(5R,6S)-6-((R)-1-tert-hydroxyethyl)-2-(tetrahydro-3-furylmethyl)penem-3-carboxylic acid allyl ester | 117422-98-7

• 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: (5R,6S)-6-((R)-1-tert-hydroxyethyl)-2-(tetrahydro-3-furylmethyl)penem-3-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(oxolan-3-ylmethyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 117422-98-7
• 化学式: C₁₆H₂₁NO₅S
• 分子量: 339.412
• InChiKey: ODXMIADQYTZXKG-BTDLXYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5R,6S)-6-((R)-1-tert-hydroxyethyl)-2-(tetrahydro-3-furylmethyl)penem-3-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 三苯基膦 、 sodium 2-ethylhexanoic acid 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (5R,6S)-6-((R)-1-tert-hydroxyethyl)-2-(tetrahydro-3-furylmethyl)penem-3-carboxylic acid sodium salt 、 (5R,6S)-6-((R)-1-tert-hydroxyethyl)-2-((R)-tetrahydro-3-furylmethyl)penem-3-carboxylic acid sodium salt
  参考文献：
  名称：

  Structure-activity relationships of penem antibiotics: Crystallographic structures and implications for their antimicrobial activities

  摘要：

  Twelve closely related crystal structures of the penem derivatives revealed a characteristic short contact of the oxygen atom in the C2 side-chains with the S1 atom. The side-chain conformations of the crystal structures showed a good correlation with the antimicrobial activity. In particular, the penems which show high antimicrobial activity have similar torsion angles for S1-C2-C1'-C2', suggesting that the disposition of the C2' atom would be important for binding to penicillin-interacting enzymes. Two conformations of the C6 hydroxyethyl group were observed in the crystal structures. Of those two, the conformation with a larger torsion angle (delta = 179.2 degrees) is deduced to be the enzyme-bound conformation in the Michaelis complex. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00073-4
• 作为产物：
  描述：

  草酰氯单烯丙酯 在 四丁基氟化铵 、 溶剂黄146 、 三乙胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 xylene 为溶剂， 反应 19.67h， 生成 (5R,6S)-6-((R)-1-tert-hydroxyethyl)-2-(tetrahydro-3-furylmethyl)penem-3-carboxylic acid allyl ester
  参考文献：
  名称：

  Structure-activity relationships of penem antibiotics: Crystallographic structures and implications for their antimicrobial activities

  摘要：

  Twelve closely related crystal structures of the penem derivatives revealed a characteristic short contact of the oxygen atom in the C2 side-chains with the S1 atom. The side-chain conformations of the crystal structures showed a good correlation with the antimicrobial activity. In particular, the penems which show high antimicrobial activity have similar torsion angles for S1-C2-C1'-C2', suggesting that the disposition of the C2' atom would be important for binding to penicillin-interacting enzymes. Two conformations of the C6 hydroxyethyl group were observed in the crystal structures. Of those two, the conformation with a larger torsion angle (delta = 179.2 degrees) is deduced to be the enzyme-bound conformation in the Michaelis complex. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00073-4