(+/-)-(3aR,4R,7aS)-4-phenylhexahydro-2H-furo[3,2-c]pyran

• 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: (+/-)-(3aR,4R,7aS)-4-phenylhexahydro-2H-furo[3,2-c]pyran
• 英文别名: (3aR,4R,7aS)-4-phenyl-3,3a,4,6,7,7a-hexahydro-2H-furo[3,2-c]pyran
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: BABOBJMBCSEXOE-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (3E)-3-己烯-1,6-二醇 、 苯甲醛 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 14.0h， 以52%的产率得到(+/-)-(3aR,4R,7aS)-4-phenylhexahydro-2H-furo[3,2-c]pyran
  参考文献：
  名称：

  Intramolecular-Prins-cyclization: a novel synthesis of hexahydro-2H-furo[3,2-c]pyran derivatives

  摘要：

  p-Toluenesulfonic acid is found to catalyze the coupling of (Z)-hex-3-ene-1,6-diol with a series of aldehydes by means of intramolecular-Prins-cyclization to provide the corresponding hexahydro-2H-furo[3,2-c]pyran derivatives in good yields with complete cis-selectivity, whereas the coupling of (E)-hex-3-ene-1,6-diol with aliphatic aldehydes gave trans-fused bicyclic furopyrans. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.023

文献信息

• Intramolecular-Prins-cyclization: a novel synthesis of hexahydro-2H-furo[3,2-c]pyran derivatives
  作者：J.S. Yadav、P. Pawan Chakravarthy、Prashant Borkar、B.V. Subba Reddy、A.V.S. Sarma

  DOI：10.1016/j.tetlet.2009.08.023

  日期：2009.11

  p-Toluenesulfonic acid is found to catalyze the coupling of (Z)-hex-3-ene-1,6-diol with a series of aldehydes by means of intramolecular-Prins-cyclization to provide the corresponding hexahydro-2H-furo[3,2-c]pyran derivatives in good yields with complete cis-selectivity, whereas the coupling of (E)-hex-3-ene-1,6-diol with aliphatic aldehydes gave trans-fused bicyclic furopyrans. (C) 2009 Elsevier Ltd. All rights reserved.