2-(iodomethyl)-5-pentadecyl-1,4-dioxane | 81861-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-(iodomethyl)-5-pentadecyl-1,4-dioxane
• CAS: 81861-45-2
• 化学式: C₂₀H₃₉IO₂
• 分子量: 438.433
• InChiKey: IXSWIQDSXKIEIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  23.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(iodomethyl)-5-pentadecyl-1,4-dioxane 在 盐酸 作用下， 以 氯仿 、 苯 为溶剂， 反应 25.5h， 生成 2-(hydroxymethyl)-5-pentadecyl-1,4-dioxane monosodium phosphate
  参考文献：
  名称：

  Darmstoff analogs. 2. Ring and side chain effects on smooth muscle contraction

  摘要：

  2-cis-delta 8-Heptadecenyl-4-(hydroxymethyl)-1,3-dioxolane monosodium phosphate (1b) has been shown to be present as a major component of Darmstoff in mammalian intestine and to be a potent inducer for contraction of intestinal smooth muscle. The analogous 2-pentadecyl material 1a, also found abundantly in the intestine, is inactive. In this study, synthesis of phosphorylated hydroxymethyl-1,4-dioxanes, -tetrahydrofurans, -cyclopentanes, and -oxathiolanes bearing both oleyl and palmityl side chains is reported. Of these, 2-(hydroxymethyl)-5-cis-delta 8-heptadecenyl-1,4-dioxane monosodium phosphate (2b) exhibits about 12% of the activity of 1b. Its pentadecyl analogue 2a, like 1a, is totally inactive, as are all other compounds prepared. The results indicate that Darmstoff-like compounds exhibit specific chemical requirements for activity and that where activity is encountered, the side-chain specificity noted in 1a and 1b can be preserved.

  DOI：

  10.1021/jm00344a006
• 作为产物：
  描述：

  2-Allyloxy-heptadecan-1-ol 在 碘 、 potassium carbonate 作用下， 以 乙醚 、 水 为溶剂， 生成 2-(iodomethyl)-5-pentadecyl-1,4-dioxane
  参考文献：
  名称：

  Darmstoff analogs. 2. Ring and side chain effects on smooth muscle contraction

  摘要：

  2-cis-delta 8-Heptadecenyl-4-(hydroxymethyl)-1,3-dioxolane monosodium phosphate (1b) has been shown to be present as a major component of Darmstoff in mammalian intestine and to be a potent inducer for contraction of intestinal smooth muscle. The analogous 2-pentadecyl material 1a, also found abundantly in the intestine, is inactive. In this study, synthesis of phosphorylated hydroxymethyl-1,4-dioxanes, -tetrahydrofurans, -cyclopentanes, and -oxathiolanes bearing both oleyl and palmityl side chains is reported. Of these, 2-(hydroxymethyl)-5-cis-delta 8-heptadecenyl-1,4-dioxane monosodium phosphate (2b) exhibits about 12% of the activity of 1b. Its pentadecyl analogue 2a, like 1a, is totally inactive, as are all other compounds prepared. The results indicate that Darmstoff-like compounds exhibit specific chemical requirements for activity and that where activity is encountered, the side-chain specificity noted in 1a and 1b can be preserved.

  DOI：

  10.1021/jm00344a006