1,3,7,8-Tetramethyl-5H-pyrido(4,3-b)indole | 180520-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,3,7,8-Tetramethyl-5H-pyrido(4,3-b)indole
• 英文别名: 1,3,7,8-tetramethyl-5H-pyrido[4,3-b]indole
• CAS: 180520-52-9
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: QIGKOOKPOYQMDH-UHFFFAOYSA-N

物化性质

• 沸点：
  418.0±40.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3,7,8-Tetramethyl-5H-pyrido(4,3-b)indole 在 二正丁胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 2,3-diethyl-6,10,11-trimethyl-8H-pyridazino<1',6':1,2>pyrido<4,3-b>indol-5-inium mesitylenesulfonate
  参考文献：
  名称：

  Novel DNA Intercalators Based on the Pyridazino[1‘,6‘:1,2]pyrido[4,3-b]indol-5-inium System

  摘要：

  A new class of DNA intercalators based on the 8H-pyridazino[1',6':1,2]pyrido[4,3-b]indol-5-inium system in which the cationic nature of the chromophore is provided by a brigdehead quaternary nitrogen has been obtained. These cations along with 10H-indolo[3,2-c]pyridazino[1,6-a]quinolin-5-inium, 13H-dibenz[f,h]indolo[3',2':3,4]pyrido[1,2-b]cinnolin-10-inium, and 5H-acenaphtho[1',2: 3',4']pyridazino[1',6':1,2]pyrido[4,3-b]indol-8-inium were synthesized by the Westphal reaction of carbolinium derivatives with various 1,2-dicarbonyl compounds. When these tetra-, penta-, and heptacyclic heteroaromatic nuclei were evaluated as DNA intercalators using UV-vis spectroscopy, viscometric determinations, and unwinding angle determinations, we found that only the 8H-pyridazino[1',6':1,2]pyrido[4,3-b]indol-5-inium cations behaved as DNA intercalators. Molecular modeling studies allowed the preferred orientation of the intercalating chromophore within a CpG intercalation site to be explored and will provide help in the rational design of novel bis-intercalators based on these chromophores.

  DOI：

  10.1021/jo982216d
• 作为产物：
  描述：

  4-氯-2,6-二甲基吡啶 在 焦磷酸 作用下， 反应 0.5h， 生成 1,3,7,8-Tetramethyl-5H-pyrido(4,3-b)indole
  参考文献：
  名称：

  Synthesis and DNA Binding Properties of γ-Carbolinium Derivatives and Benzologues

  摘要：

  The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe-Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds were transformed into the corresponding cationic derivatives by N-alkylation, and the DNA-binding properties of the resulting cationic systems were examined using UV-vis spectroscopy, viscometric determinations, and molecular modeling techniques. The tetracyclic cations were transformed into his-salts by means of a diethyl bispiperidine rigid chain and a more flexible polyamide linker, but the low solubility of these bis-salts made the study of their bisintercalating properties difficult.

  DOI：

  10.1021/jo960266h

文献信息

• MATERIALS FOR ELECTRONIC DEVICES
  申请人：MERCK PATENT GMBH

  公开号：US20160072076A1

  公开（公告）日：2016-03-10

  The present application relates to a compound of a formula (I) which comprises a benzene group that is substituted with a group selected from carbazole derivatives and bridged amines and with an electron attracting group, wherein the two groups are located in the ortho-position in relation to one another. The present application further relates to the use of the compound of the formula (I) in an electronic device, and to a method of producing the compound of the formula (I).

  本申请涉及一种化合物，其化学式为(I)，包括一个苯基，该苯基被取代为由咔唑衍生物和桥式胺组成的基团和一个吸电子基团，其中这两个基团位于相对的邻位。本申请还涉及在电子器件中使用化合物(I)的方法，以及制备化合物(I)的方法。
• Materials for electronic devices
  申请人：Merck Patent GmbH

  公开号：US10193079B2

  公开（公告）日：2019-01-29

  The present application relates to a compound of a formula (I) which comprises a benzene group that is substituted with a group selected from carbazole derivatives and bridged amines and with an electron attracting group, wherein the two groups are located in the ortho-position in relation to one another. The present application further relates to the use of the compound of the formula (I) in an electronic device, and to a method of producing the compound of the formula (I).

  本申请涉及一种式(I)化合物，它包括一个苯基，该苯基被一个选自咔唑衍生物和桥胺的基团以及一个引电子基团取代，其中这两个基团彼此位于正交位置。本申请还涉及式（I）化合物在电子设备中的用途，以及式（I）化合物的生产方法。
• MATERIALIEN FÜR ELEKTRONISCHE VORRICHTUNGEN
  申请人：Merck Patent GmbH

  公开号：EP2976329B1

  公开（公告）日：2018-06-27
• [DE] MATERIALIEN FÜR ELEKTRONISCHE VORRICHTUNGEN<br/>[EN] MATERIALS FOR ELECTRONIC DEVICES<br/>[FR] MATÉRIAUX POUR DISPOSITIFS ÉLECTRONIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2014146752A1

  公开（公告）日：2014-09-25

  Die vorliegende Anmeldung betrifft eine Verbindung einer Formel (I), welche eine Benzolgruppe aufweist, die mit einer Gruppe gewählt aus Carbazolderivaten und verbrückten Aminen und mit einer elektronenziehenden Gruppe substituiert ist, wobei die beiden Gruppen in ortho-Position zueinander stehen. Weiterhin betrifft die vorliegende Anmeldung die Verwendung der Verbindung der Formel (I) in einer elektronischen Vorrichtung, und Verfahren zur Herstellung der Verbindung der Formel (I).