(3R,4RS)-4-acetoxy-3-bromoazetidin-2-one | 103022-12-4

• 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: (3R,4RS)-4-acetoxy-3-bromoazetidin-2-one
• 英文别名: 3(R)-bromo-4(R,S)-acetoxyazetidin-2-one；(3R)-4-Acetoxy-3-bromoazetidinone；[(3R)-3-bromo-4-oxoazetidin-2-yl] acetate
• CAS: 103022-12-4；103067-72-7
• 化学式: C₅H₆BrNO₃
• 分子量: 208.012
• InChiKey: YHBHGWQTEGXDTR-WWLRPLJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三苯甲硫醇 、 (3R,4RS)-4-acetoxy-3-bromoazetidin-2-one 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 0.5h， 以60%的产率得到(3S,4R)-3-bromo-4-triphenylmethylthio-2-azetidinone
  参考文献：
  名称：

  Carbapenem and penem antibiotics. III. Synthesis and antibacterial activity of 2-functionalized-methyl penems related to asparenomycins.

  摘要：

  合成了具有C-6位1-(羟甲基)亚乙基或环状碳酸酯侧链的R构型和光学活性2-(杂芳基)硫代甲基青霉烯（24、51、63、65、37、40、69以及21b、61b、26b、30b、64b、35b、66b、39b、68b），并测定了它们的抗菌活性。

  DOI：

  10.1248/cpb.33.4371
• 作为产物：
  描述：

  (3R,4RS)-methyl 2-(4'-acetoxy-3'-bromo-2'-oxoazetidin-1'-yl)-3-methylbut-2-enoate 生成 (3R,4RS)-4-acetoxy-3-bromoazetidin-2-one
  参考文献：
  名称：

  （5 ）（）-6-[（1-甲基-1,2,3-三唑-4-基）亚甲基] -7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2的合成-羧酸，一种新型的碳青霉烯衍生物，来自6-氨基青霉烯酸

  摘要：

  标题化合物由6-氨基青霉烷酸制备的新的中间体，甲氧基苄基（5 ，6 ）的6-溴-7-氧代-1-氮杂双环〔3.2.0〕庚-2-烯-2-羧酸叔丁酯（10） 。

  DOI：

  10.1016/s0040-4039(00)99417-6

文献信息

• Carbapenem and penem antibiotics. IV. Carbapenem and penem antibiotics. V.Synthesis and antibacterial activity of 2-functionalized-methyl 1-methylcarbapenems related to asparenomycins.
  作者：Mitsuru IMUTA、Shoichiro UYEO、Tadashi YOSHIDA

  DOI：10.1248/cpb.39.658

  日期：——

  The synthesis of 1α- and/or 1β-methylcarbapenems, 2-unsubstituted and 2-(5-methyl-1, 3, 4-thiadiazol-2-yl)thiomethyl derivatives having a 1-(hydroxy)methylethylidene or cyclic carbonate side chain at the C-6 position, is described. The in vitro antibacterial activities of these compounds and their corresponding 1-unsubstituted carbapenems are compared.

  本文介绍了 1α- 和/或 1β- 甲基碳青霉烯类、2-未取代和 2-(5-甲基-1, 3, 4-噻二唑-2-基)硫代甲基衍生物的合成过程，这些衍生物在 C-6 位具有 1-(羟基)甲基亚乙基或环状碳酸酯侧链。比较了这些化合物和相应的 1-未取代碳青霉烯类化合物的体外抗菌活性。
• Synthesis of 6-(substituted methylene) carbapenem derivatives from 6-aminopenicillanic acid
  作者：Steven Coulton、Irene François

  DOI：10.1039/p19910002699

  日期：——

  The key intermediate in the preparation of novel 6-(substituted methylene) carbapenem derivatives is p-methoxybenzyl (5R,6R)-6-bromo-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 26, which was prepared in several steps from 6-aminopenicillanic acid 14 via (3R,4R)-4-allyl-3-bromoazetidin-2-one 21. Sequential treatment of the aforementioned ester 26 with either lithium diisopropylamide or lithium diphenylamide, 1-methyl-1H-1,2,3-triazole-4-carbaldehyde and acetic anhydride provided a diastereoisomeric mixture of acylated bromohydrins 28; reductive elimination then afforded the isomeric (E)- and (Z)-6-triazolylmethylene carbapenem esters 29 and 31, respectively. Lewis acid-mediated deprotection of the 6-bromo and 6-[(E)-triazolylmethylene] esters 26 and 29 gave the sodium salts of (5R,6R)-6-bromo-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 27 and (5R)-6-[(E)-(1-methyl-1H-1,2,3-triazol-4-yl)methylene]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 30, respectively.In addition, condensation of the anion, generated by deprotonation of the 6-bromo ester, with acetaldehyde, followed by acylation and reductive elimination furnished the isomeric (E)- and (Z)-ethylidene carbapenem esters.Whilst the (E)-6-triazolylmethylene carbapenem displayed low levels of antibacterial activity, it possessed no beta-lactamase-inhibitory activity whatsoever. The 6-bromocarbapenem was devoid of both antibacterial and beta-lactamase-inhibitory activity.
• COULTON, STEVEN;FRANCOIS, IRENE, TETRAHEDRON LETT., 30,(1989) N3, C. 3117-3120
  作者：COULTON, STEVEN、FRANCOIS, IRENE

  DOI：——

  日期：——