(E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methylhept-6-enal | 1615686-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methylhept-6-enal
• CAS: 1615686-86-6
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: LTPRNZGQBDGTSL-KPJVXMDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methylhept-6-enal 在 manganese(IV) oxide 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 38.17h， 生成 (S,E)-6-(6-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl)-2-methylhepta-1,6-dien-1-yl)-4-methyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of Aphadilactones A–D

  摘要：

  The first total synthesis of aphadilactones A-D, diastereomeric natural products recently isolated from the Meliaceae plant Aphanamixis grandifolia by Yue and co-workers, which possess an unprecedented carbon skeleton, has been achieved. The synthesis features a catalytic asymmetric hetero-Diels-Alder reaction to form the dihydropyran ring, concurrent installation of the lactone and furan moieties via a tandem acid-catalyzed acetal cleavage, oxidation, and cyclization process, and an intermolecular Diels-Alder reaction to forge the target products.

  DOI：

  10.1021/jo501117k
• 作为产物：
  描述：

  tert-butyl(((E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methylhept-6-en-1-yl)oxy)dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.17h， 生成 (E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methylhept-6-enal
  参考文献：
  名称：

  Total Synthesis of Aphadilactones A–D

  摘要：

  The first total synthesis of aphadilactones A-D, diastereomeric natural products recently isolated from the Meliaceae plant Aphanamixis grandifolia by Yue and co-workers, which possess an unprecedented carbon skeleton, has been achieved. The synthesis features a catalytic asymmetric hetero-Diels-Alder reaction to form the dihydropyran ring, concurrent installation of the lactone and furan moieties via a tandem acid-catalyzed acetal cleavage, oxidation, and cyclization process, and an intermolecular Diels-Alder reaction to forge the target products.

  DOI：

  10.1021/jo501117k