6-(hydroxymethyl)-2,2'-bipyridine | 149775-41-7

• 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: 6-(hydroxymethyl)-2,2'-bipyridine
• 英文别名: 2,2'-bipyridin-6-ylmethanol；[2,2'-Bipyridin]-6-ylmethanol；(6-pyridin-2-ylpyridin-2-yl)methanol
• CAS: 149775-41-7
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: FHSYXEVCRNGPHH-UHFFFAOYSA-N

物化性质

• 沸点：
  348.5±32.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  6-甲基-2,2′-二吡啶	6-methyl-2,2'-bipyridine	56100-22-2	C11H10N2	170.214
  ——	(6-(2-pyridyl)-2-pyridyl)methyl acetate	82740-75-8	C13H12N2O2	228.25
  2,2'-联吡啶-6-甲酸甲酯	2,2'-dipyridyl-6-carboximidic acid methyl ester	203573-76-6	C12H10N2O2	214.224
  6-氰基-2,2'-联吡啶	2,2'-bipyridyl-6-carbonitrile	4392-85-2	C11H7N3	181.197
  6-(溴甲基)-2,2'-联吡啶	6-bromomethyl-2,2'-bipyridine	83478-63-1	C11H9BrN2	249.11
  [2,2-联吡啶]-6-甲醛	6-formyl-2,2'-bipyridine	134296-07-4	C11H8N2O	184.197
  ——	4-(methylthio)-6-methyl-2,2'-bipyridinyl	99112-37-5	C12H12N2S	216.307
  2,2'-联吡啶	[2,2]bipyridinyl	366-18-7	C10H8N2	156.187

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6-(chloromethyl)-2,2'-bipyridine	82740-65-6	C11H9ClN2	204.659
  6-(溴甲基)-2,2'-联吡啶	6-bromomethyl-2,2'-bipyridine	83478-63-1	C11H9BrN2	249.11
  [2,2-联吡啶]-6-甲醛	6-formyl-2,2'-bipyridine	134296-07-4	C11H8N2O	184.197
  ——	di[(2,2'-bipyridin-6-yl)methyl] 3,3'-dithiodipropanoate	——	C28H26N4O4S2	546.671
  ——	2-(6-Pyridin-2-ylpyridin-2-yl)acetonitrile	203573-77-7	C12H9N3	195.224
  ——	N-[([2,2'-bipyridin]-6-yl)methylidene]hydroxylamine	——	C11H9N3O	199.212

反应信息

• 作为反应物：
  描述：

  6-(hydroxymethyl)-2,2'-bipyridine 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-(6-Pyridin-2-ylpyridin-2-yl)acetonitrile
  参考文献：
  名称：

  Regioselective Functionalization of 2,2'-Bipyridine and Transformations into Unsymmetric Ligands for Coordination Chemistry.

  摘要：

  Novel synthetic strategies for a series of unsymmetrically substituted 2,2'-bipyridines have been developed. These bipyridines have found use in some novel homoleptic and heteroleptic ruthenium(II) complexes. Two methods for regiochemical control of nucleophilic addition to bpy have been explored: (i) mono N-oxidation followed by cyanation and subsequent hydrolysis gave 6-carboxy-2,2'-bipyridine (4); (ii) mono N-methylation followed by the conversion into 6-bromo-2,2'-bipyridine (12) and subsequent nucleophilic addition of lithio-acetonitrile followed by hydrolysis of 6-cyanomethyl-2,2'-bipyridine (8) gave the homologous 2,2'-bipyridine-6-acetic acid (9). An established method of regioselective mono-ring alkylation of bpy using methyllithium yielded 6-methyl-2,2'-bipyridine (14), and the generation of the anion of 14 and subsequent addition to a chloromethyl oxazoline was applied to synthesize a second homologue, methyl 2,2'-bipyridine-6-propanoate (16). Structural determinations using H-1, C-13 and 2D NMR spectroscopy permitted complete assignments of all signals in the H-1 NMR spectra.

  DOI：

  10.3891/acta.chem.scand.52-0077
• 作为产物：
  描述：

  2-(三甲基甲锡烷基)吡啶 在 bis-triphenylphosphine-palladium(II) chloride lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 6-(hydroxymethyl)-2,2'-bipyridine
  参考文献：
  名称：

  二硫键官能化的3、4、5和6取代的2,2'-联吡啶及其钌配合物。

  摘要：

  DOI：

  10.1021/jo9814795

文献信息

• C_sp2–Br bond activation of Br-pyridine by neophylpalladacycle: formation of binuclear seven-membered palladacycle and bipyridine species
  作者：Juan Nicasio-Collazo、Katarzyna Wrobel、Kazimierz Wrobel、Oracio Serrano

  DOI：10.1039/c7nj02468a

  日期：——

  In this work, the synthesis and reactivity of seven-membered palladacycles are described, and a novel bi-pyridines synthesis in a catalytic pathway is reported. Neophylpalladacycle (I) reacts with an excess of 2-Br-pyridine, giving the desired new binuclear seven-membered palladacycle (1) and unexpectedly, a bipyridine complex [Pd(BiPy)Br2]. ESI-HRMS experiments show that fragmentation into the Pd-Br

  在这项工作中，描述了七元的palladacycles的合成和反应性，并报道了催化途径中的新型联吡啶合成。新叶新戊四环（I）与过量的2-Br-吡啶反应，得到所需的新双核七元帕拉四环（1），并出乎意料地得到联吡啶复合物[Pd（BiPy）Br 2 ]。ESI-HRMS实验表明，1上的Pd-Br键断裂会发生，从而产生异常的两个配位的Pd（II）分子离子。[Pd（NeoPyR）] +。
• CXCR4 chemokine receptor binding comounds
  申请人：——

  公开号：US20040209921A1

  公开（公告）日：2004-10-21

  The present invention relates to compounds that bind to chemokine receptors, and having the formula 1 wherein each A, X, Y, R 1 , R 2 and R 3 are substituents. The present invention also relates to methods of using such compounds, such as in treating HIV infection and inflammatory conditions such as rheumatoid arthritis. Furthermore, the present invention relates to methods to elevate progenitor and stem cell counts, as well as methods to elevate white blood cell counts, using such compounds.

  本发明涉及与趋化因子受体结合的化合物，其具有式1的结构，其中A、X、Y、R1、R2和R3均为取代基。本发明还涉及使用这类化合物的方法，例如在治疗HIV感染和炎症性疾病如类风湿性关节炎中的应用。此外，本发明还涉及使用这类化合物来提高祖细胞和干细胞计数的方法，以及提高白细胞计数的方法。
• Optically Active Helical Lanthanide Complexes: Storable Chiral Lewis Acidic Catalysts for Enantioselective Diels–Alder Reaction of Siloxydienes
  作者：Shinji Harada、Saki Nakashima、Shihori Sekino、Wakana Oishi、Atsushi Nishida

  DOI：10.1002/asia.201901705

  日期：2020.2.17

  Lanthanide triflates and a series of hexadentate chiral ligand complexes were synthesized. X‐ray‐quality crystals were obtained from mixtures of the lanthanide complexes, which were helical in shape. The complexes showed Lewis acidity and catalyzed the enantioselective Diels–Alder reaction of electron‐rich siloxydienes. The complexes were stable enough to be stored at ambient temperature on a laboratory

  合成了镧系元素三氟甲磺酸酯和一系列六齿手性配体配合物。X射线质量的晶体是从镧系元素络合物的混合物中获得的，这些化合物呈螺旋状。络合物显示路易斯酸度，并催化富电子的甲硅烷氧基二烯的对映选择性Diels-Alder反应。配合物足够稳定，可以在室温下在实验室的工作台上储存，即使一个月后仍保持其路易斯酸度。
• Ipso substitution of 2-alkylsulfinylpyridine by 2-pyridyllithium; a new preparation of oligopyridine and their bromomethyl derivatives
  作者：Junichi Uenishi、Takakazu Tanaka、Shoji Wakabayashi、Shigeru Oae、Hiroshi Tsukube

  DOI：10.1016/s0040-4039(00)97692-5

  日期：1990.1

  Unsymmetrical and symmetrical 2,2′-bipyridines 5 and 6 have been prepared. The methods applied are new and offer efficient syntheses of higher oligopyridines and their bromomethyl derivatives.

  已经制备了不对称和对称的2,2'-联吡啶5和6。所应用的方法是新方法，可提供高级寡吡啶及其溴代甲基衍生物的有效合成方法。
• [EN] IMMUNOSUPPRESSIVE AGENTS<br/>[FR] AGENTS IMMUNOSUPPRESSEURS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2018134847A1

  公开（公告）日：2018-07-26

  Provided herein is a compound having the Formula 1, all of its related stereoisomers and their pharmaceutically acceptable salts with immunosuppressive property and process for preparation thereof. The said molecule provides potent anti-proliferative activity in lymphocyte proliferation assay and in mouse skin graft rejection assay. Further, the said molecule is a valuable lead compound in development of improved immunosuppressive agents.

  本文提供的是具有化学式1的化合物，以及其所有相关立体异构体和具有免疫抑制性质的药用盐，以及其制备方法。所述分子在淋巴细胞增殖实验和小鼠皮肤移植排斥实验中表现出强大的抗增殖活性。此外，所述分子是开发改进的免疫抑制剂中的有价值的先导化合物。