methyl 6-phenoxyacetamidopenicillanate-1β-oxide | 24652-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: methyl 6-phenoxyacetamidopenicillanate-1β-oxide
• 英文别名: methyl 6β-phenoxyacetamidopenicillanate；1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid methyl ester；Phenoxymethylpenicillin-(S)-sulfoxid-methylester；Penicillin-methylester-sulfoxid；methyl (2S,4S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4λ4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 24652-74-2
• 化学式: C₁₇H₂₀N₂O₆S
• 分子量: 380.422
• InChiKey: UDNQUKKUEOSXNO-YLYKPJARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 6-phenoxyacetamidopenicillanate-1β-oxide 以42%的产率得到
  参考文献：
  名称：

  BANVILLE, JACQUES;LAPOINTE, PHILIPPE;BELLEAU, BERNARD;MENARD, MARCEL, CAN. J. CHEM., 66,(1988) N 6, C. 1390-1399

  摘要：

  DOI：

文献信息

• Synthesis and reactivity of 6α-methoxy-2-methyl-6β-phenoxyacetamido-penem-3-carboxylates
  作者：Ettore Perrone、Richard J. Stoodley

  DOI：10.1039/c39820000933

  日期：——

  Representatives of the title compounds have been prepared from phenoxymethylpenicillinic acid; the β-lactam linkage of these compounds is exceptionally reactive.

  标题化合物的代表是从苯氧基甲基青霉烯酸制备的。这些化合物的β-内酰胺键具有极强的反应性。
• Nuclear analogs of β-lactam antibiotics. Synthesis of 6,6-disubstituted acylaminopenems
  作者：Jacques Banville、Philippe Lapointe、Bernard Belleau、Marcel Menard

  DOI：10.1139/v88-225

  日期：1988.6.1

  The preparation of 6α-methyl-2-methyl-6β-phenoxyacetamidopenem-3-carboxylate, 6α-methoxy-2-methyl-6β-phenoxyacetamidopenem-3-carboxylate, and 6α-methoxy-2-methyl-6β-phenylmalonylamidopenem-3-carboxylate from penicillin V and 6-aminopenicillanic acid is described. These penems have been isolated and characterized as their sodium or potassium salt. The chemical stability of the above compounds was determined as their half-life in aqueous buffer. In this way, it was found that the 6α-methyl analog was more stable than the parent 6-monosubstituted acylaminopenem while the remaining analogs were of comparable stability.

  描述了从青霉素V和6-氨基青霉烷酸制备6α-甲基-2-甲基-6β-苯氧乙酰胺基青霉烷-3-羧酸酯、6α-甲氧基-2-甲基-6β-苯氧乙酰胺基青霉烷-3-羧酸酯和6α-甲氧基-2-甲基-6β-苯基丙酰胺基青霉烷-3-羧酸酯的方法。这些青霉烷类化合物已被分离并表征为其钠盐或钾盐。通过在水溶液中测定它们的半衰期，确定了上述化合物的化学稳定性。通过这种方法，发现6α-甲基类似物比亲代6-单取代酰胺基青霉烷更稳定，而其余类似物的稳定性相当。
• Phosphorus in organic synthesis. XII. Amino acids and peptides. XXII. Reaction of penicillin sulfoxides with diethyl phosphorocyanidate (DEPC).
  作者：KUNIHIRO NINOMIYA、TAKAYUKI SHIOIRI、SHUNICHI YAMADA

  DOI：10.1248/cpb.24.2711

  日期：——

  Reaction of penicillin sulfoxides with diethyl phosphorocyanidate (DEPC) was investigated. Treatment of benzylpenicillin (S)-sulfoxide methyl ester (4a) with a slight excess of DEPC in N, N-dimethylacetamide gave the 3-cephem (5a), the 2-cephem (6a). and the 3-methylenecepham (7a) in 22, 4, and 4% yields, respectively. Increase of the quantity of DEPC to a three or five fold excess increased the yield of the 3-cephem (5a). Phenoxymethylpenicillin (S)-sulfoxide methyl ester (4b) also afforded the 3-cephem (5b) and the 3-methylenecepham (7b) under analogous reaction conditions as above, while phthalimidopenicillin (R)-sulfoxide methyl ester (8) furnished the 3-cephem (9) and the isothiazolones (10 and 11).

  研究了青霉素硫醚与膦氰酸二乙酯（DEPC）的反应。在 N，N-二甲基乙酰胺中用微量过量的 DEPC 处理苄青霉素 (S)-亚砜甲酯 (4a)，得到 3-头孢 (5a)、2-头孢 (6a) 和 3-亚甲基头孢 (7a)，产率分别为 22%、4% 和 4%。将 DEPC 的用量增加到过量的三倍或五倍，可提高 3-cephem（5a）的产率。在上述类似的反应条件下，吩氧甲青霉素（S）-亚砜甲酯（4b）也能生成 3-头孢菌素（5b）和 3-亚甲基头孢菌素（7b），而酞酰亚胺青霉素（R）-亚砜甲酯（8）能生成 3-头孢菌素（9）和异噻唑酮（10 和 11）。
• Transformations of penicillins: reactions of penam S-oxides with N-chloro-N-sodiocarbamates
  作者：David H. Bremner、Malcolm M. Campbell、Graham Johnson

  DOI：10.1039/p19770001943

  日期：——

  Penicillanate (S)-S-oxides reacted with ethyl N-chloro-N-sodiocarbamate to give 6α-ethoxyformamido-derivatives together with the corresponding 6-epi-penicillanate, an intermediate in the formation of the former product. The (R)-S-oxides reacted with N-chloro-N-sodiocarbamate to give 6α-alkoxyformamido-derivatives, together with 6,6-bis(alkoxyformamido)penam (R)-S-oxides, which were further transformed

  青霉酸酯（S）-S-氧化物与N-氯-N-磺基氨基甲酸酯乙酯反应，生成6α-乙氧基甲酰胺基衍生物以及相应的6-表-青霉酸酯，这是前一种产物形成过程中的中间体。的（[R ）-小号-oxides与反应Ñ氯代Ñ -sodiocarbamate得到6α-alkoxyformamido衍生物，连同6,6-双（alkoxyformamido）青霉烷（[R ）-小号-oxides，将其进一步转化成cephalosporanates 。讨论了这些取代反应的机理。
• Micetich, Ronald G.; Singh, Rajeshwar; Tetteh, Daniel M., Heterocycles, 1990, vol. 31, # 9, p. 1617 - 1628
  作者：Micetich, Ronald G.、Singh, Rajeshwar、Tetteh, Daniel M.、Morin, Robert B.

  DOI：——

  日期：——