methyl <2,3-13C2>-3-oxo-7-methyloctanoate | 137570-38-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl <2,3-13C2>-3-oxo-7-methyloctanoate
• 英文别名: methyl 7-methyl-3-oxo(2,3-13C2)octanoate
• CAS: 137570-38-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 188.229
• InChiKey: BDBSDNUYCZOLGA-VEJAREIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl <2,3-13C2>-3-oxo-7-methyloctanoate 在 potassium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 121.0h， 生成 <2,3-13C2>-3-oxo-7-methyloctanoic acid N-acetylcysteamine thioester
  参考文献：
  名称：

  Biosynthesis of virginiae butanolide A, a butyrolactone autoregulator from Streptomyces

  摘要：

  Virginiae butanolide A (VB A) (3) is one of the virginiamycin-inducing factors from Streptomyces virginiae and has a unique 2,3-disubstituted butanolide skeleton which is common to other signal molecules in Streptomyces. The biosynthesis of 3 in Streptomyces antibioticus, a high producer of 3, was studied by experiments with labeled precursors. C-13 and H-2 NMR results as well as CI-MS analyses of dibenzoate samples indicated that the probable biosynthetic pathway to 3 involved coupling between a beta-keto acid derivative and a C3 unit from glycerol, such as dihydroxyacetone or a derivative.

  DOI：

  10.1021/ja00028a037
• 作为产物：
  描述：

  <1-13C>-5-methylhexanenitrile 、 methyl (2-13C)bromoacetate 在 硼酸三甲酯 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以43.3%的产率得到methyl <2,3-13C2>-3-oxo-7-methyloctanoate
  参考文献：
  名称：

  Biosynthesis of virginiae butanolide A, a butyrolactone autoregulator from Streptomyces

  摘要：

  Virginiae butanolide A (VB A) (3) is one of the virginiamycin-inducing factors from Streptomyces virginiae and has a unique 2,3-disubstituted butanolide skeleton which is common to other signal molecules in Streptomyces. The biosynthesis of 3 in Streptomyces antibioticus, a high producer of 3, was studied by experiments with labeled precursors. C-13 and H-2 NMR results as well as CI-MS analyses of dibenzoate samples indicated that the probable biosynthetic pathway to 3 involved coupling between a beta-keto acid derivative and a C3 unit from glycerol, such as dihydroxyacetone or a derivative.

  DOI：

  10.1021/ja00028a037