benzyl 6α-ethynyl-6β-(trifluoromethanesulfonato)penicillinate | 121534-38-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 6α-ethynyl-6β-(trifluoromethanesulfonato)penicillinate
• 英文别名: benzyl (2S,5R,6R)-6-ethynyl-3,3-dimethyl-7-oxo-6-(trifluoromethylsulfonyloxy)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 121534-38-1
• 化学式: C₁₈H₁₆F₃NO₆S₂
• 分子量: 463.455
• InChiKey: TUXNUOLDMBSZJV-XGWLTEMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 6α-ethynyl-6β-(trifluoromethanesulfonato)penicillinate 在 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以41%的产率得到benzyl 6α-(bromovinylidene)penicillinate
  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：

  6-oxopenicillanic acid benzyl ester 在 吡啶 作用下， 以 氯仿 为溶剂， 生成 benzyl 6α-ethynyl-6β-(trifluoromethanesulfonato)penicillinate
  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

文献信息

• The preparation of the first α-vinylidenepenams
  作者：John D. Buynak、H.B. Borate、Chad Husting、Trace Hurd、Jyoti Vallabh、Jacob Matthew、Jarvis Lambert、Upali Siriwardane

  DOI：10.1016/s0040-4039(00)80677-2

  日期：1988.1

  Benzyl esters of the first 6-vinylidenepenams have been prepared by reaction of 6-position propargylic triflates with higher order organocuprates. This methodology permits a great deal of versatility in the introduction of substituents at the terminal allenyl position.

  通过使6-位炔丙基三氟甲磺酸酯与更高阶的有机铜酸酯反应，制得了第一个6-亚乙烯基亚胺的苄基酯。这种方法在末端烯基位置引入取代基具有很大的通用性。
• BUYNAK, JOHN D.;BORATE, H. B.;HUSTING, CHAD;HURD, TRACE;VALLABH, JYOTI;MA+, TETRAHEDRON LETT., 29,(1988) N 40, C. 5033-5056
  作者：BUYNAK, JOHN D.、BORATE, H. B.、HUSTING, CHAD、HURD, TRACE、VALLABH, JYOTI、MA+

  DOI：——

  日期：——