(+/-)-1-(3',4'-diacetoxyphenyl)but-3-en-1-ol | 406486-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (+/-)-1-(3',4'-diacetoxyphenyl)but-3-en-1-ol
• 英文别名: [2-Acetyloxy-4-(1-hydroxybut-3-enyl)phenyl] acetate
• CAS: 406486-82-6
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: RJKNCKVLXRGMHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 丙醛 、 (+/-)-1-(3',4'-diacetoxyphenyl)but-3-en-1-ol 在 三甲基硅乙酸酯 、 三氟化硼乙醚 作用下， 以 环己烷 为溶剂， 反应 1.0h， 以67%的产率得到4β-acetoxy-2β-(3',4'-diacetoxyphenyl)-6β-ethyl-tetrahydropyran
  参考文献：
  名称：

  Oxonia-Cope Rearrangement and Side-Chain Exchange in the Prins Cyclization

  摘要：

  [GRAPHICS]Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.

  DOI：

  10.1021/ol0102850
• 作为产物：
  描述：

  丙烯酰碘 、 3,4-二乙酰氧基苯甲醛 在 indium 作用下， 以 水 为溶剂， 反应 48.0h， 以92%的产率得到(+/-)-1-(3',4'-diacetoxyphenyl)but-3-en-1-ol
  参考文献：
  名称：

  Oxonia-Cope Rearrangement and Side-Chain Exchange in the Prins Cyclization

  摘要：

  [GRAPHICS]Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.

  DOI：

  10.1021/ol0102850

文献信息

• Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans
  作者：Conor S. Barry、Nick Bushby、John R. Harding、Rachael A. Hughes、Gregory D. Parker、Richard Roe、Christine L. Willis

  DOI：10.1039/b504562b

  日期：——

  Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.

  用碳基亲核试剂在Prins环化途径上捕集中间体，可以进一步深入了解影响酸介导的均丙醇与醛反应的因素，从而可以设计出有效合成4-羟基-2,6-二取代四氢吡喃的化合物。
• Oxonia-Cope Rearrangement and Side-Chain Exchange in the Prins Cyclization
  作者：Stuart R. Crosby、John R. Harding、Clare D. King、Gregory D. Parker、Christine L. Willis

  DOI：10.1021/ol0102850

  日期：2002.2.1

  [GRAPHICS]Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.