methyl 6β-(triphenylmethylamino)penicillinate | 21027-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 6β-(triphenylmethylamino)penicillinate
• 英文别名: 6β-tritylamino-penicillanic acid methyl ester；6β-Tritylamino-penicillansaeure-methylester；D-α-6-Triphenylmethylamino-penicillansaeure-methylester；Methyl 6β-(triphenylmethylamino)-penicillanat；methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(tritylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 21027-18-9
• 化学式: C₂₈H₂₈N₂O₃S
• 分子量: 472.608
• InChiKey: NVBHPHXBDXSWJB-GIFXNVAJSA-N

物化性质

• 沸点：
  616.2±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6β-(triphenylmethylamino)penicillinate 在 吡啶 、 盐酸 、 sodium hydroxide 、 异丙醇 作用下， 生成 6-氨基青霉烷酸
  参考文献：
  名称：

  A GENERAL SYNTHESIS OF THE PENICILLINS

  摘要：

  DOI：

  10.1021/ja01530a079
• 作为产物：
  描述：

  6-氨基青霉烷酸 以 乙醚 、 二氯甲烷 为溶剂， 生成 methyl 6β-(triphenylmethylamino)penicillinate
  参考文献：
  名称：

  Substitution der 6-Aminopenicillansäure am Kohlenstoffatom 6

  摘要：

  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.

  DOI：

  10.1002/hlca.19680510812

文献信息

• Chemistry of secopenicillins. Part I: The nayler reaction revisited
  作者：Ching-Pong Mak、Hans Fliri

  DOI：10.1016/s0040-4039(00)99064-6

  日期：1985.1

  Reaction of several penicillin derivatives 1a- 1g with sodium hydride/methyl iodide gave secopenicillins 2a-2g. A mechanism for this reaction proposed.

  几种青霉素衍生物1a-1g与氢化钠/甲基碘的反应产生了secopenicillins 2a-2g。提出了该反应的机制。
• <b>The Total and Partial General Syntheses of the Penicillins</b>
  作者：John C. Sheehan、Kenneth R. Henery-Logan

  DOI：10.1021/ja00874a029

  日期：1962.8
• 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.
• A GENERAL SYNTHESIS OF THE PENICILLINS
  作者：John C. Sheehan、Kenneth R. Henery Logan

  DOI：10.1021/ja01530a079

  日期：1959.11