(pivaloyloxy)methyl 6β-bromopenicillanate | 74772-33-1

• 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: (pivaloyloxy)methyl 6β-bromopenicillanate
• 英文别名: Pivaloyloxymethyl 6-β-Bromopenicillanate；pivaloyloxymethyl 6β-bromopenicillanate；pivaloyloxymethyl 6-beta-bromopenicillanate；2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 74772-33-1
• 化学式: C₁₄H₂₀BrNO₅S
• 分子量: 394.287
• InChiKey: YAEDTOVMUNTASW-KHQFGBGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (pivaloyloxy)methyl 6β-bromopenicillanate 以75%的产率得到
  参考文献：
  名称：

  SOMOZA, CARMEN;MASCARETTI, ORESTE A., TETRAHEDRON, 44,(1988) N 23, C. 7007-7012

  摘要：

  DOI：
• 作为产物：
  描述：

  (pivaloyloxy)methyl 6α-<(fluorosulfonyl)oxy>penicillinate 在 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以95%的产率得到(pivaloyloxy)methyl 6β-bromopenicillanate
  参考文献：
  名称：

  Nucleophilic SN2 displacements on (pivaloyloxy)methyl 6.alpha.-[(fluorosulfonyl)oxy]penicillanate

  摘要：

  DOI：

  10.1021/jo00366a032

文献信息

• 6-.beta.-substituted penicillanic acid compound free of the
  申请人：Pfizer Inc.

  公开号：US04656263A1

  公开（公告）日：1987-04-07

  6-.beta.-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria, and 6-.beta.-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-.beta.-substituted penicillanic acid congeners.

  6-β-取代青霉烷酸及其衍生物作为增强多种β-内酰胺酶产生细菌对多种β-内酰胺类抗生素有效性的有用增效剂，以及6-β-取代青霉烷酸衍生物，其中羧基被传统的青霉素羧基保护基团所保护，作为导致所述协同作用剂的有用中间体。一种将6,6-二取代青霉烷酸衍生物转化为相应的6-β-取代青霉烷酸同系物的方法。
• Process for converting 6,6-disubstituted penicillanic acid derivatives
  申请人：Pfizer Inc.

  公开号：US04397783A1

  公开（公告）日：1983-08-09

  6-.beta.-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria, and 6-.beta.-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-.beta.-substituted penicillanic acid congeners.

  6-β-取代青霉烷酸及其衍生物作为增强多种β-内酰胺酶产生细菌对多种β-内酰胺类抗生素有效性的有用增效剂，以及6-β-取代青霉烷酸衍生物，其中羧基被传统的青霉素羧基保护基团所保护，作为导致所述协同作用剂的有用中间体。一种将6,6-二取代青霉烷酸衍生物转化为相应的6-β-取代青霉烷酸同系物的方法。
• 6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
  申请人：Pfizer Inc.

  公开号：US04432970A1

  公开（公告）日：1984-02-21

  6-beta-Halopenicillanic acid 1,1-dioxides, physiologically acceptable salts thereof and esters thereof readily hydrolyzable; pharmaceutical compositions containing a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable; and a method for enhancing the effectiveness of a beta-lactam antibiotic, using a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable.

  6-β-卤代苯乙酸1,1-二氧化物，其生理可接受盐及其易于水解的酯；含有6-β-卤代苯乙酸1,1-二氧化物，其生理可接受盐或其易于水解的酯的药物组合物；以及使用6-β-卤代苯乙酸1,1-二氧化物，其生理可接受的盐或易于水解的酯来增强β-内酰胺抗生素效果的方法。
• Derivatives of penicillanic acid
  申请人：Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik

  公开号：US04446144A1

  公开（公告）日：1984-05-01

  This invention relates to penicillanic acid derivatives of the formula I ##STR1## in which X stands for chlorine, bromine or iodine, to pharmaceutically acceptable, non-toxic salts of the compounds of formula I, to pharmaceutically acceptable, easily hydrolyzable esters thereof, including salts of such esters, to pharmaceutical compositions containing the compounds of the invention and dosage units thereof, to methods for the preparation of the compounds of the invention, and to methods of using the said new compounds in the human and veterinary therapy. The 6.beta.-halopenicillanic acids of formula I are potent inhibitors of .beta.-lactamases from a variety of gram-positive and gram-negative bacteria, making the 6.beta.-halopenicillanic acids as well as their salts and easily hydrolyzable esters valuable in human and veterinary medicine.

  本发明涉及公式I的青霉酸衍生物，其中X代表氯、溴或碘，以及公式I化合物的药学上可接受的、无毒的盐，其易水解的酯，包括这些酯的盐，含有该发明化合物的药物组合物和其剂量单位，制备该发明化合物的方法，以及在人类和兽医治疗中使用这些新化合物的方法。公式I的6-β-卤代青霉酸是多种革兰氏阳性和阴性细菌β-内酰胺酶的强效抑制剂，使得6-β-卤代青霉酸及其盐和易水解的酯在人类和兽医医学中具有重要价值。
• Synthesis of optically active (pivaloyloxy)methyl 2',3'-substituted 4'-oxoazetidin-1'-yl-3-methylbut-2-enoates from 6-apa
  作者：Carmen Somoza、Oreste A. Mascaretti

  DOI：10.1016/s0040-4020(01)86069-5

  日期：1988.1

  The title compound were prepared as useful optically active intermediates for the synthesis of “non-classical” β-lactam compounds. These monocyclic azetidinones were formed by cleavage of sulfur-carbon 5 bond of bicyclic penicillanates with chlorine or tert-butyl hypochlorite in appropiate solvents.

  将标题化合物制备为有用的旋光中间体，用于合成“非经典”β-内酰胺化合物。这些单环氮杂环丁酮是通过在适当的溶剂中用氯或次氯酸叔丁酯裂解双环青酸酯的硫碳5键形成的。