3,5-双(4-羟基苯基)吡啶 | 171980-66-8

• 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
• 中文名称: 3,5-双(4-羟基苯基)吡啶
• 英文名称: 4,4′-(pyridine-3,5-diyl)diphenol
• 英文别名: 4-[5-(4-hydroxyphenyl)-3-pyridyl]phenol；3,5-bis(4-hydroxyphenyl)pyridine；4,4'-(pyridine-3,5-diyl)diphenol；3,5-di(4-hydroxyphenyl)pyridine；Sch-21418；4-[5-(4-Hydroxyphenyl)pyridin-3-yl]phenol
• CAS: 171980-66-8
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: LVQSMYWNOMFDGX-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  478.5±35.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-双(4-羟基苯基)吡啶 在 三溴化硼 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-[4-[5-[4-(2-Hydroxyethoxy)phenyl]pyridin-3-yl]phenoxy]ethanol
  参考文献：
  名称：

  Synthesis of 2,5- and 3,5-diphenylpyridine derivatives for DNA recognition and cytotoxicity

  摘要：

  A series of 2,5- and 3,5-diphenylpyridine derivatives was synthetised in high yields. A versatile chemical strategy allows the design of diphenylpyridines differently substituted with cationic or neutral side chains. The interaction of the molecules with DNA was investigated by biophysical and biochemical methods and an AT-binder (20) was characterised. A few cytotoxic molecules were identified but their antiproliferative activity does not correlate with DNA binding. Two compounds 18 and 22 showed significant antiproliferative activity and provide a novel route to potential anticancer agents. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.011
• 作为产物：
  描述：

  DL-酪氨酸 在 碘 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以66%的产率得到3,5-双(4-羟基苯基)吡啶
  参考文献：
  名称：

  Molecular Iodine-Mediated Chemoselective Synthesis of Multisubstituted Pyridines through Catabolism and Reconstruction Behavior of Natural Amino Acids

  摘要：

  A new process has been developed for the selective construction of 2,6-disubstituted, 2,4,6-trisubstituted, and 3,5-disubstituted pyridines based on the catabolism and reconstruction behaviors of amino acids. Molecular iodine was used as a tandem catalyst to trigger the decarboxylation deamination of amino acids and to promote the subsequent formation of the pyridine products.

  DOI：

  10.1021/acs.orglett.5b03037

文献信息

• Redox-mediation of electron–electron spin–spin exchange interactions, | J |, in paramagnetic trinuclear molybdenum complexes: an example of a ‘J switch’
  作者：Elefteria Psillakis、Peter K. A. Shonfield、Abdel-Aziz Jouaiti、John P. Maher、Jon A. McCleverty、Michael D. Ward

  DOI：10.1039/a908323e

  日期：——

  A series of trinuclear molybdenum nitrosyl complexes has been prepared using the dinucleating ligands 4-(4-hydroxyphenyl)pyridine (HL1), 1-(4-pyridyl)-2-(4-hydroxyphenyl)-ethene (HL2) and -ethane (HL3), and the trinucleating ligands 3,5-bis(4-hydroxyphenyl)pyridine (H2L4) and 2,6-bis(4-ethenylpyridyl)-4-hydroxytoluene (HL5). These complexes are of the type [text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2] (text-decoration:underlineMo = Mo(NO)TpMe,Me, TpMe,Me = tris(3,5-dimethylpyrazolyl)borate; E = nothing, CHCH and CH2CH2; py = C5H4N or C5H3N; from HL1, HL2 and HL3), [Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl] (from H2L4), and [Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}] (from HL5). The species [text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2] contains one 16 valence electron (ve) ([text-decoration:underlineMoOC6H4–}2]) and two 17 ve centres ([(–py)text-decoration:underlineMoCl]), [Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl] has two 16 ([Cltext-decoration:underlineMoOC6H4–}]) and one 17 ([(–py)text-decoration:underlineMoCl]) ve centres and [Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}] one 16 and two 17 ve centres. Reduction of these species by cobaltocene in tetrahydrofuran/dichloromethane mixtures affords complexes having three 17 ve centres with one unpaired electron per metal centre. The interaction between these unpaired electrons in solution is determined by the relationship between |J|, the electron spin–spin exchange interaction, and AMo, the molybdenum hyperfine coupling constant, which was detected by EPR spectroscopy. In [text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2], the interaction was dependent on ligand conformation, |J| ≈ AMo when E = nothing, |J| ≫ AMo when E = CHCH and |J| ≪ AMo when E = CH2CH2. Reduction of [text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2] to [text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]− resulted in exchange between all three spins irrespective of ligand conformation, and the EPR spectra of [Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl]2− and [Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}]− were similar to that of [text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]−. Oxidation reconstitutes the original EPR spectra of [text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2], [Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl] and [Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}]. This behaviour is consistent with full three centre interaction being ‘switched on’ when the 17∶16∶17 or 16∶17∶16 ve systems are reduced to a 17∶17∶17 ve system, and ‘switched off’ on reoxidation.

  一系列三核钼硝酰配合物已经使用二核配体4-(4-羟基苯基)pyridine（HL1）、1-(4-吡啶基)-2-(4-羟基苯基)-乙烯（HL2）和-乙烷（HL3），以及三核配体3,5-二(4-羟基苯基)pyridine（H2L4）和2,6-二(4-乙烯基吡啶)-4-羟基甲苯（HL5）制备。这些配合物的类型为[text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]（text-decoration:underlineMo = Mo(NO)TpMe,Me, TpMe,Me = 三(3,5-二甲基吡唑基)硼酸盐；E = nothing, CHCH 和 CH2CH2；py = C5H4N 或 C5H3N；来源于HL1、HL2和HL3），[Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl]（来源于H2L4），以及[Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}]（来源于HL5）。该物种[text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]包含一个16价电子（ve）中心([text-decoration:underlineMoOC6H4–}2])和两个17价电子中心([(-py)text-decoration:underlineMoCl])，而[Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl]具有两个16价电子([Cltext-decoration:underlineMoOC6H4–}])和一个17价电子([(-py)text-decoration:underlineMoCl])中心，以及[Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}]具有一个16和两个17价电子中心。这些物种在四氢呋喃/二氯甲烷混合物中被羧基钴还原会生成具有三个17价电子中心和每个金属中心一个未成对电子的配合物。在溶液中，这些未成对电子之间的相互作用由|J|（电子自旋-自旋交换相互作用）与AMo（钼超细耦合常数）之间的关系决定，这种关系通过EPR光谱法得到检测。在[text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]中，相互作用依赖于配体构象，当E = nothing时，|J|≈AMo；当E = CHCH时，|J|≥AMo；当E = CH2CH2时，|J|≤AMo。从[text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]还原至[text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]⁻时，无论配体构象如何，所有三个自旋之间都发生了交换，而[Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl]⁻和[Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}]⁻的EPR光谱与[text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]⁻的光谱相似。氧化过程重新构造了[text-decoration:underlineMoOC6H4Epytext-decoration:underlineMoCl}2]、[Cltext-decoration:underlineMo(OC6H4)}2pytext-decoration:underlineMoCl]和[Cltext-decoration:underlineMoOC6H3Me[CHCHpytext-decoration:underlineMoCl]2}]的原始EPR光谱。这种行为与当17↓16↓17或16↓17↓16价电子体系被还原为17↓17↓17价电子体系时，完全的三中心相互作用被“开启”，而在重新氧化时则被“关闭”的情况相一致。
• Gyroscope-Like Platinum and Palladium Complexes with Trans-Spanning Bis(pyridine) Ligands
  作者：Paul D. Zeits、Giovanni Pietro Rachiero、Frank Hampel、Joseph H. Reibenspies、John A. Gladysz

  DOI：10.1021/om201145x

  日期：2012.4.9

  5-NC5H3(4-C6H4OH)2, Br(CH2)5CH═CH2, and Cs2CO3 yields 3,5-NC5H3(4-C6H4O(CH2)5CH═CH2)2 (8; 32%). Reactions of PtCl2 with 1a,b, 2a–e,h,i, 4a,b (but not 4c,d), 5a,c–f,h, and 8 afford the corresponding bis(pyridine) complexes trans-10a,b (40–12%), trans-12a–e,h,i (84–46%), trans-17a,b (88–22%), trans-19a,c–f,h (94–63%), and trans-22 (96%). Selected adducts are treated with Grubbs’ catalyst and then H2 (Pd/C) to

  制备具有一个或两个在乙烯基上终止的取代基的吡啶。反式-MCl 2加合物的分子内闭环复分解和氢化提供了标题化合物。Williamson醚合成使用醇HO（CH 2）Ñ CH = CH 2（Ñ = 1（一），2（b），3（Ç），4（d），5（ê），6（˚F），8 （h），9（i））和适当的卤化物可得到吡啶2-NC 5 H 4（CH 2 O（CH 2）Ñ CH = CH 2）（ 1A， b），3-NC 5 H ^ 4（CH 2 O（CH 2） Ñ CH = CH 2）（图2a - ë， ħ，我），和2,6- NC 5 ħ 3（CH 2 O（CH 2） ñ CH = CH 2） 2（图4a - d）在92-45％的产率。3,5-NC 5 H 3（COCl） 2与HO（CH 2）的反应Ñ CH = CH 2，得到二酯3,5- NC 5 H ^ 3（COO（CH 2） Ñ CH = CH 2） 2（ 5A
• Discovery of Small-Molecule Inhibitors of Ubiquitin Specific Protease 7 (USP7) Using Integrated NMR and in Silico Techniques
  作者：Paola Di Lello、Richard Pastor、Jeremy M. Murray、Robert A. Blake、Frederick Cohen、Terry D. Crawford、Joy Drobnick、Jason Drummond、Lorna Kategaya、Tracy Kleinheinz、Till Maurer、Lionel Rougé、Xianrui Zhao、Ingrid Wertz、Chudi Ndubaku、Vickie Tsui

  DOI：10.1021/acs.jmedchem.7b01293

  日期：2017.12.28

  oncology target for small molecule inhibitors. Herein we describe the biophysical, biochemical, and computational approaches that led to the identification of 4-(2-aminopyridin-3-yl)phenol compounds described by Kategaya ( Nature 2017, 550, 534–538) as specific inhibitors of USP7. Fragment based lead discovery (FBLD) by NMR combined with virtual screening and re-mining of biochemical high-throughput screening

  USP7是一种去泛素化酶，与稳定肿瘤抑制因子p53有关，因此，USP7作为小分子抑制剂的潜在肿瘤靶点已引起越来越多的关注。在本文中，我们描述了导致鉴定4-（2-氨基吡啶-3--3-基）苯酚化合物的生物物理，生物化学和计算方法。片谷（自然 2017年，550，534-538），为USP7的特异性抑制剂。通过NMR结合基于片段的铅发现（FBLD），虚拟筛选和生物化学高通量筛选（HTS）命中的再挖掘，发现了一系列结合在USP7催化域“棕榈”区域的配体并抑制其催化活性。然后通过基于结构的设计优化这些配体，以产生具有合理物理性质的细胞活性分子。该发现过程不仅涉及多种技术，而且还阐明了一种独特的方法，其中正交筛选方法的命中结果相互补充以进行潜在顾客识别。
• Iron-Mediated One-Pot Synthesis of 3,5-Diarylpyridines from β-Nitrostyrenes
  作者：Manda Sathish、Jadala Chetna、Namballa Hari Krishna、Nagula Shankaraiah、Abdullah Alarifi、Ahmed Kamal

  DOI：10.1021/acs.joc.5b02712

  日期：2016.3.4

  An operationally simple and mild one-pot protocol for the synthesis of a variety of 3,5-diarylpyridines from β-nitrostyrenes was achieved by using elemental iron. This reaction proceeds via reduction of the nitro group, resulting in in situ imine formation followed by trimolecular condensation with concomitant debenzylative aromatization. By employing this method, a series of symmetrical and unsymmetrical

  通过使用元素铁实现了一种从β-硝基苯乙烯合成各种3,5-二芳基吡啶的操作简单且温和的一锅操作方案。该反应通过硝基的还原进行，导致原位亚胺形成，随后三分子缩合并伴随脱苄基芳构化。通过采用这种方法，合成了一系列对称和不对称的3,5-二芳基吡啶，收率良好至极佳。此外，该方法还用于合成克级的消炎药Sch-21418。
• Polyethersulfone compositions
  申请人：Moore Roger David

  公开号：US20060030683A1

  公开（公告）日：2006-02-09

  Novel polyethersulfone compositions have been discovered which incorporate structural subunits derived from sulfonated bis(halophenyl)sulfones, dihydroxy terphenyls, and/or bis(hydroxyphenyl)pyridines. The sulfonated polyethersulfones show promise as materials for use in polymer electrolyte membranes (PEMs) in fuel cells owing to their high proton conductivities (0.02-0.07 S/cm at 20° C. and 100 percent humidity). In addition, a novel unsulfonated thermoplastic polyethersulfone comprising structural subunits derived from a non-sulfonated bis(halophenyl)sulfone bis4-fluorophenyl)sulfone and 4,4′-dihydroxyphenyl-2,6-pyridine (CAS No. 171820-16-9) is disclosed.

  人们发现了新型聚醚砜组合物，其中包含的结构单元来自磺化双（卤苯基）砜、二羟基三联苯和/或双（羟基苯基）吡啶。磺化聚醚砜具有很高的质子传导性（在 20° C 和 100% 湿度条件下为 0.02-0.07 S/cm），因此有望用作燃料电池中的聚合物电解质膜（PEM）材料。此外，还公开了一种新型非磺化热塑性聚醚砜，该聚醚砜由衍生自非磺化双（卤苯基）砜双4-氟苯基）砜和 4,4′-二羟基苯基-2,6-吡啶（化学文摘社编号：171820-16-9）的结构单元组成。