6β-bromopenicillanic acid benzyl ester | 71840-49-8

• 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: 6β-bromopenicillanic acid benzyl ester
• 英文别名: benzyl 6β-bromopenicillanate；benzyl (2S,5R,6R)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 71840-49-8
• 化学式: C₁₅H₁₆BrNO₃S
• 分子量: 370.267
• InChiKey: YNUFZPPJOZEBQK-NTZNESFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 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：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6β-bromopenicillanic acid benzyl ester 在 potassium permanganate 作用下， 生成 6β-bromopenicillanic acid 1,1-dioxide benzyl ester
  参考文献：
  名称：

  Stereoselective Preparation of 6-b-Bromopenicillanic Acid Derivatives

  摘要：

  A new stereoselective method for the preparation of 6-beta-bromopenicillanates is described. It comprises the reaction of 6,6-dibromopenicillanates with silver nitrate in 2-propanol.

  DOI：

  10.3987/com-94-6898
• 作为产物：
  描述：

  benzyl 6,6-dibromopenicillanate 在 silver nitrate 作用下， 以 异丙醇 为溶剂， 以89%的产率得到6β-bromopenicillanic acid benzyl ester
  参考文献：
  名称：

  Stereoselective Preparation of 6-b-Bromopenicillanic Acid Derivatives

  摘要：

  A new stereoselective method for the preparation of 6-beta-bromopenicillanates is described. It comprises the reaction of 6,6-dibromopenicillanates with silver nitrate in 2-propanol.

  DOI：

  10.3987/com-94-6898

文献信息

• Stereoselective preparation of 6β -substituted penicillanates
  作者：D.Ivor John、Nicholas D. Tyrrell、Eric J. Thomas

  DOI：10.1016/s0040-4020(01)92141-6

  日期：1983.1

  6β-methoxycarbonylethyl-, 6β-(t-butoxycarbonylmethyl)-, and 6β-methylthiopenicillanates 10–15 have been prepared stereo-selectively by tri-n-butyltin hydride reduction of the corresponding 6β-isocyanopenicillanates 4–9 A minor side-product (15%) isolated from the reduction of benzyl 6α-(2-hydroxyprop-2-yl)-6β-isocyanopenicillanate 5 was identified as (1R, 5R)-6-[(1R)-1-benzyloxycarbonyl-2-methylprop-1

  6β-苄基，6β-（2-羟基丙-2-基） - ，6β甲氧羰基甲基，6β-methoxycarbonylethyl-，6β-（叔丁氧基羰基） - ，和6β-methylthiopenicillanates 10 - 15已经制备立体选择性地通过三-正丁基锡氢化物还原相应的6β-isocyanopenicillanates的4 - 9选自苄基6α-（2-羟基丙-2-基）的还原分离的次要副产物（15％）-6β-isocyanopenicillanate 5被确定as（1R，5R）-6-[（（1R）-1-苄氧羰基-2-甲基丙-1-基] -1-（2-羟基丙-2-基）-2,6-二氮杂-4-硫杂双环[3 ，2,0] hept-2-en-7-one 18和少量类似的噻唑啉19和20从6α-苄基-和6α-甲氧基羰基甲基-6β-异氰基Openicillanates 4和6的还原中检测到粗混合物中的。通过三正丁
• Selective oxidation of penicillin derivatives to penicillin (1R) and (1S)-sulfoxides using dimethyldioxirane
  作者：Gerardo O. Danelon、Ernesto G. Mata、Oreste A. Mascaretti

  DOI：10.1016/s0040-4039(00)61499-5

  日期：1993.12

  6-dihalo-, 6β-halo-penicillanates, 6,6-dihalopenam derivatives and (1S)-6-α-halopenicillanates sulfoxides by dimethyldioxirane asymmetric oxidation of the corresponding penicillanates and penam derivatives. This method is characterized by mild reactions conditions, short reaction times, excellent selectivity, very high yield, ease of reaction workup and complete avoidance of overoxidation products.

  我们描述了通过相应的青霉酸酯和二甲基二环氧乙烷烷不对称氧化制备（1R）-6,6-二卤代-，6β-卤代青霉酸酯，6,6-二卤代戊酰胺衍生物和（1S）-6-α-卤代青酸酯亚砜的便捷程序戊烷衍生物。该方法的特点是反应条件温和，反应时间短，选择性好，产率极高，反应后处理容易并且完全避免了过氧化产物的产生。
• 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。
• Process for debromination of dibromopenicillanic acid and derivatives
  申请人：PFIZER INC.

  公开号：EP0129360A1

  公开（公告）日：1984-12-27

  A process for the debromination of 6-monobromo- and 6,6-dibromopenicillanic acid, and various derivatives thereof, bythe action of a bisulfite salt. The debrominated compounds produced find various utilities, as beta-lactamase inhibitors useful in therapy in combination with known beta-lactam antibiotics, or as intermediates in the further synthesis of useful betalactam compounds.

  一种通过亚硫酸氢盐的作用使 6-单溴和 6,6-二溴青霉烷酸及其各种衍生物脱溴的工艺。生成的脱溴化合物有多种用途，可作为β-内酰胺酶抑制剂与已知的β-内酰胺抗生素联合使用，或作为进一步合成有用的β-内酰胺化合物的中间体。
• 6-(1-Carbamoyl-1-hydroxymethyl)penicillanic-acid derivatives
  申请人：PFIZER INC.

  公开号：EP0220939A1

  公开（公告）日：1987-05-06

  6-(1-Carbamoyl-1-hydroxymethyl)penicillanic acid derivatives of the formula: wherein n is 0, 1 or 2; R is hydrogen, a radical group forming an ester hydrolyzable under physiological conditions, or an acyloxymethyl or 1-(acyloxy)ethyl radical derived from a conventional beta-lactam antibiotic; and R1 and R2 are taken separately and are each independently for example, hydrogen, (C1-C4)alkyl, (C5-C6)cycloalkyl, phenyl benzyl or one of said groups substituted by methyl, hydroxy, (Cl-C2)alkoxy, -COOR3, or -CONR3R4; or R1 and RZ are taken together with the nitrogen to which they are attached to form for example, a pyrrolidine, piperidine, perhydroazepine, morpholine 4-[formyl, (C1-C4)alkyl, phenyl benzyl, pyridyl or 2-hydroxyethyl]piperazine, indoline, isoindoline, 1,2,3,4-tetrahydroquinoline or 1,2,3,4-tetrahydroisoquinoline ring system, or one af said ring systems substituted by methyl, hydroxy, hydroxymethyl, carboxy, carbamoyl, -COOR3 or -CONR3R4. The compounds are useful as antibacterial agents and/or betalactamase inhibitors.

  式中的 6-(1-氨基甲酰基-1-羟甲基)青霉烷酸衍生物： 其中 n 是 0、1 或 2； R 是氢、在生理条件下可水解的形成酯的基团、或来自传统 beta-内酰胺类抗生素的酰氧基甲基或 1-（酰氧基）乙基；以及 R1 和 R2 分别独立地为氢、(C1-C4)烷基、(C5-C6)环烷基、苯基苄基或被甲基、羟基、(Cl-C2)烷氧基、-COOR3 或-CONR3R4 取代的上述基团之一；或 R1 和 RZ 与它们所连接的氮一起形成例如吡咯烷、哌啶、过氢氮杂卓、吗啉 4-[甲酰基、(C1-C4)烷基、苯基苄基、吡啶基或 2-羟乙基]哌嗪、吲哚啉、异吲哚啉、1,2,3,4-四氢喹啉或 1,2,3,4-四氢异喹啉环系，或其中一个被甲基、羟基、羟甲基、羧基、氨基甲酰基、-COOR3 或 -CONR3R4 取代的环系。 这些化合物可用作抗菌剂和/或β-内酰胺酶抑制剂。