3-甲基-7-氧代-3-头孢烯-4-羧酸叔丁酯 | 57792-75-3

• 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
• 中文名称: 3-甲基-7-氧代-3-头孢烯-4-羧酸叔丁酯
• 英文名称: 3-methyl-7-oxo-3-cepheme-4-carboxylic acid tert-butyl ester
• 英文别名: 7-oxo-3-methylceph-3-em-4-carboxylic acid tert-butyl ester；7-oxodeacetoxycephalosporanic acid tert-butyl ester；tert-butyl 3-methyl-7-oxoceph-3-em-4-carboxylate；t-Butyl 3-methyl-7-oxoceph-3-em-4-carboxylate；tert-butyl (6R)-3-methyl-7,8-dioxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 57792-75-3
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: PQOJYCPTDDMWFE-SNVBAGLBSA-N

物化性质

• 沸点：
  388.7±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-甲基-7-氧代-3-头孢烯-4-羧酸叔丁酯 在 N-溴代丁二酰亚胺(NBS) 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 Z-3-bromomethyl-7-(4-nitrobenzylidene)deacetoxycephalosporanic acid sulfone tert-butyl ester
  参考文献：
  名称：

  Bromination of tert-Butyl Esters of 7α-Chloro and 7-Alkylidenedeacetoxycephalosporanic Acid Sulfones

  摘要：

  DOI：

  10.1007/s10593-005-0199-z
• 作为产物：
  描述：

  tert-butyl 7-aminodeacetoxycephalosporanate 在 草酸 、 N-甲基吡啶-4-羰甲醛苯磺酸盐 、 三乙胺 作用下， 生成 3-甲基-7-氧代-3-头孢烯-4-羧酸叔丁酯
  参考文献：
  名称：

  Mild and simple biomimetic conversion of amines to carbonyl compounds

  摘要：

  DOI：

  10.1021/ja00380a019

文献信息

• Synthesis and biological activity of alkylidene-substituted cephems and penams
  作者：I. Potorocina、M. Vorona、I. Shestakova、I. Domracheva、E. Liepinsh、G. Veinberg

  DOI：10.1007/s10593-011-0832-y

  日期：2011.9

  tert-butyl esters of new cephalosporin and penicillin analogs with an alkylidene substituent in the β-lactam ring. Most of these products were oxidized by meta-chloroperbenzoic acid to the corresponding sulfones. The cephemes and penams synthesized including the oxidized products displayed high cytotoxicity relative to cancer cells in vitro. Some of the alkylidene-substituted cephems as the free acids

  3-甲基-7-氧代辛酸-3-em-4-羧酸的叔丁基酯和6-氧代西杨酸与一系列的2-氧代亚烷基（三苯基）正膦酸酯的缩合反应得到了新的头孢菌素和青霉素类似物的叔丁基酯在β-内酰胺环上带有亚烷基取代基。这些产物大多数被间氯过苯甲酸氧化为相应的砜。头孢和戊烯合成包括氧化产物表现出较高的细胞毒性相对于癌细胞在体外。一些亚烷基取代的头孢烯作为游离酸，类似于他唑巴坦，抑制阴沟肠杆菌青霉素酶的催化活性。
• Synthesis and cytotoxic properties of derivatives of the tert-butyl ester of 7-alkylidene-3-methyl-3-cepheme-4-carboxylic acid
  作者：M. Vorona、I. Potorocina、G. Veinberg、I. Shestakova、I. Kanepe、E. Lukevics

  DOI：10.1007/s10593-008-0099-0

  日期：2008.6

  Sulfones of the tert-butyl esters of 7-arylmethylene-and 7-(2-furyl)methylene-3-methyl-3-cepheme-4-carboxylic acid were obtained by the condensation of the tert-butyl ester of 3-methyl-7-oxo-3-cepheme-4-carboxylic acid with arylmethylene-and 2-furylidenetriphenylphosphoranes and subsequent oxidation of the intermediate products by meta-chloroperbenzoic acid. The combination of the tert-butyl esters of 7E-bromomethylene-and 7,7-dibromomethylene-3-methyl-1,1-dioxo-3-cepheme-4-carboxylic acids with trimethylsilylacetylene under conditions of the Sonogashira reaction gave the tert-butyl esters of 3-methyl-1,1-dioxo-7E-(3-trimethylsilyl-2-propynylidene)-3-cepheme-4-carboxylic acid and 3-methyl-1,1-dioxo-7-[1,5-bis(trimethylsilyl)-1,4-pentadiyn-3-ylidene]-3-cepheme-4-carboxylic acid. The Vilsmeier reagent was used to incorporate the dimethylaminomethylene group at C-2 of the 7Z-and 7E-isomers of the tert-butyl ester of 7-(4-chlorophenyl)methylene-3-methyl-1,1-dioxo-3-cepheme-4-carboxylic acid. The cytotoxic properties of the derivatives of the tert-butyl ester of 7-alkylidene-3-methyl-3-cepheme-4-carboxylic acid in regard to cancer and normal cells in vitro depends on the structure and 7Z-or 7E-isomerism of the substituent in the 7-alkylidene group as well as the presence of a dimethylaminomethylene group at C-2 of the 3-cepheme system.
• Synthesis and stereoisomerism of derivatives of tert-butyl 7-alkylideneceph-3-em-4-carboxylate
  作者：M. Vorona、G. Veinberg、S. Belyakov、M. Petrova、E. Liepinsh、E. Lukevics

  DOI：10.1007/s10593-008-0067-8

  日期：2008.4

  By condensation of tert-butyl 3-methyl-7-oxoceph-3-em-4-carboxylate and its 3-acetoxymethyl analog with acetylmethylenetriphenylphosphorane and 3-trimethylsilylpropyn-2-ylindenetriphenylphosphorane tert-butyl 7Z-acetylmethylene-3-methylceph-3-em-4-carboxylate and also 7Z-and 7E-isomers of tert-butyl 3-acetoxymethyl-7-(3-trimethylsilylpropyn-2-ylidene)ceph-3-em-4-carboxylates were synthesized. Oxidation of these compounds with 1 equivalent of meta-chloroperbenzoic acid gave their 1R-and 1S-sulfoxides, and oxidation with 2 equivalents gave the corresponding sulfones. According to data from H-1 NMR spectroscopy, the carbonyl of the beta-lactam descreens proton H-9 of the alkylidene group in the 7Z-isomers more strongly than in the 7E-isomers, shifting their signals to weaker field. Analogous shifts of the H-6 signal to weaker field was observed in the 1R-sulfoxides in comparison with that for the 1S-sulfoxide. These results were confirmed by X-ray crystallography of tert-butyl 7Z-acetylmethylene-3-methyl-1S-oxoceph-3-em-4-carboxylate and tert-butyl 7Z-acetylmethylene-3-methyl-1,1-dioxoceph-3-em-4-carboxy-late.
• FERRI, V.;PALLAVACINI, M.;VALOTI, E.;VILLA, L.;DALLASTA, L.;PESSA, A., FRAMACO, 46,(1991) N, C. 191-207
  作者：FERRI, V.、PALLAVACINI, M.、VALOTI, E.、VILLA, L.、DALLASTA, L.、PESSA, A.

  DOI：——

  日期：——