(3aR,4aR,4bS,5R,8aS,9aS,9bR)-5-(m-tolyl)octahydro-3aH-spiro([1,3]dioxolo[4'',5'':4',5']furo[2',3':4,5]furo[3,2-c]pyran-2,1'-cyclohexane) | 1449414-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3aR,4aR,4bS,5R,8aS,9aS,9bR)-5-(m-tolyl)octahydro-3aH-spiro([1,3]dioxolo[4'',5'':4',5']furo[2',3':4,5]furo[3,2-c]pyran-2,1'-cyclohexane)
• 英文别名: (1R,2S,3R,7S,9S,10R,14R)-3-(3-methylphenyl)spiro[4,8,11,13,15-pentaoxatetracyclo[7.6.0.02,7.010,14]pentadecane-12,1'-cyclohexane]
• CAS: 1449414-52-1
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: ULPXGSKMOIDTKD-JPSLMIEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5'-[(Z)-4-hydroxybut-1-en-1-yl]tetrahydrospiro(cyclohexane-1,2'-furo[2,3-d][1,3]dioxol)-6'-ol 、 3-甲基苯甲醛 在 indium(III) triflate 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.1h， 以68%的产率得到(3aR,4aR,4bS,5R,8aS,9aS,9bR)-5-(m-tolyl)octahydro-3aH-spiro([1,3]dioxolo[4'',5'':4',5']furo[2',3':4,5]furo[3,2-c]pyran-2,1'-cyclohexane)
  参考文献：
  名称：

  A Novel Prins Bicyclization Strategy for the Synthesis of Sugar Annulated Furopyran Scaffolds

  摘要：

  A tandem Prins bicyclization of sugar-derived homoallylic diols with aldehydes has been accomplished using 10 mol% of In(OTf)(3) and 20 mol% of TsOH at ambient temperature to produce a novel series of sugar-annulated furopyran derivatives in good yields with high selectivity. This is the first report on Prins bicyclization of homoallylic diols derived from sugars. The cooperative catalysis between In(OTf)(3) and TsOH provides high conversions and enhanced reaction rates.

  DOI：

  10.1055/s-0033-1338708