(6RS,2'SR)-6-(5-methyl-3-hexyn-5-en-2-oxy)-2,3-dihydro-6H-pyran-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (6RS,2'SR)-6-(5-methyl-3-hexyn-5-en-2-oxy)-2,3-dihydro-6H-pyran-3-one
• 英文别名: (2R)-2-[(2R)-5-methylhex-5-en-3-yn-2-yl]oxy-2H-pyran-5-one
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: LVJMRLWLEKBBAT-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6RS,2'SR)-6-(5-methyl-3-hexyn-5-en-2-oxy)-2,3-dihydro-6H-pyran-3-one 在 zinc chloride diethyl ether 作用下， 以 1,2-二氯乙烷 为溶剂， 以72%的产率得到(1RS,3SR,8SR,12SR)-3-methyl-6-methylene-2,11-dioxatricyclo<6.3.1.0^4,12>dodec-4-en-9-one
  参考文献：
  名称：

  The intramolecular enyne diels-alder reaction. Stereoselective construction of tricyclic dioxadienones and mechanistic outline

  摘要：

  4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H pyran 3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides. A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.

  DOI：

  10.1016/s0040-4020(01)91218-9
• 作为产物：
  描述：

  (3-methyl-but-3-en-1-ynyl)-lithium 在 zinc chloride diethyl ether 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (6RS,2'SR)-6-(5-methyl-3-hexyn-5-en-2-oxy)-2,3-dihydro-6H-pyran-3-one
  参考文献：
  名称：

  The intramolecular enyne diels-alder reaction. Stereoselective construction of tricyclic dioxadienones and mechanistic outline

  摘要：

  4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H pyran 3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides. A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.

  DOI：

  10.1016/s0040-4020(01)91218-9

文献信息

• The intramolecular enyne diels-alder reaction. Stereoselective construction of tricyclic dioxadienones and mechanistic outline
  作者：H.M.R. Hoffmann、D. Krumwiede、B. Mucha、H.H. Oehlerking、G.W. Prahst

  DOI：10.1016/s0040-4020(01)91218-9

  日期：1993.1

  4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H pyran 3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides. A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.