benzhydryl 6-vinylidenepenicillinate | 127626-87-3

• 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 6-vinylidenepenicillinate
• CAS: 127626-87-3
• 化学式: C₂₃H₂₁NO₃S
• 分子量: 391.491
• InChiKey: UYTCKGSOKNFAQR-PZJWPPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzhydryl 6-vinylidenepenicillinate 在 三氯化铝 作用下， 以 二氯甲烷 、 硝基苯 为溶剂， 反应 0.17h， 以50%的产率得到6-vinylidenepenicillanic acid
  参考文献：
  名称：

  Synthesis of 6-vinylidenepenams

  摘要：

  The preparation of unique penicillin derivatives containing an exocyclic allene at the 6 position (6-vinylidenepenams) is described. The synthetic scheme utilizes 6-oxopenicillinates as intermediates which stereospecifically add acetylide anions forming propargylic alcohols. Displacement of the corresponding propargylic triflates with higher order cuprate reagents and with copper(I) halides proceeds rapidly and stereospecifically. Halogen-metal exchange of the 6-(halovinylidene)penams is described. The derived allenyl anions can be trapped by electrophiles. Conversion of selected allyl and benzhydryl esters to the corresponding carboxylic acids is described. The beta-lactamase inhibitory activity of the 6-(tert-butylvinylidene)penam sulfone is documented.

  DOI：

  10.1021/jo00058a008
• 作为产物：
  描述：

  benzhydryl 6-(α-iodovinylidene)penicillinate 在 甲基溴化镁 作用下， 以62%的产率得到benzhydryl 6-vinylidenepenicillinate
  参考文献：
  名称：

  金属-6-亚乙烯基戊烷的制备和用途

  摘要：

  母体未取代的6-亚乙烯基亚戊酰胺和各种6-炔基戊烯可从相应的烯丙基碘中获得。

  DOI：

  10.1039/c39900000294

文献信息

• The preparation and use of metallo-6-vinylidene penams
  作者：John D. Buynak、H. B. Borate、Grady Lamb、Harold Isom、Chad Husting、Dipti Khasnis

  DOI：10.1039/c39900000294

  日期：——

  The parent unsubstituted 6-vinylidenepenam and various 6-acetylenic penams are shown to be available from corresponding allenyl iodides.

  母体未取代的6-亚乙烯基亚戊酰胺和各种6-炔基戊烯可从相应的烯丙基碘中获得。
• BUYNAK, JOHN D.;BORATE, H. B.;LAMB, GRADY;ISORN, HAROLD;HUSTING, CHAD;KHA+, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 294-296
  作者：BUYNAK, JOHN D.、BORATE, H. B.、LAMB, GRADY、ISORN, HAROLD、HUSTING, CHAD、KHA+

  DOI：——

  日期：——
• Synthesis of 6-vinylidenepenams
  作者：John D. Buynak、H. B. Borate、Grady W. Lamb、Dipti D. Khasnis、Chad Husting、Harold Isom、Upali Siriwardane

  DOI：10.1021/jo00058a008

  日期：1993.3

  The preparation of unique penicillin derivatives containing an exocyclic allene at the 6 position (6-vinylidenepenams) is described. The synthetic scheme utilizes 6-oxopenicillinates as intermediates which stereospecifically add acetylide anions forming propargylic alcohols. Displacement of the corresponding propargylic triflates with higher order cuprate reagents and with copper(I) halides proceeds rapidly and stereospecifically. Halogen-metal exchange of the 6-(halovinylidene)penams is described. The derived allenyl anions can be trapped by electrophiles. Conversion of selected allyl and benzhydryl esters to the corresponding carboxylic acids is described. The beta-lactamase inhibitory activity of the 6-(tert-butylvinylidene)penam sulfone is documented.