6β-benzylideneamino-penicillanic acid | 21019-16-9

• 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-benzylideneamino-penicillanic acid
• 英文别名: N-Benzylidene-6-Aminopenicillanic Acid；6β-Benzylidenamino-penicillansaeure；(2S,5R,6R)-6-(benzylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 21019-16-9
• 化学式: C₁₅H₁₆N₂O₃S
• 分子量: 304.37
• InChiKey: CSNWCPXOFXWKLL-NTZNESFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6β-benzylideneamino-penicillanic acid 生成 6α-methylsulfanyl-6β-(2-phenyl-acetylamino)-penicillanic acid
  参考文献：
  名称：

  6-甲基硫代青霉素和7-杂原子取代的头孢菌素的合成。

  摘要：

  DOI：

  10.1021/jo00945a023
• 作为产物：
  描述：

  6-aminopenicillanic acid, t-octylamine salt 在 苯甲醛 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6β-benzylideneamino-penicillanic acid
  参考文献：
  名称：

  6-Arylthio penicillanic acid and derivatives thereof

  摘要：

  本文披露了在6位取代的青霉酸及其衍生物，以及制备这些化合物的过程和其用途。本发明的化合物被发现可用作抗菌剂。

  公开号：

  US03965093A1

文献信息

• 1-Oxides of Schiff bases of 6-aminopenicillanic acid
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03994912A1

  公开（公告）日：1976-11-30

  Compounds containing a cephem nucleus are prepared by heating a 1-oxide of a Schiff base of 6-aminopenicillanic acid. These cephem compounds are useful as intermediates in the preparation of physiologically active cephalosporins.

  含有头孢素核的化合物是通过加热6-氨基青霉素酸的Schiff碱的1-氧化物制备的。这些头孢素化合物在制备生理活性头孢菌素中起着中间体的作用。
• Substitution der 6-Aminopenicillansäure am Kohlenstoffatom 6
  作者：R. Reiner、P. Zeller

  DOI：10.1002/hlca.19680510812

  日期：1968.10.31

  AbstractThe hydroxyalkylation of the penicillin nucleus at C‐6 with benzaldehyde and formaldehyde is reported. 6‐aminopenicillanic acid (6‐APA) (2) was used as starting material. Protection of the functional groups and activation of the C‐6 position were effected by converting 6‐APA successively into the Schiff base 13, the methyl ester 14 and the copper complex 15. The latter gave with benzaldehyde the C‐6 monosubstituted complex 17, and with formaldehyde the disubstituted complex 18. The direct α‐hydroxybenzylation of 6‐APA at C‐6 was also carried out with an excess of benzaldehyde at pH 7,5 leading to the SCHIFF base 19. Mild hydrolysis of 19 gave 6‐amino‐6‐(α‐hydroxybenzyl)‐penicillanic acid (21). Phenylacetylation of the latter yielded the penicillin G analogue 22. Direct reaction of 6‐APA with formaldehyde took place only in the presence of salicylaldehyde, giving the oxazolidine 24, from which the amino acid 25 could not be obtained. The new compounds showed only weak antibacterial activity as compared with penicillin G.
• Synthesis of 6-methylthiopenicillins and 7-heteroatom-substituted cephalosporins
  作者：William A. Slusarchyk、Harold E. Applegate、Phillip Funke、William Koster、Mohinder S. Paur、Marian Young、Joseph E. Dolfini

  DOI：10.1021/jo00945a023

  日期：1973.3
• 6-Arylthio penicillanic acid and derivatives thereof
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03965093A1

  公开（公告）日：1976-06-22

  Disclosed herein are penicillanic acids and derivatives thereof which are substituted in the 6-position, processes for preparing such compounds and the utility thereof. The compounds of the invention have been found to be useful as antibacterial agents.

  本文披露了在6位取代的青霉酸及其衍生物，以及制备这些化合物的过程和其用途。本发明的化合物被发现可用作抗菌剂。