2-(furan-2-yl)-3-isopropenyl-6-methyltetrahydropyran

• 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: 2-(furan-2-yl)-3-isopropenyl-6-methyltetrahydropyran
• 英文别名: 2-furan-2-yl-3-isopropenyl-6-methyltetrahydropyran；(2S,3R,6S)-2-(furan-2-yl)-6-methyl-3-prop-1-en-2-yloxane
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: CDIMEDCMRZNKAK-LOWVWBTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  糠醛 、 6-甲基-5-庚烯-2-醇 在 In(OSO₂CF₃)3 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到2-(furan-2-yl)-3-isopropenyl-6-methyltetrahydropyran
  参考文献：
  名称：

  Diverse Cyclization Catalyzed by In(OTf)₃ for the Convergent Assembly of Substituted Tetrahydrofurans and Tetrahydropyrans

  摘要：

  [GRAPHICS]A novel In(OTf)(3)-catalyzed (3,5) oxonium-ene type cyclization for the facile construction of various multisubstituted tetrahydrofurans and tetrahydropyrans was successfully developed. Further mechanistic investigations unveiled an ln(OTf)(3)-catalyzed skeletal reorganization of the tetrahydrofuran to its thermodynamic isomer under thermal conditions.

  DOI：

  10.1021/ol016228o

文献信息

• Diverse Cyclization Catalyzed by In(OTf)₃ for the Convergent Assembly of Substituted Tetrahydrofurans and Tetrahydropyrans
  作者：Teck-Peng Loh、Qi-Ying Hu、Kui-Thong Tan、Hin-Soon Cheng

  DOI：10.1021/ol016228o

  日期：2001.8.1

  [GRAPHICS]A novel In(OTf)(3)-catalyzed (3,5) oxonium-ene type cyclization for the facile construction of various multisubstituted tetrahydrofurans and tetrahydropyrans was successfully developed. Further mechanistic investigations unveiled an ln(OTf)(3)-catalyzed skeletal reorganization of the tetrahydrofuran to its thermodynamic isomer under thermal conditions.
• A simple and expeditious synthesis of 2,3,6-trisubstituted tetrahydropyrans through (3,5)-oxonium-ene cyclization using molecular iodine
  作者：N. Prudhvi Raju、B. Jagan Mohan Reddy、R. Anjibabu、K. Muralikrishna、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2013.04.104

  日期：2013.7

  A variety of aldehydes undergo a smooth coupling with 6-methylhept-5-en-2ol in the presence of molecular iodine to afford the 2,3,6-trisubstituted tetrahydropyrans in good yields through 3,5-oxonium-ene cyclization under mild and neutral conditions. This method is simple, convenient, and cost-effective. (C) 2013 Elsevier Ltd. All rights reserved.