6-aminopenicillanic acid methyl ester | 13789-47-4

• 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-aminopenicillanic acid methyl ester
• 英文别名: methyl 6(R)-aminopenicillanate；methyl 6-aminopenicillanate；6-APA methyl ester；6β-amino-penicillanic acid methyl ester；6β-Amino-penicillansaeure-methylester；6-Amino-penicillansaeuremethylester；Methyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 13789-47-4
• 化学式: C₉H₁₄N₂O₃S
• 分子量: 230.288
• InChiKey: ISECBIUYXKIUIS-JCGDXUMPSA-N

物化性质

• 熔点：
  47-49 °C
• 沸点：
  376.5±42.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-aminopenicillanic acid methyl ester 在 potassium permanganate 、 硫酸 作用下， 以 乙腈 为溶剂， 以75%的产率得到methyl 6β-aminopenicillanate 1,1-dioxide
  参考文献：
  名称：

  Domino functionalizations of the amino terminus of 6-aminopenicillanates with Ph3PCCO

  摘要：

  6-Aminopenicillanates, or the sulfoxides or the sulfones thereof, were N-acylated in a three-component reaction with an aldehyde and Ph3PCCO to give the corresponding 6-(E-2'-alkenoyl)amides. This domino addition-Wittig alkenation sequence was extended by an additional Claisen rearrangement step in the side-chain in the case of 5g. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.083
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 生成 6-aminopenicillanic acid methyl ester
  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

• The reactions of N-trimethylsilyl substituted ethers of α- and β-amino acids with sulfur tetrafluoride and morpholinosulfur trifluoride
  作者：Sergiy Zasukha、Andrii Khairulin、Yuriy Shermolovich

  DOI：10.1080/17415993.2021.1912045

  日期：2021.9.3

  The reactions of N-trimethylsilyl derivatives of α- and β-amino acid esters with sulfur tetrafluoride lead to the formation of the corresponding difluorides of imidosulfurous acids F2S=N-X (X = α or β-amino acid residue). The reaction products of difluorides with N-trimethylsilylmorpholine are ketimines or aldimines of new types, containing an imine fragment =N-S-NR2 at the α- or β-carbon atom of the

  摘要 α-和β-氨基酸酯的N-三甲基甲硅烷基衍生物与四氟化硫的反应导致形成相应的亚氨基亚硫酸F 2 S=NX（X=  α或β-氨基酸残基）的二氟化物。二氟化物与N-三甲基甲硅烷基吗啉的反应产物是新型酮亚胺或醛亚胺，在氨基酸的α-或β-碳原子上含有一个亚胺片段=NS-NR 2。二氟化物F 2 S=NX与α-和β的N-三甲基甲硅烷基酯的反应-氨基酸导致形成以前未知的硫二亚胺衍生物，其中氨基酸残基位于-N=S=N-组的氮原子上。
• Plant coumarins: VII. Amination of oreoselone trifluoromethanesulfonate
  作者：A. V. Lipeeva、E. E. Shul’ts、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428011090235

  日期：2011.9

  Amination of oreoselone trifluoromethanesulfonate with N-substituted piperazines, anabasine, aniline derivatives, quinolin- and isoquinolinamines, and amino acids of the penicillin and cephalosporin series in the presence of palladium complexes gave the corresponding N-substituted 3-aminofurocoumarins. The yield of the amination products depended on the catalytic system and base used.

  在钯配合物的存在下，用N-取代的哌嗪，鸟嘌呤，苯胺衍生物，喹啉和异喹啉胺以及青霉素和头孢菌素系列的氨基酸胺化三氟甲磺酸甲醚，得到相应的N-取代的3-氨基呋喃香豆素。胺化产物的产率取决于所使用的催化体系和碱。
• Silicon in synthesis: stabase adducts - a new primary amine protecting group: alkylation of ethyl glycinate
  作者：Stevan Djuric、John Venit、Philip Magnus

  DOI：10.1016/s0040-4039(01)90439-3

  日期：1981.1

  A new silicon-based protecting group for primary amines has been developed. Its usefulness is illustrated in a simple synthesis of an alkylated amino acid derivative.

  已经开发出一种新的基于伯胺的硅基保护基。在烷基化氨基酸衍生物的简单合成中说明了其有用性。
• A synthesis of cephamycins from cephalosporins and related reactions.
  作者：TAKEO KOBAYASHI、KIMIO IINO、TETSUO HIRAOKA

  DOI：10.1248/cpb.27.2727

  日期：——

  The sulfinamides 3 were transformed to sulfenimines 4 by treatment with thionyl chloride and a weak base such as quinoline (or triethylamine). The sulfenimines 4 were methoxylated with lithium methoxide to give 7α-methoxysulfenamides 5, which were directly acylated with an acyl chloride to furnish cephamycin derivatives 6. There was a major difference between the acylation of 7α-methoxysulfenamides 5 and that of the 7α-H derivatives 7. Reduction of the imines 4a with metal hydrides gave 7β-sulfenaminocephalosporins 12 together with a small amount of the 7α-isomers 13. The synthetic sequence 4a→12→14 provides a useful method for the isomerization of 7α-aminocephalosporins 17 to the corresponding 7β-isomers 18.

  用亚硫酰氯和弱碱（如喹啉或三乙胺）将亚磺酰胺 3 转化为亚磺酰亚胺 4。亚磺酰亚胺 4 与甲醇锂发生甲氧基化反应，生成 7α-甲氧基亚磺酰胺 5，然后直接与酰基氯发生酰基化反应，生成头霉素衍生物 6。7α-Methoxysulfenamides 5 的酰化过程与 7α-H 衍生物 7 的酰化过程有很大不同。用金属氢化物还原亚胺 4a，可得到 7β-亚磺酰胺头孢菌素 12 以及少量 7α 异构体 13。合成序列 4a→12→14 为 7α 氨基头孢菌素 17 异构化为相应的 7β 异构体 18 提供了有用的方法。
• N-Alkylderivate der 6-Amino-penicillansäure
  作者：Walter Dückheimer、Manfred Schorr

  DOI：10.1002/jlac.19677020120

  日期：1967.3.21

  Die Umsetzung von 6-Amino-penicillansäure (1) mit Diazomethan und Diazoäthan führt zu einem Gemisch verschieden weit alkylierter Ester 2–4 und 5–7, die durch Säulenchromatographie an Kieselgel voneinander getrennt werden. Durch Acylierung der Ester 3 und 6 mit Phenyl- und Phenoxy-acetylchlorid erhält man die 6-N-monoalkylierten Penicillinester 10, 11 und 13, die zu den 6-N-Alkyl-penicillinen 16–18

  的6-氨基青霉烷酸（反应1）与重氮甲烷和重氮乙烷导致的不同远烷基化酯的混合物2 - 4和5 - 7，其通过柱色谱法在硅胶上分离。通过酯的酰化3，和6与苯基和苯氧基乙酰氯的6-得到Ñ -monoalkylierten Penicillinester 10，11和13属于6- Ñ青霉素烷基- 16 - 18被皂化。新的青霉素衍生物具有弱的抗菌性能。