(5R,6S)-6-((R)-1-hydroxyethyl)-2-((S)-tetrahydro-2-furyl)penem-3-carboxylic acid allyl ester | 106559-79-9

• 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-hydroxyethyl)-2-((S)-tetrahydro-2-furyl)penem-3-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2S)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 106559-79-9
• 化学式: C₁₅H₁₉NO₅S
• 分子量: 325.386
• InChiKey: KDUOTWOTIWSCEX-MAGOMRGPSA-N

物化性质

• 沸点：
  553.4±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 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-hydroxyethyl)-2-((S)-tetrahydro-2-furyl)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-hydroxyethyl)-2-((S)-tetrahydro-2-furyl)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-hydroxyethyl)-2-((S)-tetrahydro-2-furyl)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

文献信息

• Structure of penem sulphoxide
  作者：Rie Tanaka、Yoshiaki Oyama、Masaji Ishiguro

  DOI：10.1039/c39900000853

  日期：——

  Oxidation of the penem derivative (1a,b) by m-chloroperbenzoic acid occurs by the direction of the β-lactam carbonyl oxygen to give β-sulphoxide (2a,b) as a major product, whose structure has been determined by X-ray crystallography.

  青霉烯衍生物（氧化1A，b通过）米氯过苯甲酸发生由β内酰胺羰基的氧，得到β亚砜（所述方向图2a，b）作为主要产物，其结构已被确定X射线晶体学。
• TANAKA, RIE;OYAMA, YOSHIAKI;ISHIGURO, MASAJI, J. CHEM. SOC. CHEM. COMMUN.,(1990) N2, C. 853-854
  作者：TANAKA, RIE、OYAMA, YOSHIAKI、ISHIGURO, MASAJI

  DOI：——

  日期：——
• ISIGURO, MASADZI;IVATA, XIROMITSU;NAKADZUKA, TAKASI
  作者：ISIGURO, MASADZI、IVATA, XIROMITSU、NAKADZUKA, TAKASI

  DOI：——

  日期：——