1-chloro-9,10-dihydro-9,10-[1',2']benzeno-2,3-diazaanthracene | 1001639-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-chloro-9,10-dihydro-9,10-[1',2']benzeno-2,3-diazaanthracene
• 英文别名: 3-Chloro-4,5-diazapentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
• CAS: 1001639-80-0
• 化学式: C₁₈H₁₁ClN₂
• 分子量: 290.752
• InChiKey: RKCHSOHHWVVJRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-9,10-dihydro-9,10-[1',2']benzeno-2,3-diazaanthracene 、 2-三丁基甲锡烷基噻吩 在 四(三苯基膦)钯 cesium fluoride 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以78%的产率得到9,10-dihydro-1-(2-thienyl)-9,10-[1',2']benzeno-2,3-diazaanthracene
  参考文献：
  名称：

  Iptycene-Derived Pyridazines and Phthalazines

  摘要：

  The synthesis of new heterocyclic oligo(phenylene) analogues based on soluble, nonaggregating 1,2-diazines is reported. Improved palladium-catalyzed reductive coupling methods were developed to allow for the preparation of large quantities of iptycene-derived bipyridazines and biphthalazines, and the controlled synthesis of well-defined oligomers up to sexipyridazine. Crystallographic, spectroscopic, and computational evidence indicate that in these analogues, hindrance at the ortho position is relaxed relative to poly(phenylenes). The resulting building blocks are promising for incorporation in conjugated electronics materials, and as new iptycene-derived ligands for transition metals.

  DOI：

  10.1021/jo702000d
• 作为产物：
  描述：

  9,10-dihydro-9,10-[1',2']benzeno-2,3-diazaanthracen-4(3H)-one 在 三氯氧磷 作用下， 以59%的产率得到1-chloro-9,10-dihydro-9,10-[1',2']benzeno-2,3-diazaanthracene
  参考文献：
  名称：

  Iptycene-Derived Pyridazines and Phthalazines

  摘要：

  The synthesis of new heterocyclic oligo(phenylene) analogues based on soluble, nonaggregating 1,2-diazines is reported. Improved palladium-catalyzed reductive coupling methods were developed to allow for the preparation of large quantities of iptycene-derived bipyridazines and biphthalazines, and the controlled synthesis of well-defined oligomers up to sexipyridazine. Crystallographic, spectroscopic, and computational evidence indicate that in these analogues, hindrance at the ortho position is relaxed relative to poly(phenylenes). The resulting building blocks are promising for incorporation in conjugated electronics materials, and as new iptycene-derived ligands for transition metals.

  DOI：

  10.1021/jo702000d

文献信息

• Iptycene-Derived Pyridazines and Phthalazines
  作者：Jean Bouffard、Robert F. Eaton、Peter Müller、Timothy M. Swager

  DOI：10.1021/jo702000d

  日期：2007.12.1

  The synthesis of new heterocyclic oligo(phenylene) analogues based on soluble, nonaggregating 1,2-diazines is reported. Improved palladium-catalyzed reductive coupling methods were developed to allow for the preparation of large quantities of iptycene-derived bipyridazines and biphthalazines, and the controlled synthesis of well-defined oligomers up to sexipyridazine. Crystallographic, spectroscopic, and computational evidence indicate that in these analogues, hindrance at the ortho position is relaxed relative to poly(phenylenes). The resulting building blocks are promising for incorporation in conjugated electronics materials, and as new iptycene-derived ligands for transition metals.