benzhydryl 7-[(E)-prop-2'-enylidene]cephalosporanate 1,1-dioxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzhydryl 7-[(E)-prop-2'-enylidene]cephalosporanate 1,1-dioxide
• 英文别名: benzhydryl (6R,7E)-3-(acetyloxymethyl)-5,5,8-trioxo-7-prop-2-enylidene-5lambda6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；benzhydryl (6R,7E)-3-(acetyloxymethyl)-5,5,8-trioxo-7-prop-2-enylidene-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 化学式: C₂₆H₂₃NO₇S
• 分子量: 493.537
• InChiKey: GZKCUPAZXOGJIO-HZGWLXKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三丁基乙烯基锡 、 (R)-3-Acetoxymethyl-7-[1-bromo-meth-(E)-ylidene]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 tris(dibenzylideneacetone)dipalladium (0) 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 10.5h， 以80%的产率得到benzhydryl 7-[(E)-prop-2'-enylidene]cephalosporanate 1,1-dioxide
  参考文献：
  名称：

  Catalytic Approaches to the Synthesis of β-Lactamase Inhibitors

  摘要：

  Catalytic couplings were utilized to stereospecifically synthesize several 7E- and 7Z-alkylidenecephalosporins. Members of this class are known inhibitors of beta-lactamase. Zinc/NH4Cl reduction of dibromide 14 stereospecifically produced E-monobromide, 15. In contrast, treatment of 14 with isopropylmagnesium bromide, followed by mild acid, stereospecifically produced Z-monobromide 27. These reactions involves table, intermediate alpha-(metalloalkylidene)-beta-lactams. Monobromides 15 and 27 were stereo specific ally coupled to organostannanes, or were converted to the corresponding organostannanes, 22 and 32, which coupled with organohalides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00426-9

文献信息

• Stille coupling approaches to the stereospecific synthesis of 7-[(E)-alkylidene]cephalosporins
  作者：John D. Buynak、Venkata Ramana Doppalapudi、Mohammed Frotan、Ramon Kumar

  DOI：10.1016/s0040-4039(98)02691-4

  日期：1999.2

  Stills coupling methodology is used to stereospecifically synthesize 7-[(E)-alkylidene]cephalosporins, potential enzyme inhibitors which are unavailable via other synthetic methodology. Two procedures are described, utilizing either a stannylalkylidene cephem which is then coupled with an organohalide, or a haloalkylidene cephem which is coupled with an organostannane. (C) 1999 Elsevier Science Ltd. All rights reserved.