allyl 6α-ethynyl-6β-hydroxypenicillinate | 147486-81-5

• 英文名称: allyl 6α-ethynyl-6β-hydroxypenicillinate
• 英文别名: prop-2-enyl (2S,5R,6R)-6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 147486-81-5
• 化学式: C₁₃H₁₅NO₄S
• 分子量: 281.332
• InChiKey: FFVOYMLWZKAJDI-RLCGTCKNSA-N

物化性质

• 沸点：
  441.4±45.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 allyl 6α-ethynyl-6β-hydroxypenicillinate 在 吡啶 作用下， 以 氯仿 为溶剂， 以61%的产率得到allyl 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
• 作为产物：
  描述：

  allyl 6α-hydroxypenicillinate 在 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 allyl 6α-ethynyl-6β-hydroxypenicillinate
  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