4-(3,4-dimethoxyphenyl)pyridine | 39795-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(3,4-dimethoxyphenyl)pyridine
• CAS: 39795-63-6
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: VQSAZLNDWODBDE-UHFFFAOYSA-N

物化性质

• 沸点：
  325.5±32.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,4-dimethoxyphenyl)pyridine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以99 %的产率得到Pyridine, 4-[4,5-dihydroxyphenyl]-
  参考文献：
  名称：

  菱角样小分子解毒剂可在体内中和普通肝素和低分子量肝素

  摘要：

  普通肝素（UFH）和低分子肝素（LMWH）广泛应用于外科手术和体外治疗，但存在出血风险。鱼精蛋白是唯一临床批准的解毒剂，可以完全中和UFH，但只能部分中和LMWH，并且还存在许多安全缺陷。在这里，我们证明了菱角状多阳离子小分子可以完全中和 UFH 和 LMWH。血浆和全血的体外和离体测定以及小鼠和大鼠的体内测定表明，先导化合物不仅表现出更高的中和活性和更宽的治疗窗，优于鱼精蛋白，而且具有生物相容性。先导化合物在小鼠中的有效中和剂量和最大耐受剂量分别确定为 0.4 和 25 mg/kg，这表明进一步的临床前研究具有良好的前景。

  DOI：

  10.1021/acs.jmedchem.3c02224
• 作为产物：
  描述：

  4,4-哌啶二醇 在 palladium on activated charcoal 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 邻二甲苯 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 65.0h， 生成 4-(3,4-dimethoxyphenyl)pyridine
  参考文献：
  名称：

  Synthesis and dihydropteridine reductase inhibitory effects of potential metabolites of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine

  摘要：

  1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a nigrostriatal neurotoxin which can cause irreversible parkinsonism in humans and primates by selective destruction of neurons in the substantia nigra. It is possible that MPTP could be metabolized by hydroxylation of the phenyl ring and/or aromatization of its nitrogen-containing ring. Hydroxylated derivatives of 4-phenyl-1,2,3,6-tetrahydropyridine, 4-phenylpiperidine, and 4-phenylpyridine were synthesized and tested in vitro as inhibitors of dihydropteridine reductase (DHPR) from human liver and rat striatal synaptosomes. It was found that all hydroxy derivatives were about 100-10 000 times more inhibitory than MPTP to DHPR. The inhibitory potency of the hydroxylated derivatives increased with the number of hydroxyl substitutions present on the phenyl ring (catechol greater than phenol) and with oxidation of the nitrogen-containing ring (pyridine greater than tetrahydropyridine greater than piperidine).

  DOI：

  10.1021/jm00381a009

文献信息

• Programmable Self-Assembly of Heterometallic Palladium(II)-Copper(II) 1D Grid-Chain using Dinuclear Palladium(II) Corners with Pyrazole-Carboxylic Acid Ligands
  作者：Wen-Qing Sun、Jin Tong、Hong-Lin Lu、Ting-Ting Ma、Hong-Wei Ma、Shu-Yan Yu

  DOI：10.1002/asia.201701766

  日期：2018.5.4

  A novel heterometallic diPdII–diCuII grid‐chain, [(bpy)4Pd4Cu2L4](NO3)4}n (2; bpy=2,2′‐bipyridine), was synthesized through a programmable self‐assembly approach from the molecular corners [(bpy)2Pd2(HL)(L)](NO3) (1) as linkers with CuII nitrate by using the bifunctional H2L ligand featuring primary (pyrazole) and secondary (benzoic acid) groups. Structural analysis revealed that 1D structure 2 consists

  通过可编程序程序合成了一种新型的杂金属diPd II –diCu II网格链[（（bpy）4 Pd 4 Cu 2 L 4 ]（NO 3）4 } n（2 ; bpy = 2,2'-联吡啶）分子角[[bpy）2 Pd 2（HL）（L）]（NO 3）（1）作为连接剂与硝酸铜II的连接，方法是使用具有伯（吡唑）和仲酸的双功能H 2 L配体（苯甲酸）基团。结构分析表明1D结构2由一个[Cu 2（O 2 CPh）4 ] n单元作为桥和两个[（bpy）2 Pd 2 L 2 ] n角构成。此外，进一步探讨了使用2对杂金属协同作用对Suzuki偶联反应的催化作用。
• Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1002/ejoc.201402455

  日期：2014.8

  Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot

  公开了在 Pd 催化条件下使用溴吡啶和溴喹啉与三芳基铋作为亚化学计量量的三重偶联试剂的交叉偶联研究。与单-和二溴吡啶基底物的反应性很高，并且单-和双-偶联是区域选择性地进行的。以高产率形成了单芳基和二芳基吡啶库。一锅法提供了对称和不对称二芳基吡啶的简单直接合成。使用三芳基铋试剂实现了 2-溴和 3-溴喹啉的芳基化。该研究表明，三芳基铋可用作三重芳基化试剂，用于在 Pd 催化条件下通过与溴吡啶和溴喹啉偶联合成芳基吡啶和喹啉。
• Synthesis of analogs of amrinone: 4-(3,4-Disubstitutedphenyl)pyridines and derivatives thereof
  作者：Baldev Singh、George Y. Lesher

  DOI：10.1002/jhet.5570280416

  日期：1991.6

  4-(3,4-Dimethoxyphenyl)pyridine (5c) prepared by the coupling of 3,4-dimethoxyphenyldiazonium chloride with pyridine was converted to 4-(4-pyridinyl)benzene-1,2-diol (6c) by treating with hydrobromic acid. Diazotization of 4-(4-pyridinyl)benzeneamine (7) and 3-(4-pyridinyl)benzeneamine (12) gave the corresponding phenols 8 and 13 which were nitrated to give 2-nitro-4-(4-pyridinyl)phenol (9) and 2-

  通过将3,4-二甲氧基苯基重氮氯化物与吡啶偶联制备的4-（3,4-二甲氧基苯基）吡啶（5c）通过氢溴酸处理转化为4-（4-吡啶基）苯-1,2-二醇（6c）酸。4-（4-吡啶基）苯胺（7）和3-（4-吡啶基）苯胺（12）重氮化，得到相应的酚8和13，将其硝化得到2-硝基-4-（4-吡啶基）苯酚（7）。9）和2-硝基-5-（4-吡啶基）-苯酚（14）。还原这些硝基苯酚得到相应的氨基苯酚10和16，它们再与N，N'反应-羰基二咪唑分别生成苯并恶唑酮11和17。催化还原2-硝基-4-（4-吡啶基）苯胺（18），得到4-（4-吡啶基）苯-1,2-二胺（19），使其与原酸酯，尿素，四乙氧基甲烷和N，N反应-二（羰甲氧基）甲基伪硫脲，得到相应的苯并咪唑衍生物20、21、22和23。
• The Palladium Catalysed Suzuki Coupling of 2- and 4-Chloropyridines
  作者：Olivier Lohse

  DOI：10.1055/s-1999-2533

  日期：1999.1
• Spin-Crossover and Liquid Crystal Properties in 2D Cyanide-Bridged Fe^II−M^I/II Metalorganic Frameworks
  作者：M. Seredyuk、A. B. Gaspar、V. Ksenofontov、Y. Galyametdinov、M. Verdaguer、F. Villain、P. Gütlich

  DOI：10.1021/ic101304v

  日期：2010.11.1

  Novel two-dimensional heterometallic Fe(II) M(Ni-II, Pd-II, Pt-II and Ag-I, and Au-I) cyanide-bridged metalorganic frameworks exhibiting spin-crossover and liquid crystal properties, formulated as FeL2[M-I/II(CN)(x)](y)} . sH(2)O, where L are the ligands 4-(4-alkoxyphenyl)pyridine, 4-(3,4-dialkoxyphenyl)pyridine, and 4-(3,4,5-trisalkoxyphenyl)pyridine, have been synthesized and characterized. The physical characterization has been carried out by means of EXAFS, X-ray powder diffraction, magnetic susceptibility, differential scanning measurements, and Mossbauer spectroscopy. The 2D Fe(II) metallomesogens undergo incomplete and continuous thermally induced spin transition at T-1/2 approximate to 170 K and crystal-to-smectic transition above 370 K.