(1SR)-1-((2RS,3SR)-2-(2-bromophenyl)tetrahydro-2H-pyran-3-yl)-1,3-dihydroisobenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (1SR)-1-((2RS,3SR)-2-(2-bromophenyl)tetrahydro-2H-pyran-3-yl)-1,3-dihydroisobenzofuran
• 英文别名: (1S)-1-[(2R,3S)-2-(2-bromophenyl)oxan-3-yl]-1,3-dihydro-2-benzofuran
• 化学式: C₁₉H₁₉BrO₂
• 分子量: 359.263
• InChiKey: XQDCYCRWKVBUQL-UHOSZYNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(5-hydroxypent-1-yn-1-yl)benzaldehyde 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1SR)-1-((2RS,3SR)-2-(2-bromophenyl)tetrahydro-2H-pyran-3-yl)-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  BF3·OEt2-catalyzed synthesis of 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran and trans-fused hexahydropyrano[3,2-c]chromene derivatives

  摘要：

  A novel intramolecular Prins cyclization of (E)-5-(2-(hydroxymethyl)phenyl)pent-4-en-1-ol with aldehydes has been achieved using 10 mol % BF3 center dot Et2O to produce 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran derivatives in good to excellent yields with high selectivity. Similar type of coupling with salicylaldehydes provides the trans-fused hexahydropyrano[3,2-c]chromene derivatives in excellent yields. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.05.083

文献信息

• BF3·OEt2-catalyzed synthesis of 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran and trans-fused hexahydropyrano[3,2-c]chromene derivatives
  作者：Ch. Syama Sundar、M. Ramana Reddy、B. Sridhar、S. Kiran Kumar、C. Suresh Reddy、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2014.05.083

  日期：2014.7

  A novel intramolecular Prins cyclization of (E)-5-(2-(hydroxymethyl)phenyl)pent-4-en-1-ol with aldehydes has been achieved using 10 mol % BF3 center dot Et2O to produce 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran derivatives in good to excellent yields with high selectivity. Similar type of coupling with salicylaldehydes provides the trans-fused hexahydropyrano[3,2-c]chromene derivatives in excellent yields. (C) 2014 Published by Elsevier Ltd.