(12-Carbazol-9-yl-dodecyl)-[4-(4-nitro-phenylazo)-phenyl]-amine | 286474-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: (12-Carbazol-9-yl-dodecyl)-[4-(4-nitro-phenylazo)-phenyl]-amine
• 英文别名: N-(12-carbazol-9-yldodecyl)-4-[(4-nitrophenyl)diazenyl]aniline
• CAS: 286474-51-9
• 化学式: C₃₆H₄₁N₅O₂
• 分子量: 575.754
• InChiKey: VFWBUOIATVFKHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-溴戊烷 、 (12-Carbazol-9-yl-dodecyl)-[4-(4-nitro-phenylazo)-phenyl]-amine 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 苯 为溶剂， 以89%的产率得到N-(12-carbazol-9-yldodecyl)-4-[(4-nitrophenyl)diazenyl]-N-pentylaniline
  参考文献：
  名称：

  Phase Transfer Catalysis for Tandem Alkylation of Azo Dyes for the Synthesis of Novel Multifunctional Molecules

  摘要：

  Potentially photorefractive molecules, which possess both a charge transfer component and a nonlinear optical chromophore, were prepared by the direct N-monoalkylation of Disperse Orange 3 (1) with a carbazole alkyl bromide (2) utilizing phase transfer catalysis. Further N-alkylation of the remaining active N-H with alkyl halides with various chain lengths allowed the thermal properties of the Disperse Orange 3 derivatives to be fine-tuned. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00536-6
• 作为产物：
  描述：

  1,12-二溴十二烷 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 生成 (12-Carbazol-9-yl-dodecyl)-[4-(4-nitro-phenylazo)-phenyl]-amine
  参考文献：
  名称：

  Phase Transfer Catalysis for Tandem Alkylation of Azo Dyes for the Synthesis of Novel Multifunctional Molecules

  摘要：

  Potentially photorefractive molecules, which possess both a charge transfer component and a nonlinear optical chromophore, were prepared by the direct N-monoalkylation of Disperse Orange 3 (1) with a carbazole alkyl bromide (2) utilizing phase transfer catalysis. Further N-alkylation of the remaining active N-H with alkyl halides with various chain lengths allowed the thermal properties of the Disperse Orange 3 derivatives to be fine-tuned. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00536-6

文献信息

• Combined phase transfer catalysis and ultrasound to enhance tandem alkylation of azo dyes
  作者：Xiang Li、Jie Wang、Richard Mason、Xiu R Bu、Joycelyn Harrison

  DOI：10.1016/s0040-4020(02)00331-9

  日期：2002.5

  Ultrasound has been found to enhance N-substitution against elimination in the reaction of carbazole-containing bromides 3 with a Disperse Orange 3 derivative 2 under PTC condition. Upon using combined PTC and ultrasound conditions, a series of bifunctional molecules 1 have been prepared to possess charge-transporting agents and nonlinear optical chromophores in 2:1 ratio.

  已经发现，在PTC条件下，在含咔唑的溴化物3与分散橙3衍生物2的反应中，超声波增强了N-取代抵抗消除。在结合使用PTC和超声条件的情况下，已准备了一系列双功能分子1，使其具有电荷传输剂和非线性光学发色团，其比率为2：1。
• Phase Transfer Catalysis for Tandem Alkylation of Azo Dyes for the Synthesis of Novel Multifunctional Molecules
  作者：Xiang Li、Eric A Mintz、Xiu R Bu、Oliver Zehnder、Christian Bosshard、Peter Günter

  DOI：10.1016/s0040-4020(00)00536-6

  日期：2000.8

  Potentially photorefractive molecules, which possess both a charge transfer component and a nonlinear optical chromophore, were prepared by the direct N-monoalkylation of Disperse Orange 3 (1) with a carbazole alkyl bromide (2) utilizing phase transfer catalysis. Further N-alkylation of the remaining active N-H with alkyl halides with various chain lengths allowed the thermal properties of the Disperse Orange 3 derivatives to be fine-tuned. (C) 2000 Elsevier Science Ltd. All rights reserved.