6-diazopenicillanic acid benzyl ester | 15058-70-5

• 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: 6-diazopenicillanic acid benzyl ester
• 英文别名: 6-Diazo-penicillansaeure-benzylester；benzyl 6-diazapenicillanate；benzyl 6-diazopenicillanate；benzyl (2S,5R,6E)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 15058-70-5
• 化学式: C₁₅H₁₅N₃O₃S
• 分子量: 317.368
• InChiKey: OBFYUBPPQSHWQX-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-diazopenicillanic acid benzyl ester 在 溴 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl 6,6-dibromopenicillanate
  参考文献：
  名称：

  6-Substituted methyl penicillins, derivatives and analogues thereof

  摘要：

  揭示了抗生素6-(取代甲基) 青霉素、其衍生物和核类似物；其中甲基取代物包括羟基、酮氧、亚胺氮、氨基或硫。还披露了制备这类化合物及其药用盐、酯和酰胺衍生物的方法；包含这类化合物的药物组合物；以及在需要抗生素效果时，通过给予这类化合物和组合物进行治疗的方法。

  公开号：

  US04207323A1
• 作为产物：
  描述：

  penicillin G benzyl ester 在 sodium acetate 、 dinitrogen tetraoxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-diazopenicillanic acid benzyl ester
  参考文献：
  名称：

  Giddings, Peter J.; John, D. Ivor; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1982, # 11, p. 2757 - 2766

  摘要：

  DOI：

文献信息

• 6.alpha., .beta.-Substituted penicillin derivatives
  申请人：Merck & Co., Inc.

  公开号：US04035359A1

  公开（公告）日：1977-07-12

  Novel 6-methoxy and 6-thioalkyl-6-acylamido-penicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.

  新型的6-甲氧基和6-硫代烷基-6-酰胺基-青霉烷酸及其无毒的药用可接受盐、酯和酰胺，可用作抗生素。这些产品是通过将6-取代-6-氨基青霉烷酸酯与酰化剂处理后去除酯基而制备的。还披露了新型中间体。
• Preparation and reduction of 6-phenylselenylpenicillanates. A stereoselective synthesis of 6β-substituted penicillanates
  作者：Peter J. Giddings、Ivor John D、Eric J. Thomas

  DOI：10.1016/s0040-4039(01)85484-8

  日期：1980.1

  The preparation and tri-n-butyltin hydride reduction of benzyl 6-chloro-6-phenyl-selenyl- and benzyl 6,6-bis(phenylselenyl)penicillanates, and related compounds, is discussed.

  讨论了苄基6-氯-6-苯基-硒基苯甲酸和苄基6,6-双（苯基硒基）青霉酸酯的制备和氢化三正丁基锡以及相关化合物。
• Derivatives of 6-aminopenicillanic acid
  申请人：Merck & Co., Inc.

  公开号：US04071529A1

  公开（公告）日：1978-01-31

  Novel 6-methoxy and 6-thioalkyl-6-acylamidopenicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.

  新型的6-甲氧基和6-硫代烷基-6-酰胺基青霉烷酸及其无毒的药用可接受盐、酯和酰胺，可用作抗生素。这些产品是通过将6-取代-6-氨基青霉烷酸酯与酰化剂处理，然后去除酯基而制备的。还披露了新型中间体。
• 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。