(6R-反式)-3-甲基-8-氧代-7-(苯基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸二苯基甲基酯 | 29126-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: (6R-反式)-3-甲基-8-氧代-7-(苯基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸二苯基甲基酯
• 英文名称: diphenylmethyl (6R-trans)-3-methyl-8-oxo-7-(phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 英文别名: diphenylmethyl 7α-phenylacetamido-3-methyl-3-cephem-4-carboxylate；Diphenylmethyl(6r,7r)-3-methyl-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；benzhydryl (6R,7R)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 29126-12-3
• 化学式: C₂₉H₂₆N₂O₄S
• 分子量: 498.602
• InChiKey: KRSQRWDTNJRUNK-UFHPHHKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6R-反式)-3-甲基-8-氧代-7-(苯基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸二苯基甲基酯 在 N-氯代丁二酰亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 生成 diphenylmethyl 7α-phenylacetamido-2α-methoxy-3-methyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  Symmetrical azetidinone aldehyde disulfides and process

  摘要：

  通过将相应的7α-酰基氨基-2α-烷氧基-3-甲基-3-头孢烯-4-羧酸酯首先与N-氯卤代试剂（例如N-氯丁二酰亚胺）反应，然后与汞二氯化物和碳酸镉的水悬浮液反应，制备4R，4'R双[1-（2-N-3-甲基-4-丙烯酸-Z-丁-2-烯酯）-2-氧代-3S-酰胺基氮杂环丙烷]二硫化物化合物。本发明制备的二硫化物化合物是生物活性的7β-酰基氨基-7α-烷氧基-3-甲基-1-氧代-β-内酰胺抗生素化合物的合成中间体。

  公开号：

  US04293495A1
• 作为产物：
  描述：

  diphenylmethyl 7β-phenylacetamido-3-acetoxymethyl-3-cephem-4-carboxylate 在 吡啶 、 indium 、 三甲基氯硅烷 、 potassium iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 27.0h， 生成 (6R-反式)-3-甲基-8-氧代-7-(苯基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸二苯基甲基酯
  参考文献：
  名称：

  A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media

  摘要：

  An efficient reductive conversion of 3-iodomethylcephalosporin and 3-acetoxymethylcephalosporin derivatives mediated by indium into the corresponding 3-methylcephems and 3-methylenecephams in moderate to good yields has been developed in an aqueous system. 3-Methylenecephams are converted into the corresponding 3-methylcephems under previously reported basic conditions quantitatively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00512-8

文献信息

• Azetidinone alcohol disulfides and process for cyclization
  申请人：Eli Lilly and Company

  公开号：US04293493A1

  公开（公告）日：1981-10-06

  Azetidinone alcohol disulfides are synthesized by reduction of the corresponding aldehydes. The azetidinone alcohol disulfides are the substrates for a process which cyclizes these compounds to 1-oxa .beta.-lactam compounds, employing a cyclizing reagent chosen from the class consisting of divalent mercury salts or trivalent phosphine compounds. The 1-oxa .beta.-lactam compounds produced by this process are intermediates in the synthesis of 1-oxa .beta.-lactam antibiotics.

  Azetidinone醇二硫醚通过还原相应的醛合成。Azetidinone醇二硫醚是一个过程的底物，该过程将这些化合物环化为1-氧代β-内酰胺化合物，使用的环化试剂来自于二价汞盐或三价膦化合物类。通过这一过程产生的1-氧代β-内酰胺化合物是1-氧代β-内酰胺类抗生素合成中的中间体。
• Unsymmetrical azetidinone aldehyde disulfides and process
  申请人：Eli Lilly and Company

  公开号：US04302391A1

  公开（公告）日：1981-11-24

  Aryl 4R[1-(2-N-3-methyl-4-al-Z-but-2-ene-oate)-2-oxo-3S-acylamino azetidinone]disulfides are prepared by reacting the corresponding 7.alpha.-acylamino-2.alpha.-alkoxy-3-methyl-3-cephem-4-carboxylates first with either phenylsulfenyl chloride or a monosubstituted-phenylsulfenyl chloride where the substituent is either chloro, methoxy, methyl or acetoxy. The disulfide compounds produced in this invention are intermediates in the synthesis of the 7.beta.-acylamino-7.alpha.-alkoxy-3-methyl 1-oxa .beta.-lactam acids, a class of antibiotic compounds.

  Aryl 4R [1-（2-N-3-甲基-4-烯基-2-烯氧基）-2-氧代-3S-酰胺基氮杂环己烷] 二硫化物是通过首先将相应的7.alpha.-酰胺基-2.alpha.-烷氧基-3-甲基-3-头孢烯-4-羧酸酯与苯基硫酰氯或单取代苯基硫酰氯反应制备而成，其中取代基为氯，甲氧基，甲基或乙酰氧基。本发明中产生的二硫化合物是7β-酰胺基-7α-烷氧基-3-甲基-1-氧代-β-内酰胺酸的合成中间体，这是一类抗生素化合物。
• A facile synthesis of cephem side chains by palladium catalyzed cross-coupling of 3-substituted-Δ3-cephems with dialkylzinc or vinyltributyltin
  作者：Michele Contento、Marco Da Col、Paola Galletti、Sergio Sandri、Achille Umani-Ronchi

  DOI：10.1016/s0040-4039(98)01940-6

  日期：1998.11

  Synthesis of 3-vinyl- and 3-alkyl-Delta(3)-cephems was performed in a regioselective manner by palladium acetate catalyzed reaction of 3-sulfonato- or 3-bromo-Delta(3)-cephems with dialkylzinc or vinyltributyltin. A new access to 3-alkyl-Delta(3)-cephems is opened, starting from the allenyl compound 10. (C) 1998 Elsevier Science Ltd. All rights reserved.
• MICETICH, R. G.;SHAW, CHIA-CHENG
  作者：MICETICH, R. G.、SHAW, CHIA-CHENG

  DOI：——

  日期：——