3,6-bis(prop-2-yn-1-yloxy)-9H-xanthen-9-one | 1261351-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,6-bis(prop-2-yn-1-yloxy)-9H-xanthen-9-one
• 英文别名: 3,6-Bis(prop-2-ynoxy)xanthen-9-one；3,6-bis(prop-2-ynoxy)xanthen-9-one
• CAS: 1261351-50-1
• 化学式: C₁₉H₁₂O₄
• 分子量: 304.302
• InChiKey: BFILSOMYBDOXAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,11,22,30,45,52-Hexazanonacyclo[30.6.6.613,20.15,9.124,28.014,19.033,38.039,44.046,51]dopentaconta-1(38),5(52),6,8,13(51),14,16,18,20(46),24,26,28(45),32,34,36,39,41,43,47,49-icosaene-4,10,23,29-tetrone 、 3,6-bis(prop-2-yn-1-yloxy)-9H-xanthen-9-one 以 氯仿 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Macrocycle Breathing in [2]Rotaxanes with Tetralactam Macrocycles

  摘要：

  The structural dynamics of two pairs of [2]rotaxanes were compared using variable-temperature NMR. Each rotaxane had a surrounding tetralactam macrocycle with either 2,6-pyridine dicarboxamide or isophthalamide bridging units. Differences were observed in two types of rotational processes: spinning of the phenylene wall units in the surrounding macrocycle of squaraine rotaxanes and macrocycle pirouetting in xanthone rotaxanes. The rotaxanes with macrocycles containing 2,6-pyridine dicarboxamide bridges exhibited higher rotational barriers due to a cavity contraction effect, which disfavored macrocycle breathing.

  DOI：

  10.1021/jo1020739
• 作为产物：
  描述：

  3,6-二羟基-9H-氧杂蒽-9-酮 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以79%的产率得到3,6-bis(prop-2-yn-1-yloxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Macrocycle Breathing in [2]Rotaxanes with Tetralactam Macrocycles

  摘要：

  The structural dynamics of two pairs of [2]rotaxanes were compared using variable-temperature NMR. Each rotaxane had a surrounding tetralactam macrocycle with either 2,6-pyridine dicarboxamide or isophthalamide bridging units. Differences were observed in two types of rotational processes: spinning of the phenylene wall units in the surrounding macrocycle of squaraine rotaxanes and macrocycle pirouetting in xanthone rotaxanes. The rotaxanes with macrocycles containing 2,6-pyridine dicarboxamide bridges exhibited higher rotational barriers due to a cavity contraction effect, which disfavored macrocycle breathing.

  DOI：

  10.1021/jo1020739

文献信息

• Macrocycle Breathing in [2]Rotaxanes with Tetralactam Macrocycles
  作者：Ivan Murgu、Jeffrey M. Baumes、Jens Eberhard、Jeremiah J. Gassensmith、Easwaran Arunkumar、Bradley D. Smith

  DOI：10.1021/jo1020739

  日期：2011.1.21

  The structural dynamics of two pairs of [2]rotaxanes were compared using variable-temperature NMR. Each rotaxane had a surrounding tetralactam macrocycle with either 2,6-pyridine dicarboxamide or isophthalamide bridging units. Differences were observed in two types of rotational processes: spinning of the phenylene wall units in the surrounding macrocycle of squaraine rotaxanes and macrocycle pirouetting in xanthone rotaxanes. The rotaxanes with macrocycles containing 2,6-pyridine dicarboxamide bridges exhibited higher rotational barriers due to a cavity contraction effect, which disfavored macrocycle breathing.