3-(S)-phenoxyacetamido-4-(S)-acetoxyazetidinone | 82863-24-9

• 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: 3-(S)-phenoxyacetamido-4-(S)-acetoxyazetidinone
• 英文别名: 4-(R,S)-acetoxy-3-(S)-(phenoxyacetamido)azetidinone；4-acetoxy-3-phenoxyacetamido-azetidin-2-one；[4-Oxo-3-[(2-phenoxyacetyl)amino]azetidin-2-yl] acetate
• CAS: 82863-24-9
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: JOSXTSZPEJSZFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (三甲基硅基)甲基氯化镁 、 3-(S)-phenoxyacetamido-4-(S)-acetoxyazetidinone 以 四氢呋喃 为溶剂， 以42%的产率得到N-((3S,4R)-2-Oxo-4-trimethylsilanylmethyl-azetidin-3-yl)-2-phenoxy-acetamide
  参考文献：
  名称：

  Synthetic approaches towards 4-(silylmethyl)-2-azetidinones

  摘要：

  Differently substituted 4-(silylmethyl)-2-azetidinones were prepared starting form the corresponding 4-acetoxy-2-azetidinones with silylmethylmagnesium chlorides. The same kind of beta-lactams were synthesized ''via'' cycloaddition of allylsilanes and chlorosulfonyl isocyanate (CSI).

  DOI：

  10.1016/s0040-4039(00)79698-5

文献信息

• Clavulanic acid derivatives, their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0001333A1

  公开（公告）日：1979-04-04

  This invention provides the compounds of the formula (I): and salts and esters thereof, wherein R1 is a hydrogen atom or a lower alkyl, aryl or aralkyl group, R2 and R3 are independently hydrogen, aryl, aralkyl, lower alkyl or substituted lower alkyl, or R3 is joined to R1 to form a 4-, 5-, or6- membered ring or is joined to R2 to form a 5- or 6- membered ring. The compounds have β-lactamase inhibitory and anti- bacterial properties. The invention also provides a process for their preparation, and pharmaceutical compositions containing them.

  本发明提供了式(I)化合物： 及其盐和酯，其中 R1 是氢原子或低级烷基、芳基或芳烷基，R2 和 R3 独立地是氢、芳基、芳烷基、低级烷基或取代的低级烷基，或 R3 与 R1 连接形成 4、5 或 6 分子环，或与 R2 连接形成 5 或 6 分子环。 这些化合物具有β-内酰胺酶抑制和抗菌特性。 本发明还提供了制备它们的工艺和含有它们的药物组合物。
• A novel process for carbon-carbon bond formation at the C-4 position of 3-acylaminoazetidinones
  申请人：ELI LILLY AND COMPANY

  公开号：EP0163452A1

  公开（公告）日：1985-12-04

  The invention emcompasses a process for stereoselective carbon-carbon bond formation at the C-4 position of a 3 -(acylamino) azetidinone. The process is carried out under free radical conditions using a (2-substituted or unsubstituted allyl) tin reagent.

  本发明包括一种在 3-(酰氨基)氮杂环丁酮的 C-4 位立体选择性碳-碳键形成的工艺。 该工艺在自由基条件下使用（2-取代或未取代的烯丙基）锡试剂进行。
• Novel antimicrobial lactam-quinolones
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0366189A2

  公开（公告）日：1990-05-02

  Antimicrobial lactam-quinolone compounds comprising a lactam-containing moiety linked to a quinolone moiety, of the formula: wherein (1) A', A2, A3, R1, R4 and R6 generally form any of a variety of quinolone, naphthyridine or related cyclic moieties known in the art to have animicrobial activity; and (2) R' or R3 contain a linking moiety, linking the quinolone moiety to a lactam-containing moiety having the formula: wherein (3) R10, R11, R12, R13, and R14, together with bonds "a" and "b", form any of a variety of lactam-containing moieties known in the art to have antimicrobial activity; and (4) the linking moiety includes (for example) carbamate, dithiocarbamate, urea, thiourea, isouronium, isothiouronium, guanidine, carbonate, trithiocarbonate, reversed carbamate, xanthate, reversed isouronium, reversed dithiocarbamate, reversed isothiouronium, amine, imine, ammonium, heteroarylium, ether, thioether, phosphone, phosphoramide, phosphate, sulfonamide, ester, thioester, amide, and hydrazide groups.

  抗菌内酰胺-喹诺酮化合物，包括与喹诺酮分子相连的含内酰胺分子，其分子式为 其中 (1) A'、A2、A3、R1、R4 和 R6 通常构成本领域已知的具有抗菌活性的各种喹诺酮、萘啶或相关环状分子中的任一种；以及 (2) R' 或 R3 含有连接基团，将喹诺酮基团与具有以下式子的含内酰胺基团连接起来： 其中 (3) R10、R11、R12、R13 和 R14 与键 "a "和 "b "一起构成本领域已知的具有抗菌活性的各种含内酰胺分子中的任一种；以及 (4) 连接分子包括（例如）氨基甲酸酯、二硫代氨基甲酸酯、脲、硫脲、异乌拉 铵、异硫乌拉铵、胍、碳酸盐、三硫代碳酸盐、反向氨基甲酸酯、黄原酸盐、反向异乌拉 铵、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反向二硫代氨基甲酸酯、反转二硫代氨基甲酸酯、反转异硫脲、胺、亚胺、铵、杂芳脲、醚、硫醚、膦、磷酰胺、磷酸盐、磺酰胺、酯、硫酯、酰胺和酰肼基团。
• Novel antimicrobial quinolonyl lactams
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0366193A2

  公开（公告）日：1990-05-02

  Antimicrobial quinolonyl lactam compounds comprising a lactam-containing moiety linked, by a non-ester linking moiety, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: wherein (1) R3, R4, and R5, together with bonds "a" and "b", form any of a variety of lactam-containing moieties similar to those known in the art to have antimicrobial activity; (2) A, R6, R7, and R8 form any of a variety of quinolone or naphthyridine structures similar to those known in the art to have antimicrobial activity; and (3) Y, together with R5, form a variety of non-ester linking moieties between the lactam-containing moiety and the quinolone moiety.

  抗菌喹烯酮内酰胺化合物，其包含的内酰胺分子通过非酯连接分子与喹烯酮分子的 3-羧基相连。这些化合物的结构式如下 其中 (1) R3、R4 和 R5，与键 "a "和 "b "一起，构成与本领域已知的具有抗菌活性的含内酰胺分子类似的各种含内酰胺分子中的任何一种； (2) A、R6、R7 和 R8 形成各种喹诺酮或萘啶结构中的任何一种，类似于本领域已知的具有抗菌活性的结构；以及 (3) Y 与 R5 一起在含内酰胺的分子和喹诺酮分子之间形成各种非酯连接分子。
• US4215128A
  申请人：——

  公开号：US4215128A

  公开（公告）日：1980-07-29