(E,E)-6-(hexa-2,4-dien-2-yl)-4-methoxy-3-methyl-2H-pyran-2-one | 1000777-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (E,E)-6-(hexa-2,4-dien-2-yl)-4-methoxy-3-methyl-2H-pyran-2-one
• 英文别名: 8,9-dehydroxylarone；6-[(2E,4E)-hexa-2,4-dien-2-yl]-4-methoxy-3-methylpyran-2-one
• CAS: 1000777-29-6
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: RDXUWZYDNPIQRO-SBIWHPGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-庚烷二酮 在 manganese(IV) oxide 、 selenium(IV) oxide 、 正丁基锂 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 49.0h， 生成 6-((2Z,4E)-hexa-2,4-dien-2-yl)-4-methoxy-3-methyl-2H-pyran-2-one 、 (E,E)-6-(hexa-2,4-dien-2-yl)-4-methoxy-3-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Total synthesis of infectopyrone, aplysiopsenes A–C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone

  摘要：

  The total synthesis of the 2-pyrone natural products nectriapyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, and of 8,9-dehydroxylarone were achieved by Wittig olefination starting with vermopyrone. Infectopyrone was synthesized by Horner-Wadsworth-Emmons reaction starting with phomapyrone D. Racemic phomapyrone C methyl ether was obtained by hydrogenation of nectriapyrone. The total syntheses were achieved starting from commercially available 3,5-heptanedione and led to the desired natural products in 18-46% over 5-6 steps, whereupon all five-step syntheses were carried out with a single chromatographic workup. The total synthesis of infectopyrone, aplysiopsenes A-D, of phomapyrones A and D, and of 8,9-dehydroxylarone were achieved for the first time, giving unambiguous proof for the proposed structures of these natural products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.104

文献信息

• Total synthesis of infectopyrone, aplysiopsenes A–C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone
  作者：Oliver Geiseler、Joachim Podlech

  DOI：10.1016/j.tet.2012.06.104

  日期：2012.9

  The total synthesis of the 2-pyrone natural products nectriapyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, and of 8,9-dehydroxylarone were achieved by Wittig olefination starting with vermopyrone. Infectopyrone was synthesized by Horner-Wadsworth-Emmons reaction starting with phomapyrone D. Racemic phomapyrone C methyl ether was obtained by hydrogenation of nectriapyrone. The total syntheses were achieved starting from commercially available 3,5-heptanedione and led to the desired natural products in 18-46% over 5-6 steps, whereupon all five-step syntheses were carried out with a single chromatographic workup. The total synthesis of infectopyrone, aplysiopsenes A-D, of phomapyrones A and D, and of 8,9-dehydroxylarone were achieved for the first time, giving unambiguous proof for the proposed structures of these natural products. (C) 2012 Elsevier Ltd. All rights reserved.