3-methyl-2-(7-oxo-3-phenoxymethyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid methyl ester | 52512-73-9

• 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: 3-methyl-2-(7-oxo-3-phenoxymethyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid methyl ester
• 英文别名: 3-methyl-2-((1S)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid methyl ester；(1S, 5R)-6-(1-methoxycarbonyl-2-methyl-1-propenyl)-3-phenoxymethyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one；methyl 3-methyl-2-[(1S,5R)-7-oxo-3-(phenoxymethyl)-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]but-2-enoate
• CAS: 52512-73-9
• 化学式: C₁₇H₁₈N₂O₅
• 分子量: 330.34
• InChiKey: FGFDRDXMVFCQDC-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 在 magnesium chloride 作用下， 以 甲醇 、 叔丁醇 为溶剂， 以74%的产率得到3-methyl-2-(7-oxo-3-phenoxymethyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid methyl ester
  参考文献：
  名称：

  Prominent Aspects of Electroorganic Synthesis in β-Lactam Chemistry

  摘要：

  AbstractThe potentiality of electrolysis procedures in the penicillin‐cephalosporin conversion as well as in the direct transform of penicillins into oxazolineazetidinones as an intermediate for the preparation of the sulfur‐free analogues of cephalosporins are discussed. Especially, a chemoselective electrolytic chlorination of methyl group of 3‐methyl‐3‐butenoate moiety of thiazolineazetidinone derived from penicillins, a direct synthesis of 3′‐thiosubstituted cephalosporins from the thiazoline‐azetidinones, an improved synthesis of exomethylenecephams, an efficient route to 3‐chloromethyl‐Δ3‐cephems, electrochemical S‐S bond fission of 4‐(2‐benzothiazolyldithio) azetidinones, a direct transformation of penicillins into oxazoline‐azetidinones by chloride salt‐promoted electrolysis, and a versatile intermediate for new β‐lactam antibiotics are presented.

  DOI：

  10.1002/bscb.19820911202

文献信息

• Studies related to penicillins. Part XI. Mechanism of degradation of benzylpenicillinic and phenoxymethylpenicillinic acid by mercury(II) acetate
  作者：Richard J. Stoodley、Nigel R. Whitehouse

  DOI：10.1039/p19740000181

  日期：——

  Acetoxymercury(II)(2S)-3-acetoxymercurio(II)thio-2-(1R,5S)-3-benzyl-6-oxo-2-oxa-4,7-diazabicyclo[3.2.0]-hept-3-en-7-yl}-3-methylbutanoate (16) is formed when potassium benzylpenicillinate (1) is added to mercury(II) acetate in acetic acid. The salt (16) is converted into (3S, 4S)-4-acetoxy-1-(2-methylprop-1-enyl)-3-phenylacetamidoazetidin-2-one (6) by hot acetic acid, into (1R,5S)-3-benzyl-7-(2-m

  乙酰氧基汞（II）（2 S）-3-乙酰氧基汞（II）thio-2-（1 R，5 S）-3-苄基-6-氧代-2-氧杂-4,7-二氮杂双环[3.2.0]当将苄基青霉酸钾（1）加到乙酸的乙酸汞（II）中时，形成-庚-3-en-7-基} -3-甲基丁酸（16）。盐（16）通过热乙酸转化为（3 S，4 S）-4-乙酰氧基-1-（2-甲基丙-1-烯基）-3-苯基乙酰氨基氮杂环丁烷-2-酮（6），转化为（1 R，5 S）-3-苄基-7-（2-甲基丙-1-烯基）-2-氧杂-4,7-二氮杂双环[3.2.0]庚-3-en-6-二甲基（10）亚砜，并转化为甲基（2 S）-2-（1 R，5 S）-3-重氮甲烷制得）-3-苄基-6-氧代-2-氧杂-4,7-二氮杂双环[3.2.0]庚-3-烯-7-基} -3-巯基-3-甲基丁酸酯（15）。吡啶从盐（16）中除去乙酸汞（II）的元素，得到衍生物（21）。
• Process for preparing oxazolineazetidinone derivatives
  申请人：Otsuka Kagaku Yakuhin Kabushiki Kaisha

  公开号：US04379032A1

  公开（公告）日：1983-04-05

  This invention provides a process for preparing an oxazolineazetidinone derivative represented by the formula ##STR1## (wherein R.sup.1 represents hydrogen atom, alkyl group, alkenyl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted aryloxymethyl group, R.sup.2 represents free or protected carboxyl group and R.sup.3 represents hydrogen atom or methoxy group) from a penicillin derivative represented by the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sub.3 are as defined above.

  本发明提供了一种制备由以下式子表示的氧唑啉-氮杂环己酮衍生物的方法：##STR1## （其中 R1代表氢原子、烷基、烯基、取代或未取代的芳基甲基、取代或未取代的芳基、或取代或未取代的芳基氧甲基，R2代表自由或保护的羧基，R3代表氢原子或甲氧基），该方法从以下式子表示的青霉素衍生物中制备：##STR2## 其中R1、R2和R3如上所定义。
• Prominent Aspects of Electroorganic Synthesis in β-Lactam Chemistry
  作者：Sigeru Torii、Hideo Tanaka、Michio Sasaoka、Norio Saitoh、Takashi Siroi、Junzo Nokami

  DOI：10.1002/bscb.19820911202

  日期：——

  AbstractThe potentiality of electrolysis procedures in the penicillin‐cephalosporin conversion as well as in the direct transform of penicillins into oxazolineazetidinones as an intermediate for the preparation of the sulfur‐free analogues of cephalosporins are discussed. Especially, a chemoselective electrolytic chlorination of methyl group of 3‐methyl‐3‐butenoate moiety of thiazolineazetidinone derived from penicillins, a direct synthesis of 3′‐thiosubstituted cephalosporins from the thiazoline‐azetidinones, an improved synthesis of exomethylenecephams, an efficient route to 3‐chloromethyl‐Δ3‐cephems, electrochemical S‐S bond fission of 4‐(2‐benzothiazolyldithio) azetidinones, a direct transformation of penicillins into oxazoline‐azetidinones by chloride salt‐promoted electrolysis, and a versatile intermediate for new β‐lactam antibiotics are presented.