3-Benzylpyridin-N-oxid | 32361-74-3

• 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: 3-Benzylpyridin-N-oxid
• 英文别名: 3-Benzylpyridine N-oxide；3-benzyl-1-oxidopyridin-1-ium
• CAS: 32361-74-3
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: OBSYYVZIHSMIAR-UHFFFAOYSA-N

物化性质

• 沸点：
  383.1±11.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Benzylpyridin-N-oxid 在 <4-CH3OC6H4P(S)S>2 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 7.75h， 生成 3-benzylpyridine-2-thione
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051
• 作为产物：
  描述：

  (E)-acrylaldehyde O-(1-phenylprop-2-yn-1-yl)oxime 在 CuBr(PPh₃)₃ 、 三苯基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以80%的产率得到3-Benzylpyridin-N-oxid
  参考文献：
  名称：

  Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in (E)-O-Propargylic α,β-Unsaturated Oximes

  摘要：

  Cu-catalyzed cyclizations of (E)-O-propargylic oximes of alpha,B-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh(3))(3) (10 mol %) and PPh(3) (10 mol %) in DMSO at 120 degrees C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6 pi-3-azatriene electrocyclization.

  DOI：

  10.1021/ja102436z

文献信息

• 2-substituted piperidines, pyrrolidines and hexahydro-1H-azepines
  申请人：Merck & Co., Inc.

  公开号：US05494919A1

  公开（公告）日：1996-02-27

  The present invention is directed to certain piperidine, pyrrolidine, and hexahydro-1H-azepine compounds of the general structural formula: ##STR1## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.5, A, W, X, Y, and n axe as defined herein. These compounds promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which s are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such compounds as the active ingredient thereof are also disclosed.

  本发明涉及某些哌啶、吡咯啉和六氢-1H-氮杂环烃化合物，其一般结构式如下：其中R.sub.1、R.sub.3、R.sub.4、R.sub.5、A、W、X、Y和n如本文所定义。这些化合物促进人类和动物体内生长激素的释放。这种特性可用于促进食用动物的生长，使可食肉制品的生产更加高效，在人类中，可用于治疗生长激素分泌不足所导致的生理或医学状况，如生长激素缺乏儿童的矮小身材，并治疗通过生长激素的合成效应改善的医学状况。还公开了含有这些化合物作为活性成分的促生长激素释放组合物。
• [EN] PIPERIDINES, PYRROLIDINES AND HEXAHYDRO-1H-AZEPINES PROMOTE RELEASE OF GROWTH HORMONE<br/>[FR] PIPERIDINES, PYRROLIDINES ET HEXAHYDRO-1H-AZEPINES FAVORISANT LA LIBERATION DE L'HORMONE DE CROISSANCE
  申请人：MERCK & CO., INC.

  公开号：WO1995013069A1

  公开（公告）日：1995-05-18

  (EN) The present invention is directed to certain piperidine, pyrrolidine, and hexahydro-1H-azepine compounds of general structural formula (I) wherein R1, R3, R4, R5, A, W, X, Y, and n are as defined herein. These compounds promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such compounds as the active ingredient thereof are also disclosed.(FR) L'invention concerne certains composés de pipéridine, de pyrrolidine, et d'hexahydro-1H-azépine de formule structurale (I) dans laquelle R1, R3, R4, R5, A, W, X, Y et n sont définis dans la description. Ces composés favorisent la libération de l'hormone de croissance chez les humains et les animaux. Cette propriété peut être utilisée pour favoriser la croissance d'animaux destinés à l'alimentation et augmenter la production de produits de viande comestibles, et, chez les humains, pour traiter des états physiologiques ou médicaux caractérisés par une insuffisance de sécrétion de l'hormone de croissance telle que l'insuffisance staturale chez l'enfant, et traiter des états médicaux pouvant être améliorés par les effets anabolisants de l'hormone de croissance. L'invention porte également sur des compositions libérant l'hormone de croissance dans lesquelles lesdits composés sont utilisés comme principes actifs.

  本发明涉及通式（I）中R1、R3、R4、R5、A、W、X、Y和n所定义的某些哌啶、吡咯烷和六氢-1H-氮杂环化合物。这些化合物促进人类和动物的生长激素释放。这种特性可用于促进食用动物的生长，使可食肉类产品的生产更加高效，以及在人类中，用于治疗生长激素分泌不足所表现出的生理或医学状况，例如生长激素缺乏症儿童的矮小症，以及治疗通过生长激素的合成代谢作用得到改善的医学状况。还公开了含有该化合物作为活性成分的生长激素释放组合物。
• Substituted pyridines as dopamine-beta-hydroxylase inhibitors
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0308159A2

  公开（公告）日：1989-03-22

  Compounds of formula in which X¹ to X⁵ are hydrogen, halogen, hydroxy or alkoxy and n is 1 to 5, processes for their preparation intermediates useful in their preparation, pharmaceutical compositions containing them and their use in therapy in particular as dopamine-β-hydroxylase inhibitors.

  式化合物 其中 X¹ 至 X⁵ 为氢、卤素、羟基或烷氧基且 n 为 1 至 5 的化合物、用于制备它们的中间体的制备工艺、含有它们的药物组合物以及它们在治疗中的用途，特别是作为多巴胺-β-羟化酶抑制剂。
• Barchiesi, Emma; Bradamante, Silvia; Carfagna, Carla, Journal of the Chemical Society. Perkin transactions II, 1987, p. 1009 - 1014
  作者：Barchiesi, Emma、Bradamante, Silvia、Carfagna, Carla、Ferraccioli, Raffaella、Giorgio, A.、Pagni, Giorgio A.

  DOI：——

  日期：——
• EP0739204A4
  申请人：——

  公开号：EP0739204A4

  公开（公告）日：2000-03-15