(4-methoxyphenyl)-pyridin-2-yldiazene | 79917-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-methoxyphenyl)-pyridin-2-yldiazene
• 英文别名: 2-<(p-methoxyphenyl)azo>pyridine；2-(p-methoxyphenyl)azopyridine；2-(4-methoxy-phenylazo)-pyridine；2-(4-Methoxy-phenylazo)-pyridin
• CAS: 79917-49-0
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: DOFFHXJRDOMZHS-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)-pyridin-2-yldiazene 在 盐酸 作用下， 以 乙腈 为溶剂， 以64%的产率得到C₁₂H₁₀N₃O⁽¹⁺⁾*Cl^(1-)
  参考文献：
  名称：

  Mild Synthesis of a Family of Planar Triazinium Cations via Proton-Assisted Cyclization of Pyridyl Containing Azo Compounds and Studies on DNA Intercalation

  摘要：

  An efficient synthesis of a family of heteroaromatic triazinium compounds, [2a]X-[2g]X (X= Cl, ClO4, NO3, and HSO4), from 2-(arylazo)pyridines via proton-catalyzed heterocyclization is described. Characterization of the compounds is made by different spectroscopic, electrochemical techniques, as well as single-crystal structure determination of the triflate salt of a representative compound, [2a]CF3SO3. The bond parameters indicate that the tricyclo compound, 2a(+), is planar and aromatic with a N-N bond length of 1.275(6) angstrom. These exhibited fluorescence with an emission maximum in the range of 540-535 nm with moderate quantum yields. The triazinium salts can be reduced in two successive one-electron steps as probed by cyclic voltammetry and coulometry. The paramagnetic radical intermediate 2a(center dot) is distinguished by a sharp and intense EPR spectrum. Fluorescence spectroscopy, circular dichroism, cyclic voltammetry, viscosity measurements, together with DNA melting studies have been used to characterize the binding of 2a+ with calf thymus DNA. The emission quenching of the compound by [Fe(CN)(6)](4-) decreased when bound to DNA. As determined by a MTT assay, 2a+ exhibited significant cytotoxicity at a higher concentration range of 1 mg/mL to 1 mu g/mL; however, the % survival ratio increased with dilution. Cellular uptake studies of the referenced compound were followed by FACS analysis.

  DOI：

  10.1021/ja710211u
• 作为产物：
  描述：

  S,S-dimethyl-N-(2-pyridyl)sulfilimine 在 二甲基硫 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (4-methoxyphenyl)-pyridin-2-yldiazene
  参考文献：
  名称：

  Conversion of a primary amino group into a nitroso group. Synthesis of nitroso-substituted heterocycles

  摘要：

  DOI：

  10.1021/jo00342a035

文献信息

• [EN] CATIONIC DIRECT DYES<br/>[FR] COLORANTS DIRECTS CATIONIQUES
  申请人：BASF SE

  公开号：WO2016146813A1

  公开（公告）日：2016-09-22

  The invention relates to cationic direct dyes of the formula I (1), wherein m and n are independently from each other 0 or 1, D is an aromatic or a cationic heteroaromatic group, which are further specified, K is an aromatic or heteroaromatic group, E1 and E2 are independently from each other =CH- or =N-, An is an anion and a is a number from 1 to 6 and R1 and R2 are independently from each other and further specified. The compounds show washfastness at hair-dying.

  这项发明涉及公式I（1）的阳离子直接染料，其中m和n分别独立于0或1，D是芳香或阳离子杂芳基，进一步具体说明，K是芳香或杂芳基，E1和E2分别独立于=CH-或=N-，An是阴离子，a是1到6之间的数字，R1和R2分别独立于彼此并进一步具体说明。这些化合物在染发时表现出良好的耐洗性。
• The Preparation of Pyridine Azo Compounds¹
  作者：Robert W. Faessinger、Ellis V. Brown

  DOI：10.1021/ja01154a031

  日期：1951.10
• TAYLOR, E. C.;TSENG, CHI-PING;RAMPAL, J. B., J. ORG. CHEM., 1982, 47, N 3, 552-555
  作者：TAYLOR, E. C.、TSENG, CHI-PING、RAMPAL, J. B.

  DOI：——

  日期：——
• CATIONIC DIRECT DYES
  申请人：BASF SE

  公开号：EP3271423A1

  公开（公告）日：2018-01-24
• Cationic Direct Dyes
  申请人：BASF SE

  公开号：US20180244924A1

  公开（公告）日：2018-08-30

  The invention relates to cationic direct dyes of the formula I (1), wherein m and n are independently from each other 0 or 1, D is an aromatic or a cationic heteroaromatic group, which are further specified, K is an aromatic or heteroaromatic group, E 1 and E 2 are independently from each other ═CH— or ═N—, An is an anion and a is a number from 1 to 6 and R 1 and R 2 are independently from each other and further specified. The compounds show washfastness at hair-dying.