-1-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-2-methyl-4,6-octadien-3-one | 149403-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: -1-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-2-methyl-4,6-octadien-3-one
• 英文别名: (2R,4E,6E)-1-[(3S,6R)-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]-2-methylocta-4,6-dien-3-one
• CAS: 149403-43-0
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: OSCUIGRKMGWNOB-JUFKYBKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  -1-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-2-methyl-4,6-octadien-3-one 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 Acetic acid (3S,6R)-6-{(4E,6E)-(R)-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methyl-octa-4,6-dienyl}-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Stereocontrolled routes to functionalized [1,8-bc]naphthopyran. A study on the total synthesis of quassinoids and tetrahydronaphthalene antibiotics

  摘要：

  The intramolecular Diels-Alder reactions of (4E,6E)-1-(5,6-dihydro-5-oxo-2H-pyran-2-yl)-2-methyl-4,6-octadienes have been examined with a planned synthesis of quassinoids, chlorotricholides, and mevinic acids. The intramolecular Diels-Alder reactions of 1-(5-oxo-2H-pyran-2-yl)-2-methylocta-4,6-dien-3-ones preferentially afforded products possessing a trans-ring junction. For 1-(2H-pyran-2-yl)-2-methyl-3-[(thexyklimethylsilyl)oxy]-4,6-octadienes the cyclization was controlled by the methyl at C-2 and led to cis-fused or trans-fused derivatives. The reactions were performed under thermal Lewis acid catalyzed and sonochemical conditions with no changes in the reaction selectivity and reaction yields. However, IMDA of 10b in the presence of silica gel produced a dramatic change in the course of the reaction.

  DOI：

  10.1021/jo00067a027
• 作为产物：
  描述：

  -4-(5,6-Dihydro-5-<(trimethylsilyl)oxy>-2H-pyran-2-yl)-3-methyl-2-butanone 在 柠檬酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 -1-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-2-methyl-4,6-octadien-3-one
  参考文献：
  名称：

  Stereocontrolled routes to functionalized [1,8-bc]naphthopyran. A study on the total synthesis of quassinoids and tetrahydronaphthalene antibiotics

  摘要：

  The intramolecular Diels-Alder reactions of (4E,6E)-1-(5,6-dihydro-5-oxo-2H-pyran-2-yl)-2-methyl-4,6-octadienes have been examined with a planned synthesis of quassinoids, chlorotricholides, and mevinic acids. The intramolecular Diels-Alder reactions of 1-(5-oxo-2H-pyran-2-yl)-2-methylocta-4,6-dien-3-ones preferentially afforded products possessing a trans-ring junction. For 1-(2H-pyran-2-yl)-2-methyl-3-[(thexyklimethylsilyl)oxy]-4,6-octadienes the cyclization was controlled by the methyl at C-2 and led to cis-fused or trans-fused derivatives. The reactions were performed under thermal Lewis acid catalyzed and sonochemical conditions with no changes in the reaction selectivity and reaction yields. However, IMDA of 10b in the presence of silica gel produced a dramatic change in the course of the reaction.

  DOI：

  10.1021/jo00067a027