(3-Iodo-azulen-1-yl)-phenyl-methanone | 916584-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-Iodo-azulen-1-yl)-phenyl-methanone
• 英文别名: (3-Iodoazulen-1-yl)(phenyl)methanone；(3-iodoazulen-1-yl)-phenylmethanone
• CAS: 916584-39-9
• 化学式: C₁₇H₁₁IO
• 分子量: 358.178
• InChiKey: ZMIAKCOIHOZAHX-UHFFFAOYSA-N

物化性质

• 沸点：
  472.0±28.0 °C(Predicted)
• 密度：
  1.600±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3-Iodo-azulen-1-yl)-phenyl-methanone 、 2-萘硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以92%的产率得到1-benzoyl-3-(2-naphthyl)azulene
  参考文献：
  名称：

  Synthesis of N,N,N′,N′-tetrasubstituted 1,3-bis(4-aminophenyl)azulenes and their application to a hole-injecting material in organic electroluminescent devices

  摘要：

  After a preliminary search of the reaction conditions for the Suzuki-Miyaura cross-coupling of haloazulenes with arylboronic acids, the title compounds were synthesized either by the direct coupling reaction between 1,3-dihaloazulene and the corresponding N,N-disubstituted 4-aminophenylboronic acids or by a two-step sequence involving the cross-coupling with 4-bromophenylboronic acid and subsequent Pd-catalyzed amination. Application of the title diamines to a hole-injecting material in organic electroluminescent devices was carried out to provide their prominent characteristics as a novel durable, non-cyanine and non-polyamine substance without color fade. The diamine derivatives, extended by an ethynyl unit between the azulenyl core and the 4-aminophenyl moiety, were also synthesized and found, unfortunately, unsuitable for vacuum deposition in preparing a multilayer composite. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.025
• 作为产物：
  描述：

  1-benzoylazulene 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以94%的产率得到(3-Iodo-azulen-1-yl)-phenyl-methanone
  参考文献：
  名称：

  Synthesis of N,N,N′,N′-tetrasubstituted 1,3-bis(4-aminophenyl)azulenes and their application to a hole-injecting material in organic electroluminescent devices

  摘要：

  After a preliminary search of the reaction conditions for the Suzuki-Miyaura cross-coupling of haloazulenes with arylboronic acids, the title compounds were synthesized either by the direct coupling reaction between 1,3-dihaloazulene and the corresponding N,N-disubstituted 4-aminophenylboronic acids or by a two-step sequence involving the cross-coupling with 4-bromophenylboronic acid and subsequent Pd-catalyzed amination. Application of the title diamines to a hole-injecting material in organic electroluminescent devices was carried out to provide their prominent characteristics as a novel durable, non-cyanine and non-polyamine substance without color fade. The diamine derivatives, extended by an ethynyl unit between the azulenyl core and the 4-aminophenyl moiety, were also synthesized and found, unfortunately, unsuitable for vacuum deposition in preparing a multilayer composite. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.025

文献信息

• Synthesis of N,N,N′,N′-tetrasubstituted 1,3-bis(4-aminophenyl)azulenes and their application to a hole-injecting material in organic electroluminescent devices
  作者：Nguyen Chung Thanh、Masamichi Ikai、Takanori Kajioka、Hisayoshi Fujikawa、Yasunori Taga、Yanmei Zhang、Satoshi Ogawa、Hiroko Shimada、Yosuke Miyahara、Shigeyasu Kuroda、Mitsunori Oda

  DOI：10.1016/j.tet.2006.09.025

  日期：2006.11

  After a preliminary search of the reaction conditions for the Suzuki-Miyaura cross-coupling of haloazulenes with arylboronic acids, the title compounds were synthesized either by the direct coupling reaction between 1,3-dihaloazulene and the corresponding N,N-disubstituted 4-aminophenylboronic acids or by a two-step sequence involving the cross-coupling with 4-bromophenylboronic acid and subsequent Pd-catalyzed amination. Application of the title diamines to a hole-injecting material in organic electroluminescent devices was carried out to provide their prominent characteristics as a novel durable, non-cyanine and non-polyamine substance without color fade. The diamine derivatives, extended by an ethynyl unit between the azulenyl core and the 4-aminophenyl moiety, were also synthesized and found, unfortunately, unsuitable for vacuum deposition in preparing a multilayer composite. (c) 2006 Elsevier Ltd. All rights reserved.