6-<6-<3-(1-carboxyethyl)-2-methyloxiranyl>-1,5-dimethyl-1,3-hexadienyl>tetrahydro-5-methyl-2H-pyran-2-acetic acid | 144811-40-5

• 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: 6-<6-<3-(1-carboxyethyl)-2-methyloxiranyl>-1,5-dimethyl-1,3-hexadienyl>tetrahydro-5-methyl-2H-pyran-2-acetic acid
• 英文别名: 6-{6-[3-(1-carboxyethyl)-2-methyloxiranyl]-1,5-dimethyl-1,3-hexadienyl}tetrahydro-5-methyl-2H-pyran-2-acetic acid
• CAS: 144811-40-5
• 化学式: C₂₂H₃₄O₆
• 分子量: 394.508
• InChiKey: JUPQSDUAUKMSNQ-VKSQELJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  96.36
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  herboxidiene 在 jones reagent 作用下， 以 丙酮 为溶剂， 以37%的产率得到tetrahydro-6-<6-<3-(2-methoxy-1-methyl-3-oxobutyl)-2-methyloxiranyl>-1,5-dimethyl-1,3-hexadienyl>-5-methyl-2H-pyran-2-acetic acid
  参考文献：
  名称：

  Herboxidiene: a potent phytotoxic polyketide from Streptomyces sp. A7847

  摘要：

  Investigation of a secondary metabolite produced by Streptomyces sp. A7847 (ATCC 49982) has resulted in the identification of herboxidiene (1, C25H42O6), a novel polyketide with exceptional phytotoxicity to several annual weed species. Synthetic modification studies have defined the permissible structural alternations of 1 which maintain biological activity. Significant structural change (see compounds 12 and 13) resulted in a loss of activity as did opening of the epoxide ring (we compounds 5-8) or oxidation of the secondary alcohol at carbon 18 (3).

  DOI：

  10.1021/jo00052a042