(2E)-5-(((4-methoxybenzyl)oxy)methyl)hexa-2,5-dien-1-ol | 1374123-33-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E)-5-(((4-methoxybenzyl)oxy)methyl)hexa-2,5-dien-1-ol
• 英文别名: (2E)-5-[(4-methoxyphenyl)methoxymethyl]hexa-2,5-dien-1-ol
• CAS: 1374123-33-7
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: QQKOICWHARQXAV-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chloromethyl-3-(p-methoxybenzyloxy)prop-1-ene 在 chromium dichloride 、 盐酸 、 copper(l) iodide 、 potassium carbonate 、 sodium sulfate 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 528.0h， 生成 (2E)-5-(((4-methoxybenzyl)oxy)methyl)hexa-2,5-dien-1-ol
  参考文献：
  名称：

  Exploratory studies toward the synthesis of the peroxylactone unit of plakortolides

  摘要：

  Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of beta-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the epoxide function. By this route, an advanced intermediate of plakortolides was obtained in six steps and 35% overall yield. The second approach featured a 1,2-dioxane ring forming by a double opening of bis-epoxides by ethereal hydrogen peroxide. This reaction did not proceed in the expected sense and exclusive formation of hydroperoxy tetrahydropyran derivatives was observed via a tandem oxacyclization-hydroperoxidation sequence. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.024

文献信息

• Exploratory studies toward the synthesis of the peroxylactone unit of plakortolides
  作者：Bogdan Barnych、Jean-Michel Vatèle

  DOI：10.1016/j.tet.2012.03.024

  日期：2012.5

  Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of beta-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the epoxide function. By this route, an advanced intermediate of plakortolides was obtained in six steps and 35% overall yield. The second approach featured a 1,2-dioxane ring forming by a double opening of bis-epoxides by ethereal hydrogen peroxide. This reaction did not proceed in the expected sense and exclusive formation of hydroperoxy tetrahydropyran derivatives was observed via a tandem oxacyclization-hydroperoxidation sequence. (C) 2012 Elsevier Ltd. All rights reserved.