1,1'-((2,5-dibromo-1,4-phenylene)bis(ethyne-2,1-diyl))bis(cyclohexan-1-ol) | 1191422-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1'-((2,5-dibromo-1,4-phenylene)bis(ethyne-2,1-diyl))bis(cyclohexan-1-ol)
• CAS: 1191422-03-3
• 化学式: C₂₂H₂₄Br₂O₂
• 分子量: 480.239
• InChiKey: CTQFYUXDTCKYLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  26.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1'-((2,5-dibromo-1,4-phenylene)bis(ethyne-2,1-diyl))bis(cyclohexan-1-ol) 、 3,4-二甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 48.0h， 以99%的产率得到
  参考文献：
  名称：

  A Versatile Preparation of Geländer-Type p-Terphenyls from a Readily Available Diacetylenic Precursor

  摘要：

  A series of doubly bridged p-terphenyls (4) have been synthesized utilizing a facile three-step synthesis starting from the readily available diacetylenic precursor (1) in excellent overall yields, and their structures were confirmed by H-1/C-13 NMR spectroscopy as well as by X-ray crystallography. The racemization barrier between the meso and chiral atropisomers; of one of the derivatives of 4 was found to be similar to 12 kcal/mol by variable-temperature NMR spectroscopy. The versatility of the protocol developed herein was further demonstrated by the preparation of a quadruply bridged penta-p-phenylene derivative.

  DOI：

  10.1021/ol901938f
• 作为产物：
  描述：

  1,4-二溴-2,5-二碘苯 、 炔环己醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 苯 为溶剂， 以87%的产率得到1,1'-((2,5-dibromo-1,4-phenylene)bis(ethyne-2,1-diyl))bis(cyclohexan-1-ol)
  参考文献：
  名称：

  A Versatile Preparation of Geländer-Type p-Terphenyls from a Readily Available Diacetylenic Precursor

  摘要：

  A series of doubly bridged p-terphenyls (4) have been synthesized utilizing a facile three-step synthesis starting from the readily available diacetylenic precursor (1) in excellent overall yields, and their structures were confirmed by H-1/C-13 NMR spectroscopy as well as by X-ray crystallography. The racemization barrier between the meso and chiral atropisomers; of one of the derivatives of 4 was found to be similar to 12 kcal/mol by variable-temperature NMR spectroscopy. The versatility of the protocol developed herein was further demonstrated by the preparation of a quadruply bridged penta-p-phenylene derivative.

  DOI：

  10.1021/ol901938f