aphadilactone A | 1522004-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: aphadilactone A
• 英文别名: (4S,7R)-4-(5,5-dimethyl-4-oxofuran-2-yl)-2,2-dimethyl-4,7-bis[(E)-4-methyl-5-[(2S)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]pent-4-enyl]-6,7-dihydro-5H-1-benzofuran-3-one
• CAS: 1522004-66-5
• 化学式: C₄₀H₅₂O₈
• 分子量: 660.848
• InChiKey: ZFQFRRMVMSIOAK-MKUYYVDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methyl-2-methylenehept-6-enal 在 manganese(IV) oxide 、 2,6-二叔丁基-4-甲基苯酚 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 45.17h， 生成 aphadilactone A 、 aphadilactone B 、 aphadilactone C 、 aphadilactone D
  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

文献信息

• Total Synthesis of Aphadilactones A–D
  作者：Jian-Peng Yin、Min Gu、Ying Li、Fa-Jun Nan

  DOI：10.1021/jo501117k

  日期：2014.7.3

  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.