9-(naphthalen-1-yl)acridine | 474452-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(naphthalen-1-yl)acridine
• 英文别名: 9-(1-naphthyl)acridine；9-[1]naphthyl-acridine；9-[1]Naphthyl-acridin；9-Naphthalen-1-ylacridine
• CAS: 474452-91-0
• 化学式: C₂₃H₁₅N
• 分子量: 305.379
• InChiKey: LFOCEKKAMIHHEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(naphthalen-1-yl)acridine 、 三氟甲烷磺酸甲酯 生成
  参考文献：
  名称：

  萘-1,8-二基双（10-甲基ac）和相应的六苯乙烷衍生物中的短非键和长C–C键：表现出动态氧化还原特性的新电致变色对

  摘要：

  无色双螺ac基六苯基乙烷中极长的C–C键[1.696（3）Å]在电化学转化为橙色萘-1,8-二基双（时很容易裂解，其中两个阳离子单元被迫以面对面的方式重叠，显示出有史以来最短的C +  ⋯C +原子间接触，为2.927（7）Å。

  DOI：

  10.1016/j.tetlet.2004.09.071
• 作为产物：
  描述：

  吖啶酮 在 三溴化磷 、 C₅₄H₅₈BrN₃OPd 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 36.0h， 生成 9-(naphthalen-1-yl)acridine
  参考文献：
  名称：

  Acenaphthoimidazolylidene‐Ligated Palladacycle Enabled Suzuki‐Miyaura Cross‐Coupling Employing Equimolar Organoboron for Tri‐Ortho‐Substituted Bi(hetero)aryls and Teraryls

  摘要：

  AbstractThe Pd‐catalyzed Suzuki‐Miyaura cross‐couplings (SMRs) are utilized as the most practical method to construct C−C bond, especial for biaryls. However, a major disadvantage of current protocols is the requirement of excess organoboron coupling partner (1.5–3.0 equiv.). Herein, a novel palladacyclic 1,3‐bis(2,6‐diisopropylphenyl)acenaphthoimidazol‐2‐ylidene (AnIPr) precatalyst possessing a chiral oxazoline was designed, which enabled a general protocol towards bulky tri‐ortho‐substituted biaryls, ternaphthalenes and diarylanthracenes via the Pd‐catalyzed SMR employing equimolar organoborons and aryl bromides. A remarkable scope of substrates with various functional groups and heterocycles were well compatible with an adaptability to synthesize useful ligands.

  DOI：

  10.1002/chem.202300719

文献信息

• A magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle: an efficient and recyclable solid molecular catalyst for Suzuki–Miyaura cross-coupling of 9-chloroacridine
  作者：Qinyue Deng、Yajing Shen、Haibo Zhu、Tao Tu

  DOI：10.1039/c7cc06958h

  日期：——

  directly anchoring the structural defined acenaphthoimidazolylidene palladacycle with a long tail on magnetic nanoparticles (MNPs), and functioned as a solid molecular catalyst and exhibited extremely high catalytic activity towards the challenging Suzuki–Miyaura cross-coupling reactions between less-studied heterocyclic 9-chloroacridine and diverse boronic acids. Remarkably, the catalyst could be used 5

  坚固的磁性纳米粒子支撑的N-杂环卡宾-Palladacycle已通过将结构明确的啶咪唑亚甲基Palladacycle与长尾巴直接锚定在磁性纳米颗粒（MNP）上而容易地合成，并且起着固体分子催化剂的作用，并且对碳纳米管表现出极高的催化活性。研究较少的杂环9-氯ac啶与各种硼酸之间的具有挑战性的Suzuki-Miyaura交叉偶联反应。值得注意的是，该催化剂可以使用5次而不会明显失去活性，这突出了我们固定化催化剂的策略的效率。
• [EN] SYNTHESIS OF PHOSPHINE LIGANDS BEARING TUNABLE LINKAGE: METHODS OF THEIR USE IN CATALYSIS<br/>[FR] SYNTHÈSE DE LIGANDS DE PHOSPHINE PORTANT UNE LIAISON RÉGLABLE : PROCÉDÉS POUR LEUR UTILISATION DANS UNE CATALYSE
  申请人：THE HONG KONG POLYTECHNIC UNIV SHENZHEN RESEARCH INSTITUTE

  公开号：WO2017193288A1

  公开（公告）日：2017-11-16

  A series of novel linked indolyl phosphine ligands for transition metals, the synthesis thereof and their use in catalytic coupling reactions are provided. The ligands provide improvements of trasition-metal-catalyzed reactions, including the range of substrates scope, reaction conditions and efficieny.

  提供一系列新型的连接吲哚基膦配体用于过渡金属，其合成以及它们在催化偶联反应中的应用。这些配体提供了对过渡金属催化反应的改进，包括底物范围、反应条件和效率。
• Short nonbond and long C–C bond in naphthalene-1,8-diylbis(10-methylacridinium) and the corresponding hexaphenylethane derivative: a new electrochromic pair exhibiting dynamic redox properties
  作者：Hidetoshi Kawai、Takashi Takeda、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1016/j.tetlet.2004.09.071

  日期：2004.11

  The extremely long C–C bond [1.696(3) Å] in the colorless dispiroacenaphthene-type hexaphenylethane is cleaved readily upon electrochemical transformation into the orange colored naphthalene-1,8-diylbis(acridinium), in which the two cationic units are forced to overlap in a face-to-face manner exhibiting the shortest C+ ⋯ C+ interatomic contact of 2.927(7) Å among the values ever reported.

  无色双螺ac基六苯基乙烷中极长的C–C键[1.696（3）Å]在电化学转化为橙色萘-1,8-二基双（时很容易裂解，其中两个阳离子单元被迫以面对面的方式重叠，显示出有史以来最短的C +  ⋯C +原子间接触，为2.927（7）Å。
• Unexpected Cyclization of Tritylamines Promoted by Copper Salt through CH and CN Bond Cleavages to Produce Acridine Derivatives
  作者：Ryosuke Morioka、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1002/chem.201404656

  日期：2014.9.26

  tritylamines undergo an unprecedented copper‐mediated cyclization involving the cleavages of two CH bonds and one CN bond to give 9‐arylacridine derivatives. This kind of acridines is of interest due to their biological properties and their unique optical and electro‐ and photochemical properties. Some of obtained acridine derivatives exhibit intense fluorescence in the solid state.

  在本文中，我们表明，tritylamines经历涉及的两个C劈裂前所未有的铜介导的环化 H键和一种C  N键，得到9- arylacridine衍生物。这种their啶因其生物学特性以及独特的光学，电化学和光化学特性而备受关注。某些获得的a啶衍生物在固态下表现出强烈的荧光。
• 236. The chemistry of carcinogenic nitrogen compounds. Part IV. New substituted angular benzacridines and dibenzacridines
  作者：Ng. Ph. Buu-Hoï

  DOI：10.1039/jr9500001146

  日期：——