3-((4aR,8R,8aS)-8-methoxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl)propan-1-ol | 1375015-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 3-((4aR,8R,8aS)-8-methoxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl)propan-1-ol
• CAS: 1375015-15-8
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: IAVAALPVYMBFFQ-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-((4aR,8R,8aS)-8-methoxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl)propan-1-ol 在 (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 作用下， 以 正戊烷 为溶剂， 反应 14.0h， 以42%的产率得到(2R,4a'R,8'R,8a'S)-8'-methoxy-2',2'-dimethylhexahydro-3H,4'H-spiro[furan-2,6'-pyrano[3,2-d][1,3]dioxin]
  参考文献：
  名称：

  Chiral Phosphoric Acid-Catalyzed Enantioselective and Diastereoselective Spiroketalizations

  摘要：

  Catalytic enantioselective and diastereoselective spiroketalizations with BINOL-derived chiral phosphoric acids are reported. The chiral catalyst can override the inherent preference for the formation of thermodynamic spiroketals, and highly selective formation of nonthermodynamic spiroketals could be achieved under the reaction conditions.

  DOI：

  10.1021/ja302704m
• 作为产物：
  描述：

  1,5-anhydro-1-iodo-4,6-(O-isopropylidene)-3-(O-triisopropylsilyl)-2-deoxy-D-arabino-hex-1-enitol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 3-((4aR,8R,8aS)-8-methoxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl)propan-1-ol
  参考文献：
  名称：

  Chiral Phosphoric Acid-Catalyzed Enantioselective and Diastereoselective Spiroketalizations

  摘要：

  Catalytic enantioselective and diastereoselective spiroketalizations with BINOL-derived chiral phosphoric acids are reported. The chiral catalyst can override the inherent preference for the formation of thermodynamic spiroketals, and highly selective formation of nonthermodynamic spiroketals could be achieved under the reaction conditions.

  DOI：

  10.1021/ja302704m