natriumnarasin | 58331-17-2

• 物质功能分类: 化学试剂 - 有机试剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: natriumnarasin
• 英文别名: naransin sodium；Narasin (sodium)；sodium;(2R)-2-[(2R,3S,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-3,5-dimethyloxan-2-yl]butanoate
• CAS: 58331-17-2
• 化学式: C₄₃H₇₁O₁₁*Na
• 分子量: 787.02
• InChiKey: NBRZEFXQRCTYMC-DAALJYCPSA-M

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  55
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  11

制备方法与用途

海南霉素是一种聚醚类抗生素，主要用于预防和治疗家禽球虫病，并作为牛、羊等家畜的饲用促生长剂。

反应信息

• 作为反应物：
  描述：

  natriumnarasin 在 甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以48%的产率得到α-ethyl-6-<5-ethyl-9-(2-furanyl)-2,6-dihydroxy-1,3,7-trimethyl-4-oxodecyl>tetrahydro-3,5-dimethyl-2H-pyran-2-acetic acid
  参考文献：
  名称：

  Novel degradation products from the treatment of salinomycin and narasin with formic acid

  摘要：

  Salinomycin and narasin (4-methylsalinomycin) upon treatment with HCO2H furnish the known furanone fragment 3 and the complementary but rearranged fragments 1 and 2 respectively. The structure of 1 has been established by X-ray analysis. Upon being heated under reflux in PhMe, 1 undergoes the retrograde aldol reaction to furnish alpha, gamma-dimethyl-2-furanbutanal (4). The furan moiety of 1 is more resistant to electrophilic substitution than expected, but it can be acylated by highly reactive reagents such as (CF3CO)2O and AcOSO2Me. Compounds 1 and 2, the acetyl and trifluoracetyl derivatives of the former, and the reduction products thereof have no significant anticoccidial activity.

  DOI：

  10.1021/jm00396a045

文献信息

• Novel degradation products from the treatment of salinomycin and narasin with formic acid
  作者：Jennie L. Wells、Jon Bordner、Paul Bowles、James W. McFarland

  DOI：10.1021/jm00396a045

  日期：1988.1

  Salinomycin and narasin (4-methylsalinomycin) upon treatment with HCO2H furnish the known furanone fragment 3 and the complementary but rearranged fragments 1 and 2 respectively. The structure of 1 has been established by X-ray analysis. Upon being heated under reflux in PhMe, 1 undergoes the retrograde aldol reaction to furnish alpha, gamma-dimethyl-2-furanbutanal (4). The furan moiety of 1 is more resistant to electrophilic substitution than expected, but it can be acylated by highly reactive reagents such as (CF3CO)2O and AcOSO2Me. Compounds 1 and 2, the acetyl and trifluoracetyl derivatives of the former, and the reduction products thereof have no significant anticoccidial activity.