(+)-头孢菌素C | 97344-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (+)-头孢菌素C
• 英文名称: cephalosporolide C
• 英文别名: (4S,5S,10R)-4,5-dihydroxy-10-methyloxecane-2,7-dione
• CAS: 97344-02-0
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: JTOYXZZLKBAIEJ-YEPSODPASA-N

物化性质

• 熔点：
  82-84 °C
• 沸点：
  433.1±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-头孢菌素C 以 吡啶 为溶剂， 反应 0.08h， 生成 cephalosporolide B methanesulphonate
  参考文献：
  名称：

  Ackland, Mark J.; Hanson, James R.; Hitchcock, Peter B., Journal of the Chemical Society. Perkin transactions I, 1985, p. 843 - 848

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-cephalosporolide B 在 samarium diiodide 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 (+)-头孢菌素C
  参考文献：
  名称：

  Cephalosporolide B Serving as a Versatile Synthetic Precursor: Asymmetric Biomimetic Total Syntheses of Cephalosporolides C, E, F, G, and (4-OMe-)G

  摘要：

  Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

  DOI：

  10.1021/ol402913m

文献信息

• Structural Revision of Cephalosporolide J and Bassianolone
  作者：Liyan Song、Ka-Ho Lee、Zhenyang Lin、Rongbiao Tong

  DOI：10.1021/jo402602h

  日期：2014.2.7

  The NMR spectra for three "natural" products: cephalosporolide C (Ces-C), cephalosporolide J (Ces-J), and bassianolone were found to be identical, and we proposed that Ces-C was the correct structure for the reported spectra. The first total synthesis of the proposed structure for Ces-J was achieved to support our structural revision for Ces-J. Chemical transformations of bassianolone and computational prediction of C-13 NMR spectra allowed us to conclude that Ces-C was the correct structure for bassianolone. Our synthetic and computational studies suggested that these "different" natural products Ces-C, Ces-J, and bassianolone have the same structure: Ces-C.