(E)-8-hydroxy-6-methyl-6-octen-3-one tetrahydropyranyl ether | 458565-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-8-hydroxy-6-methyl-6-octen-3-one tetrahydropyranyl ether
• 英文别名: (E)-6-methyl-8-(tetrahydro-2H-pyran-2-yloxy)oct-6-en-3-one；(E)-6-methyl-8-(oxan-2-yloxy)oct-6-en-3-one
• CAS: 458565-92-9
• 化学式: C₁₄H₂₄O₃
• 分子量: 240.343
• InChiKey: YMNCBDFRYZWAQW-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  (E)-8-hydroxy-6-methyl-6-octen-3-one tetrahydropyranyl ether 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84%的产率得到(E)-8-hydroxy-6-methyl-6-octen-3-one
  参考文献：
  名称：

  一锅形成由仲胺形成的氮杂烯醇酸酯，然后缩合成酯和烷基溴化物

  摘要：

  从商业仲胺开始，一锅法允许通过一锅去质子化/氧化/原位再去质子化/酰化序列直接进入烯胺酮，而无需中间分离中间席夫碱或其相应的烯胺互变异构体。在酸性处理后，另一种涉及相似的氧化步骤然后进行一或两个烷基化步骤的一锅法序列，直接从母体胺得到官能化的酮。该方法已被应用于谷物叶甲虫Oulema melanopus雄性聚集信息素的快速合成。

  DOI：

  10.1016/j.tet.2012.04.105
• 作为产物：
  描述：

  (E)-6-hydroxy-4-methyl-4-hexenal tetrahydropyranyl ether 在 重铬酸吡啶 、 三氟乙酸吡啶 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (E)-8-hydroxy-6-methyl-6-octen-3-one tetrahydropyranyl ether
  参考文献：
  名称：

  Identification and Electrophysiological Activity of a Novel Hydroxy Ketone Emitted by Male Cereal Leaf Beetles

  摘要：

  Comparisons of collections of volatiles from male and female Oulema melanopus, feeding on host foliage (oats), revealed an electrophysiologically active male specific compound (E) 8 hydroxy 6 methyl 6 octen 3 one (7), which is a new natural product The structure of 7 was elucidated by spectroscopic and microchemical studies and confirmed by chemical synthesis Antennal electrophysiology showed the sensitive detection of 7 by both sexes, which is consistent with a male produced aggregation pheromone.

  DOI：

  10.1021/np020063q

文献信息

• One-pot formation of aza-enolates from secondary amines and condensation to esters and alkyl bromides
  作者：Alice Chevalley、Jean-Pierre Férézou

  DOI：10.1016/j.tet.2012.04.105

  日期：2012.7

  Starting from commercial secondary amines, a one-pot procedure allows a direct access to enaminones through a one-pot deprotonation/oxidation/in situ re-deprotonation/acylation sequence without intermediate isolation of the intermediate Schiff base or its corresponding enamine tautomer. An alternative one-pot sequence involving a similar oxidation step followed by one or two alkylation steps yields

  从商业仲胺开始，一锅法允许通过一锅去质子化/氧化/原位再去质子化/酰化序列直接进入烯胺酮，而无需中间分离中间席夫碱或其相应的烯胺互变异构体。在酸性处理后，另一种涉及相似的氧化步骤然后进行一或两个烷基化步骤的一锅法序列，直接从母体胺得到官能化的酮。该方法已被应用于谷物叶甲虫Oulema melanopus雄性聚集信息素的快速合成。
• Identification and Electrophysiological Activity of a Novel Hydroxy Ketone Emitted by Male Cereal Leaf Beetles
  作者：Allard A. Cossé、Robert J. Bartelt、Bruce W. Zilkowski

  DOI：10.1021/np020063q

  日期：2002.8.1

  Comparisons of collections of volatiles from male and female Oulema melanopus, feeding on host foliage (oats), revealed an electrophysiologically active male specific compound (E) 8 hydroxy 6 methyl 6 octen 3 one (7), which is a new natural product The structure of 7 was elucidated by spectroscopic and microchemical studies and confirmed by chemical synthesis Antennal electrophysiology showed the sensitive detection of 7 by both sexes, which is consistent with a male produced aggregation pheromone.