1-氮杂环的2-卤代衍生物与2-丙醇中的硝酸银反应，处理反应混合物后，得到3-溴和3,3-二溴-4-氧代-1-氮杂环的2-硝氧基衍生物。一些新制备的化合物被去保护，得到具有自由羧基的衍生物。制备的化合物是抗菌或抗肿瘤治疗中有效的药物组分。
• Preparations containing 2-bromo- and 2-nitroxy derivatives of 3-bromo-
  申请人：PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija,

  公开号：US05637581A1

  公开（公告）日：1997-06-10

  Formulations exhibiting antibacterial inhibitory or antitumor action containing an effective amount of 2-bromo-and 2-nitroxy derivatives of 3-bromo and 3,3-dibromo-4-oxo-azetidine, and a method of use of the formulations are provided.

  提供了含有有效量2-溴和2-硝基衍生物的配方，这些衍生物具有抗菌抑制或抗肿瘤作用，这些衍生物是3-溴和3,3-二溴-4-氧代氮杂环丙烷的衍生物，并提供了使用这些配方的方法。
• Novel derivatives of 3-bromo and 3,3-dibromo-4-oxo-1-azetidines, processes for the preparation thereof and their use
  申请人：PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija dionicko drustvo

  公开号：EP0791580A2

  公开（公告）日：1997-08-27

  The invention relates to derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines of general formula I to processes for the preparation thereof and the use thereof. wherein wherein R4 is hydrogen, methyl, benzyl or some other protective group, R5 is hydrogen, alkyl, alkylaryl, a heterocyclic ring, Y is halo atom, X is halo atom, alkoxy group, nitroxy group. According to the invention derivatives of 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines are prepared by the reaction of 2-sulfinic acid derivatives, preferably 2-substituted sulfinamides of 4-oxo-azetidines with various halogenating agents, and after the treatment of the reaction mixture, 2-halo derivatives of 3-bromo- and 3,3-dibromo-4-oxo-azetidines are isolated and are subjected to a reaction with silver tetrafluoroborate and alcohols to give the corresponding 2-alkoxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo azetidines, or 2-halo derivatives of 3-bromo- and 3,3-dibromo-4-oxo azetidines are subjected to a reaction with silver nitrate in 2-propanol to give, after the treatment of the reaction mixture, 2-nitroxy derivatives of 3-bromo and 3,3-dibromo-4-oxo-1-azetidines. Some newly prepared compounds are deprotected and derivatives having a free carboxy group are obtained. The prepared compounds are components in pharmaceutical compositions effective in antibacterial or antitumour therapy.

  本发明涉及一般式I的3-溴和3,3-二溴-4-氧代-1-氮杂环的衍生物，以及其制备和使用的方法。其中R4为氢、甲基、苄基或其他保护基，R5为氢、烷基、烷基芳基、杂环环，Y为卤素原子，X为卤素原子、烷氧基、亚硝氧基。根据本发明，3-溴和3,3-二溴-4-氧代-1-氮杂环的衍生物通过2-亚磺酸基衍生物的反应制备，优选为4-氧代-氮杂环的2-取代亚磺酰胺，与各种卤代试剂反应后，处理反应混合物，分离出3-溴和3,3-二溴-4-氧代-1-氮杂环的2-卤代衍生物，并与四氟硼酸银和醇反应，得到相应的3-溴和3,3-二溴-4-氧代氮杂环的2-烷氧基衍生物，或将3-溴和3,3-二溴-4-氧代氮杂环的2-卤代衍生物与2-丙醇中的硝酸银反应，处理反应混合物后，得到3-溴和3,3-二溴-4-氧代-1-氮杂环的2-亚硝氧基衍生物。一些新制备的化合物被去保护，得到具有自由羧基的衍生物。制备的化合物是制备抗菌或抗肿瘤治疗的药物组分。
• US5637581A
  申请人：——

  公开号：US5637581A

  公开（公告）日：1997-06-10
• US5670638A
  申请人：——

  公开号：US5670638A

  公开（公告）日：1997-09-23