6α-bromopenicillanic acid pivalolyloxymethyl ester | 76468-87-6

• 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: 6α-bromopenicillanic acid pivalolyloxymethyl ester
• 英文别名: (pivaloyloxy)methyl 6α-bromo-penicillanate；(pivaloyloxy)methyl 6α-bromopenicillanate；pivaloyloxymethyl 6α-bromopenicillanate；pivaloyloxymethyl 6-alpha-bromopenicillanate；2,2-dimethylpropanoyloxymethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 76468-87-6
• 化学式: C₁₄H₂₀BrNO₅S
• 分子量: 394.287
• InChiKey: YAEDTOVMUNTASW-OYNCUSHFSA-N

物化性质

• 沸点：
  481.0±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

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：

  6α-bromopenicillanic acid pivalolyloxymethyl ester 在 钯 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 舒巴坦匹酯
  参考文献：
  名称：

  6-Alpha-halopenicillanic acid 1,1-dioxides

  摘要：

  一种制备在体内容易水解的青霉烷酸1,1-二氧化物及其酯的方法，包括将6-卤代青霉酸或在体内容易水解的其酯氧化为相应的6-卤代青霉酸1,1-二氧化物或其酯，然后进行去卤代反应（例如氢解）。其中一些在体内容易水解的6-卤代青霉酸1,1-二氧化物及其酯是新颖的中间体。青霉烷酸1,1-二氧化物及其在体内容易水解的酯是已知的化合物，它们是β-内酰胺酶抑制剂，可以增强特定β-内酰胺类抗生素（例如青霉素）在哺乳动物，尤其是人类的细菌感染治疗中的有效性。

  公开号：

  US04420426A1
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 氢溴酸 、 三乙胺 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 生成 6α-bromopenicillanic acid pivalolyloxymethyl ester
  参考文献：
  名称：

  Attachment of a styryl group to the 6-position of a protected penicillanic acid via cobaloxime-mediated radical alkyl-alkenyl cross coupling

  摘要：

  Cobaloxime-catalyzed cross coupling of styrene with 6 alpha-bromopenicillanic acid pivalolyloxymethyl ester (4) introduces a styryl group into the 6 position of the penicillanic acid nucleus. The method should be capable of introducing a variety of aryl-substituted alkenes into the 6 position. Such compounds may be useful as novel beta-lactam antibiotics/beta-lactamase inhibitors. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00415-5

文献信息

• Synthesis of Novel 6-.ALPHA. and 6-.BETA.-Alkylcarbonylmethyl Substituted Penems.
  作者：G. PENTASSUGLIA、G. TARZIA、D. ANDREOTTI、C. BISMARA、R. CARLESSO、D. DONATI、G. GAVIRAGHI、A. PERBONI、A. PEZZOLI、T. ROSSI、B. TAMBURINI、A. URSINI

  DOI：10.7164/antibiotics.48.399

  日期：——

  6-beta Alkylcarbonylmethyl penems were synthesized from 6-alpha-bromo and 6-oxo penicillanates respectively and their in vitro antibacterial activity was studied. The compounds were generally active against Gram-positive but not against Gram-negative strains, the compounds of the 6-beta series being more active. Relatively to imipenem, taken as reference compound, the penems resulted more stable towards

  分别从6-α-溴和6-氧代青霉酸酯合成6-α和6-β烷基羰基甲基青霉烯，并研究了它们的体外抗菌活性。这些化合物通常对革兰氏阳性菌株有活性，但对革兰氏阴性菌株没有活性，6-β系列化合物更具活性。相对于亚胺培南（作为参考化合物），该penems在Tris-HCl缓冲液（pH 7.4）中对化学水解更稳定，但对脱氢肽酶-I（DHP-1）更敏感。
• Improved method for preparing penicillanic acid derivatives
  申请人：Leo Pharmaceutical Products Ltd. A/S

  公开号：US04816580A1

  公开（公告）日：1989-03-28

  The present invention relates to a new process for the debromination and/or deiodination of 6,6-dihalo- and 6-monohalopenicillanic acids or derivatives thereof by treatment with dialkyl, trialkyl or diaralkyl phosphite, the desired compounds being obtained in good to excellent yield and in a high state of purity.

  本发明涉及一种新的工艺，用于通过与二烷基、三烷基或二芳基磷酸酯处理6,6-二卤代和6-单卤代青霉烷酸或其衍生物来进行去溴化和/或去碘化，所得的目标化合物产率良好至极佳，并且具有高纯度。
• 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。
• Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds
  申请人：BEECHAM GROUP PLC

  公开号：EP0013617A1

  公开（公告）日：1980-07-23

  This invention relates to a process for the preparation of certain penicillin derivatives which are useful as β-lactamase inhibitors. The compounds which may be prepared by the process of this invention have formula (I), or a pharmaceutically acceptable salt or ester thereof: wherein R represents hydrogen, halogen, C1-6alkylthio, C1-6alkyl or alkyl substituted with phenyl, carboxy, C1-6alkoxycarbonyl, hydroxyorC1-6alkylthio, and n is zero, 1 or 2. In addition certain of the compounds produced by the process of the invention are novel compounds.

  本发明涉及一种制备某些青霉素衍生物的工艺，这些衍生物可用作β-内酰胺酶抑制剂。可通过本发明工艺制备的化合物具有式（I）或其药学上可接受的盐或酯： 其中R代表氢、卤素、C1-6烷硫基、C1-6烷基或被苯基、羧基、C1-6烷氧基羰基、羟基或C1-6烷硫基取代的烷基，n为0、1或2。此外，本发明工艺生产的某些化合物是新型化合物。
• Beta-lactamase inhibiting 6-(alkoxyaminomethyl)penicillanic acid 1,1-dioxide and derivatives
  申请人：PFIZER INC.

  公开号：EP0128037A1

  公开（公告）日：1984-12-12

  6-alpha/beta-[(C1-C4) Alkoxyaminomethyl and benrylox- yaminomethyl] penicillanic acid 1,1-dioxides, pharmaceutically acceptable salts thereof and conventional esters thereof hydrolyzable under physiological conditions, all of which are useful in medicine as beta-lactamase inhibitors; intermediates and processes therefor; and a process forthe conversion of the present compounds to 6-alpha- and 6-beta-(aminomethyl) penicillanic acid 1,1-dioxides and derivatives.

  6-α-/beta-[(C1-C4)烷氧基氨甲基和苄氧基氨甲基]青霉烷酸 1,1-二氧化物、其药学上可接受的盐及其在生理条件下可水解的常规酯，所有这些化合物都可作为β-内酰胺酶抑制剂用于医药；中间体及其工艺；以及将本化合物转化为 6-α-和 6-beta-（氨甲基）青霉烷酸 1,1-二氧化物及其衍生物的工艺。