2-phenyl-2H-phenanthro[9,10-d][1,2,3]triazole | 973-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-phenyl-2H-phenanthro[9,10-d][1,2,3]triazole
• 英文别名: 2-Phenyl-2H-phenanthro(9,10-d)triazole；2-phenylphenanthro[9,10-d]triazole
• CAS: 973-14-8
• 化学式: C₂₀H₁₃N₃
• 分子量: 295.343
• InChiKey: YEYUESDYKNXPEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 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：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-2H-phenanthro[9,10-d][1,2,3]triazole 、 硫酸二甲酯 在 sodium perchlorate 作用下， 生成 1-Methyl-2-phenyl-2H-phenanthro[9,10-d][1,2,3]triazol-1-ium; perchlorate
  参考文献：
  名称：

  New phenanthrene systems: spiro-fused tricyclic phenanthro-1,2,4-triazolo-[4,3-d]-1,2,4-triazines and -[3,4-d]-1,2,5-oxadiazines: ring expansions of N-methylphenanthroazoliums

  摘要：

  介绍了取代菲罗[9,10-e]-1,2,4-三嗪和菲罗[9,10-c]-1,2,5-恶二嗪的新路线。 这些化合物与 C-苯基-N-对硝基苯腈亚胺[IUPAC 名称：2-苄叉-1-(对硝基苯基)肼-2-鎓-1-ide]发生环加成反应，生成了新的取代的螺三环菲并-1,2,4-三唑并[4,3-d][1,2,4]三嗪和菲并-1,2,4-三唑并[3,4-d][1,2,5]恶二嗪。报告了 7,10-二苯基-5-（4′-硝基苯基）-9,10-二氢-5H-菲罗[9,10-e][1,2,4]三唑并[4,3-d][1,2,4]三嗪 5a 的 X 射线晶体结构。

  DOI：

  10.1039/a605770e
• 作为产物：
  描述：

  9,10-Bis(phenylazo)phenanthrene 在 三氯化磷 作用下， 反应 1.0h， 以93%的产率得到2-phenyl-2H-phenanthro[9,10-d][1,2,3]triazole
  参考文献：
  名称：

  Tricyclic phenanthrene systems: substituted phenanthro[9,10-e]-1,2,3-triazines and fused phenanthro-azolo-1,2,3-triazoles from cycloaddition—rearrangement sequences of 9,10-bisarylazophenanthrenes with 2π-dipolarophiles. Azolium 1,3-dipoles

  摘要：

  A range of new fused ring systems based on phenanthrene were obtained from cycloaddition-rearrangement reactions of 9, 10-bisarylazophenanthrenes with alkyne and alkene dipolarophilles. These new rings include substituted phenanthro[9,10-e]-1,2,3-triazines, the tricyclic systems, substituted 3a,6a-(biphen-2,2'-yl)hexahydropyrrolo[2, 3-d]-1,2,3-triazoles and substituted 3a,6a-(biphen-2,2'-yl)hexahydroimidazo[4,5-d]-1,2,3-triazoles. X-Ray crystal structures are reported on 2-(p-bromophenyl)-4 -methoxycarbonyl-4-(p-bromophenyliminomethoxalyl)-3,4-dihydrophenanthro[9,10-e]-1,2,3-triazin-2-ium-3-ide 6b, and 2,4-diphenyl-3a,6a-(biphen-2,2'-yl)-5,6-hexahydropyrrolo[2,3-d]-1,2, 3-triazol-2-ium-1-ide 11a.

  DOI：

  10.1039/p19960001623

文献信息

• Competitive reactivity of the aryl isothiocyanate dipolarophile at NC versus CS with nucleophilic 1,3-dipoles: a combined experimental and theoretical study. The reactions of substituted 1,2,3-triazolium-1-aminide 1,3-dipoles with aryl isothiocyanates: new tricyclic thiazolo[4,5-d][1,2,3]triazoles
  作者：Richard N. Butler、Denise C. Grogan、Peter D. McDonald、Luke A. Burke

  DOI：10.1039/a705233b

  日期：——

  Substituted 1,2,3-triazolium-1-aminide 1,3-dipoles react with aryl isothiocyanates at both the NC and CS sites to give mixtures of substituted imidazolo[4,5-d][1,2,3]triazoles and new thiazolo[4,5-d][1,2,3]triazoles including tricyclic derivatives with the C-3a and C-6a bridgeheads linked via (CH2)4 and phenanthro groups. The product distribution is controlled by the para-substituent of the aryl isothiocyanate. Theoretical calculations, 3-21G* and 6-31G*, suggest that linear triple bonded canonical forms of the aryl isothiocyanate system play a key role in the ambident reactivity of these systems.

  取代的 1,2,3-三唑鎓-1-氨基 1,3-二极体与芳基异硫氰酸酯在 NC 和 CS 位点发生反应，生成取代的咪唑并[4,5-d][1,2,3]三唑和新的噻唑并[4,5-d][1,2,3]三唑混合物，包括 C-3a 和 C-6a 桥头通过 (CH2)4 和菲基连接的三环衍生物。产品的分布受异硫氰酸芳基对位基团的控制。3-21G* 和 6-31G* 理论计算表明，芳基异硫氰酸酯体系的线性三键典型形式在这些体系的歧化反应性中起着关键作用。
• OLED WITH HYBRID EMISSIVE LAYER
  申请人：The University of Southern California

  公开号：US20190237694A1

  公开（公告）日：2019-08-01

  A hybrid emissive layer and OLED incorporating the same are provided. The hybrid emissive layer includes a first material having a triplet state energy level T1 H and a singlet state energy level S1 H , a second material having a triplet state energy level T1 F and a singlet state energy level S1 F ; and a third material having a triplet state energy level T1 P and a single state energy level S1 P , where T1 F ≥T1 H ; S1 F ≤S1 H ; and T1 P
• Tricyclic phenanthrene systems: substituted phenanthro[9,10-e]-1,2,3-triazines and fused phenanthro-azolo-1,2,3-triazoles from cycloaddition—rearrangement sequences of 9,10-bisarylazophenanthrenes with 2π-dipolarophiles. Azolium 1,3-dipoles
  作者：Richard N. Butler、Fiona A. Lysaght、Peter D. McDonald、Carmel S. Pyne、Patrick McArdle、Desmond Cunningham

  DOI：10.1039/p19960001623

  日期：——

  A range of new fused ring systems based on phenanthrene were obtained from cycloaddition-rearrangement reactions of 9, 10-bisarylazophenanthrenes with alkyne and alkene dipolarophilles. These new rings include substituted phenanthro[9,10-e]-1,2,3-triazines, the tricyclic systems, substituted 3a,6a-(biphen-2,2'-yl)hexahydropyrrolo[2, 3-d]-1,2,3-triazoles and substituted 3a,6a-(biphen-2,2'-yl)hexahydroimidazo[4,5-d]-1,2,3-triazoles. X-Ray crystal structures are reported on 2-(p-bromophenyl)-4 -methoxycarbonyl-4-(p-bromophenyliminomethoxalyl)-3,4-dihydrophenanthro[9,10-e]-1,2,3-triazin-2-ium-3-ide 6b, and 2,4-diphenyl-3a,6a-(biphen-2,2'-yl)-5,6-hexahydropyrrolo[2,3-d]-1,2, 3-triazol-2-ium-1-ide 11a.
• New phenanthrene systems: spiro-fused tricyclic phenanthro-1,2,4-triazolo-[4,3-d]-1,2,4-triazines and -[3,4-d]-1,2,5-oxadiazines: ring expansions of N-methylphenanthroazoliums
  作者：Richard N. Butler、John M. McMahon、Peter D. McDonald、Carmel S. Pyne、Simon Schambony、Patrick McArdle、Desmond Cunningham

  DOI：10.1039/a605770e

  日期：——

  New routes to substituted phenanthro[9,10-e]-1,2,4-triazines and phenanthro[9,10-c]-1,2,5-oxadiazines are described. Cycloadditions of these with C-phenyl-N-p-nitrophenylnitrile imide [IUPAC name: 2-benzylidene-1-(p-nitrophenyl)hydrazin-2-ium-1-ide] gave new substituted spiro-tricyclic phenanthro-1,2,4-triazolo[4,3-d][1,2,4]triazines and phenanthro-1,2,4-triazolo[3,4-d][1,2,5]oxadiazines. An X-ray crystal structure is reported on 7,10-diphenyl-5-(4′-nitrophenyl)-9,10-dihydro-5H-phenant hro[9,10-e][1,2,4]triazolo[4,3-d][1,2,4]triazine 5a.

  介绍了取代菲罗[9,10-e]-1,2,4-三嗪和菲罗[9,10-c]-1,2,5-恶二嗪的新路线。 这些化合物与 C-苯基-N-对硝基苯腈亚胺[IUPAC 名称：2-苄叉-1-(对硝基苯基)肼-2-鎓-1-ide]发生环加成反应，生成了新的取代的螺三环菲并-1,2,4-三唑并[4,3-d][1,2,4]三嗪和菲并-1,2,4-三唑并[3,4-d][1,2,5]恶二嗪。报告了 7,10-二苯基-5-（4′-硝基苯基）-9,10-二氢-5H-菲罗[9,10-e][1,2,4]三唑并[4,3-d][1,2,4]三嗪 5a 的 X 射线晶体结构。

表征谱图