1,6-anhydro-3,4-O-fluoren-9-ylidene-β-D-galactopyranose | 196806-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1,6-anhydro-3,4-O-fluoren-9-ylidene-β-D-galactopyranose
• CAS: 196806-89-0
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: FNXMYMSOBNAZIX-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  1,6-anhydro-3,4-O-fluoren-9-ylidene-β-D-galactopyranose 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1,6-anhydro-2-O-benzyl-3-O-fluoren-9-yl-β-D-galactopyranose
  参考文献：
  名称：

  Synthesis and Hydrogenolysis of Dioxolane-Type Diphenyl-Methylene and Fluoren-9-Ylidene Carbohydrate Acetals Containing a Neighbouring Substituted Hydroxyl Function

  摘要：

  Series of dioxolane-type diphenylmethylene and fluoren-9-ylidene acetals of hexoses containing adjacent O-alkyl, deoxy or hydroxy functions were prepared and hydrogenolysed with the LiAlH4-AlCl3 reagent. The observed direction of ring-cleavage was discussed in terms of different influences, such as complex formation and orientation of the hydride reagent, the configurational arrangements of the free OH group to one of the oxygen atoms of the dioxolane ring, as well as the conformational relationship of the rings present in the 1,6-anhydro derivatives.

  DOI：

  10.1080/07328309708005742
• 作为产物：
  描述：

  9,9-二氯芴 、 1,6-内醚-D-半乳糖 以 吡啶 为溶剂， 反应 96.0h， 以42%的产率得到1,6-anhydro-3,4-O-fluoren-9-ylidene-β-D-galactopyranose
  参考文献：
  名称：

  Synthesis and Hydrogenolysis of Dioxolane-Type Diphenyl-Methylene and Fluoren-9-Ylidene Carbohydrate Acetals Containing a Neighbouring Substituted Hydroxyl Function

  摘要：

  Series of dioxolane-type diphenylmethylene and fluoren-9-ylidene acetals of hexoses containing adjacent O-alkyl, deoxy or hydroxy functions were prepared and hydrogenolysed with the LiAlH4-AlCl3 reagent. The observed direction of ring-cleavage was discussed in terms of different influences, such as complex formation and orientation of the hydride reagent, the configurational arrangements of the free OH group to one of the oxygen atoms of the dioxolane ring, as well as the conformational relationship of the rings present in the 1,6-anhydro derivatives.

  DOI：

  10.1080/07328309708005742