6-<6-<3-<3-(acetyloxy)-2-methoxy-1-methylbutyl>-2-methyloxiranyl>-1,5-dimethyl-1,3-hexadienyl>tetrahydro-5-methyl-2H-pyran-2-acetic acid methyl ester | 144811-47-2

• 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-<3-(acetyloxy)-2-methoxy-1-methylbutyl>-2-methyloxiranyl>-1,5-dimethyl-1,3-hexadienyl>tetrahydro-5-methyl-2H-pyran-2-acetic acid methyl ester
• 英文别名: 6-(6-{3-[3-(acetyloxy)-2-methoxy-1-methylbutyl]-2-methyloxiranyl}-1,5-dimethyl-1,3-hexadienyl)tetrahydro-5-methyl-2H-pyran-2-acetic acid methyl ester
• CAS: 144811-47-2
• 化学式: C₂₈H₄₆O₇
• 分子量: 494.669
• InChiKey: NPSNUKYKXLTUSI-PWLAJAQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  83.59
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-<6-<3-<3-(acetyloxy)-2-methoxy-1-methylbutyl>-2-methyloxiranyl>-1,5-dimethyl-1,3-hexadienyl>tetrahydro-5-methyl-2H-pyran-2-acetic acid methyl ester 在 二甲基硫 、 臭氧 作用下， 生成 methyl 2-[(2S,5R,6R)-6-acetyl-5-methyloxan-2-yl]acetate 、 5-<4-(acetyloxy)-1-hydroxy-3-methoxy-2-methylpentyl>-dihydro-3,5-dimethyl-2-(3H)-furanone
  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
• 作为产物：
  描述：

  herboxidiene 在 吡啶 、 草酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 5.5h， 生成 6-<6-<3-<3-(acetyloxy)-2-methoxy-1-methylbutyl>-2-methyloxiranyl>-1,5-dimethyl-1,3-hexadienyl>tetrahydro-5-methyl-2H-pyran-2-acetic acid methyl ester
  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