trans-5,5-dimethyl-9-hydroxy-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c][1]benzopyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: trans-5,5-dimethyl-9-hydroxy-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c][1]benzopyran
• 英文别名: (4aS,10bS)-5,5-dimethyl-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]chromen-9-ol
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ZBJNGHVNVXGEOP-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2,5-二羟基苯甲醛 、 5-甲基-4-己烯-1-醇 在 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 苯 为溶剂， 反应 24.0h， 以84%的产率得到trans-5,5-dimethyl-9-hydroxy-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c][1]benzopyran
  参考文献：
  名称：

  Stereoselective Synthesis of Pyrano[3,2-c]benzopyrans via Intramolecular Cycloaddition of o-Quinonemethides Generated from Salicylaldehydes and Unsaturated Alcohols under Very Mild Conditions

  摘要：

  Intramolecular [4 + 2] cycloaddition reaction of 6-(4-alkenyloxymethylene)-2,4-cyclohexadien-1-ones generated from the reaction between substituted salicylaldehydes and unsaturated alcohols under mild conditions was investigated. In general, the reaction furnished tricyclic compounds containing the pyranobenzopyran skeleton with trans-fused B/C ring in very good yields (Tables 1 and 2). Furthermore, geometry of the olefinic bond of the starting material is retained during the reaction.

  DOI：

  10.1021/jo991132h

文献信息

• Stereoselective Synthesis of Pyrano[3,2-<i>c</i>]benzopyrans via Intramolecular Cycloaddition of <i>o</i>-Quinonemethides Generated from Salicylaldehydes and Unsaturated Alcohols under Very Mild Conditions
  作者：Hidekazu Miyazaki、Kiyoshi Honda、Masatoshi Asami、Seiichi Inoue

  DOI：10.1021/jo991132h

  日期：1999.12.1

  Intramolecular [4 + 2] cycloaddition reaction of 6-(4-alkenyloxymethylene)-2,4-cyclohexadien-1-ones generated from the reaction between substituted salicylaldehydes and unsaturated alcohols under mild conditions was investigated. In general, the reaction furnished tricyclic compounds containing the pyranobenzopyran skeleton with trans-fused B/C ring in very good yields (Tables 1 and 2). Furthermore, geometry of the olefinic bond of the starting material is retained during the reaction.