1-benzyl-4-benzyloxypyridin-2(1H)-one | 108379-95-9

• 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: 1-benzyl-4-benzyloxypyridin-2(1H)-one
• 英文别名: 1-benzyl-4-benzyloxy-2(1H)-pyridone；1-benzyl-4-benzyloxy-2-pyridone；1-benzyl-4-(benzyloxy)pyridin-2(1H)-one；1-benzyl-4-benzyloxy-1H-pyridin-2-one；1-benzyl-4-phenylmethoxypyridin-2-one
• CAS: 108379-95-9
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: MPCPIBFZAKSVAX-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  531.3±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-benzyloxypyridin-2(1H)-one 在 5% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 1-benzyl-4-hydroxypyridin-2(1H)-one
  参考文献：
  名称：

  Design and synthesis of 2-pyridones as novel inhibitors of the Bacillus anthracis enoyl-ACP reductase

  摘要：

  Enoyl-ACP reductase (ENR), the product of the FabI gene, from Bacillus anthracis (BaENR) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis. A number of novel 2-pyridone derivatives were synthesized and shown to be potent inhibitors of BaENR. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.004
• 作为产物：
  描述：

  4-苄氧基-2(1H)-吡啶酮 、 溴甲苯 在 四丁基硫酸氢铵 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 1-benzyl-4-benzyloxypyridin-2(1H)-one
  参考文献：
  名称：

  Furanopyridine derivatives and methods of use

  摘要：

  本发明涉及具有一般式I的呋喃吡啶化合物，以及其立体异构体、互变异构体、溶剂合物、药学上可接受的盐和衍生物，以及其前药。该发明还包括包含一种式I化合物的药物组合物，调节Lck和ACK-1酶的方法，以及治疗各种相关疾病和症状的方法，包括炎症、T细胞激活抑制、增殖、关节炎、器官移植、缺血或再灌注损伤、心肌梗死、中风、多发性硬化、炎症性肠病、克罗恩病、狼疮、过敏、1型糖尿病、牛皮癣、皮炎、哈希蒙氏甲状腺炎、干燥综合征、自身免疫性甲状腺功能亢进症、艾迪生病、自身免疫性疾病、肾小球肾炎、过敏性疾病、哮喘、花粉热、湿疹、癌症、结肠癌、胸腺瘤等，在哺乳动物体内，包括向哺乳动物体内施用上述式I化合物的治疗有效量，并制备包含式I化合物的药物的方法。

  公开号：

  US20060046977A1

文献信息

• Iron catalyzed β-C(sp²)–H alkylation of enamides
  作者：Sylvain Bertho、Radhouan Maazaoui、Damla Torun、Ismaël Dondasse、Raoudha Abderrahim、Cyril Nicolas、Isabelle Gillaizeau

  DOI：10.1039/d1nj03673d

  日期：——

  An attractive and cheap alternative approach was developed for the β-C(sp2)–H (fluoro)alkylation of a range of cyclic and acyclic non-aromatic enamides using either FeCl2 as a catalyst or a stoichiometric amount of nontoxic iron powder. This reaction is regioselective and exhibits broad substrate scope and good functional group tolerance.

  开发了一种有吸引力且廉价的替代方法，用于使用 FeCl 2作为催化剂或化学计量量的无毒铁粉对一系列环状和非环状非芳香族烯酰胺进行β-C(sp 2 )–H (氟) 烷基化。该反应具有区域选择性，表现出广泛的底物范围和良好的官能团耐受性。
• SUBSTITUTED BICYCLIC HETEROARYL COMPOUNDS FOR THE TREATMENT OF CARDIOVASCULAR DISEASE
  申请人：Lampe Thomas

  公开号：US20100261736A1

  公开（公告）日：2010-10-14

  The present application relates to novel substituted bicyclic heteroaryl compounds, to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular diseases.

  本申请涉及新型取代的双环杂环芳基化合物，其制备方法，它们用于治疗和/或预防疾病的用途，以及它们用于制备治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防心血管疾病。
• Practical Pd/C-Catalysed Suzuki-Miyaura Reactions for the Preparation of 3-Aryl-4-oxypyridin-2(1<i>H</i>)-ones, 3-Aryl-2,4-oxypyridines and 3-Aryl-2,4-oxyquinolines as Useful Intermediates for the Synthesis of Biologically Active Compounds
  作者：Marc Lamblin、Hugo Bares、Jean Dessolin、Christel Marty、Nathalie Bourgougnon、François-Xavier Felpin

  DOI：10.1002/ejoc.201200721

  日期：2012.10

  4-oxypyridines, and 3-iodo-2,4-oxyquinolines with arylboronic acids are described as a useful and efficient alternative to homogeneous conditions. The methodology features ligand-free and environmentally friendly conditions, and tolerates a wide range of boronic acids. The cross-coupled products can be viewed as useful intermediates for the preparation of 3-aryl-4-hydroxypyridin-2(1H)-ones, which can be used

  3-iodo-4-oxypyridin-2(1H)-ones、3-iodo-2,4-oxypyridines 和 3-iodo-2,4-oxyquinolines 的实际多相 Pd/C 催化 Suzuki-Miyaura 交叉偶联反应芳基硼酸被描述为均相条件的有用且有效的替代方法。该方法的特点是无配体和环境友好的条件，并耐受广泛的硼酸。交叉偶联产物可被视为制备 3-芳基-4-羟基吡啶-2(1H)-酮的有用中间体，可用作抗疱疹剂的新核碱基。
• Furanopyridine derivatives and methods of use
  申请人：Nunes J. Joseph

  公开号：US20060046977A1

  公开（公告）日：2006-03-02

  The present invention relates to furanopyridine compounds having the general Formula I: and stereoisomers, tautomers, solvates, pharmaceutically acceptable salts and derivatives, and prodrugs thereof. The invention also includes pharmaceutical compositions comprising a compound of Formula I, methods of modulating Lck and ACK-1 enzymes and of treating various related diseases and conditions, including inflammation, inhibition of T cell activation, proliferation, arthritis, organ transplant, ischemic or reperfusion injury, myocardial infarction, stroke, multiple sclerosis, inflammatory bowel disease, Crohn's disease, lupus, hypersensitivity, type 1 diabetes, psoriasis, dermatitis, Hashimoto's thyroiditis, Sjogren's syndrome, autoimmune hyperthyroidism, Addison's disease, autoimmune diseases, glomerulonephritis, allergic diseases, asthma, hayfever, eczema, cancer, colon carcinoma, thymoma, just to name a few, in a mammal, comprising administering to the mammal a therapeutically effective amount a compound of Formula I, as described above, and methods of manufacturing medicaments comprising the compound of Formula I.

  本发明涉及具有一般式I的呋喃吡啶化合物，以及其立体异构体、互变异构体、溶剂合物、药学上可接受的盐和衍生物，以及其前药。该发明还包括包含一种式I化合物的药物组合物，调节Lck和ACK-1酶的方法，以及治疗各种相关疾病和症状的方法，包括炎症、T细胞激活抑制、增殖、关节炎、器官移植、缺血或再灌注损伤、心肌梗死、中风、多发性硬化、炎症性肠病、克罗恩病、狼疮、过敏、1型糖尿病、牛皮癣、皮炎、哈希蒙氏甲状腺炎、干燥综合征、自身免疫性甲状腺功能亢进症、艾迪生病、自身免疫性疾病、肾小球肾炎、过敏性疾病、哮喘、花粉热、湿疹、癌症、结肠癌、胸腺瘤等，在哺乳动物体内，包括向哺乳动物体内施用上述式I化合物的治疗有效量，并制备包含式I化合物的药物的方法。
• Palladium-Mediated Three-Component Synthesis of Furo[2,3-<i>b</i>]pyridones by One-Pot Coupling of 3-Iodopyridones, Alkynes, and Organic Halides
  作者：Emmanuel Bossharth、Philippe Desbordes、Nuno Monteiro、Geneviève Balme

  DOI：10.1021/ol034644y

  日期：2003.7.1

  [reaction: see text] The one-pot assembly of 4-alkoxy-3-iodo-2-pyridones, terminal alkynes, and organic halides has been achieved by integration of two sequential palladium-mediated cross-coupling reactions--Sonogashira and Wacker-type heteroannulation processes--and subsequent deprotection of the alkoxy group to afford furo[2,3-b]pyridones.

  [反应：参见文本]通过整合两个顺序的钯介导的交叉偶联反应（Sonogashira和Wacker），实现了4-烷氧基-3-碘-2-吡啶酮，末端炔烃和有机卤化物的一锅组装-型异环化过程-随后将烷氧基脱保护，得到呋喃[2,3-b]吡啶酮。