4-(methoxymethyloxy)hex-5-en-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(methoxymethyloxy)hex-5-en-2-ol
• 英文别名: 4-(methoxymethoxy)hex-5-en-2-ol
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: HHWDEOGIJBAYTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(methoxymethyloxy)hex-5-en-2-ol 在 三乙烯二胺 、 盐酸 、 偶氮二异丁腈 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 131.5h， 生成 rac-(2S,3R,5S)-2-bromomethyl-5-methyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis and structural characterization of the isomuscarines

  摘要：

  Four diastereomers of 2-[(trimethylammonium)-methyl]-5-methyltetrahydrofuran-3-ol, trivially named isomuscarine, allo-isomuscarine, epi-isomuscarine, and epiallo-isomuscarine, were prepared as bromide salts from 2,4-like and 2,4-unlike diastereomers of 3-(4-hydroxyhex-5-en-2-oxy)-4-methylthiazole-2(3H)-thione. The strategy for constructing the tetrahydrofuran nucleus of the isomuscarines uses alkenoxyl radical 5-exo-bromocyclization, occurring 2,3-cis-selectively for the 2,4-like-4-hydroxyhex-5-en-2-oxyl radical, and 2,3-trans-selectively for the 2,4-unlike diastereomer. A fraction of 4hydroxyhex-5-en-2-oxyl radicals cyclizes 6-endo-selectively providing 5-bromo-2-methyltetrahydropyran-4-ols in yields between 3 and 15%. Substituting trimethylamine for bromide in 5-exo-bromocyclized products furnishes isomuscarine bromides, which were structurally characterized by X-ray diffraction and NMR-spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.085
• 作为产物：
  描述：

  4-羟基己-5-烯-2-酮 在 lithium aluminium tetrahydride 、 四磷十氧化物 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 19.5h， 生成 4-(methoxymethyloxy)hex-5-en-2-ol
  参考文献：
  名称：

  Synthesis and structural characterization of the isomuscarines

  摘要：

  Four diastereomers of 2-[(trimethylammonium)-methyl]-5-methyltetrahydrofuran-3-ol, trivially named isomuscarine, allo-isomuscarine, epi-isomuscarine, and epiallo-isomuscarine, were prepared as bromide salts from 2,4-like and 2,4-unlike diastereomers of 3-(4-hydroxyhex-5-en-2-oxy)-4-methylthiazole-2(3H)-thione. The strategy for constructing the tetrahydrofuran nucleus of the isomuscarines uses alkenoxyl radical 5-exo-bromocyclization, occurring 2,3-cis-selectively for the 2,4-like-4-hydroxyhex-5-en-2-oxyl radical, and 2,3-trans-selectively for the 2,4-unlike diastereomer. A fraction of 4hydroxyhex-5-en-2-oxyl radicals cyclizes 6-endo-selectively providing 5-bromo-2-methyltetrahydropyran-4-ols in yields between 3 and 15%. Substituting trimethylamine for bromide in 5-exo-bromocyclized products furnishes isomuscarine bromides, which were structurally characterized by X-ray diffraction and NMR-spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.085