1-[2-oxo-2-(phenyl)ethyl]-4-methylpyridinium chloride | 105757-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-oxo-2-(phenyl)ethyl]-4-methylpyridinium chloride
• 英文别名: 1-[2-oxo-2(phenyl)ethyl]-4-methylpyridinium chloride；1-phenacyl-4-methylpyridinium chloride；4-methyl-1-phenacylpyridinium chloride；4-Methyl-1-(2-oxo-2-phenylethyl)pyridin-1-ium chloride；2-(4-methylpyridin-1-ium-1-yl)-1-phenylethanone;chloride
• CAS: 105757-72-0
• 化学式: C₁₄H₁₄NO*Cl
• 分子量: 247.724
• InChiKey: RAZNQXLYLHVKNB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-oxo-2-(phenyl)ethyl]-4-methylpyridinium chloride 在 sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 生成 (Z)-ethoxy-[4-(4-methylpyridin-1-ium-1-yl)-3-phenyl-5-sulfanylidenethiophen-2-ylidene]methanolate
  参考文献：
  名称：

  新的氮桥杂环的制备。16. Thieno [2,3-b] indolizine 衍生物的简易合成

  摘要：

  2-乙氧基羰基-3-甲基-和3-苯基噻吩并[2,3-b]吲哚嗪衍生物首先通过处理三环5,5a-二氢吡啶并[2,1-c]噻吩并[3, 2-e][1,4] 噻嗪与脱氢剂。与双环1,9a-二氢吡啶并[2,1-c][1,4]噻嗪的情况相比，这里得到的所有噻吩并吲哚茚都是重排产物，没有得到脱硫产物。

  DOI：

  10.1246/bcsj.60.3713
• 作为产物：
  描述：

  4-甲基吡啶 、 alpha-氯乙酰苯 反应 24.0h， 以85%的产率得到1-[2-oxo-2-(phenyl)ethyl]-4-methylpyridinium chloride
  参考文献：
  名称：

  Synthesis and biological evaluation of a new series of N-ylides as protein farnesyltransferase inhibitors

  摘要：

  A new family of 30 benzoylated N-ylides 4 and 5 was synthesized and evaluated for the inhibitory activity on human protein farnesyltransferase. Most of these novel compounds possessed in vitro inhibition potencies in the micromolar range. The nature of the substituents on the pyridine and phenyl units proved to be important in determining inhibitory activity and generally, the replacement of the cyanoacrylonitrile function by a cyanoethylacrylate group decreased the biological potential on farnesyltransferase. These results completed our SAR study on this original class of N-ylides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.088

文献信息

• Preparation of New Nitrogen-Bridged Heterocycles. 60. Syntheses and Conformational Analyses of Bis(indolizin-1-yl) Disulfides
  作者：Akikazu Kakehi、Hiroyuki Suga、Hiroko Okuno、Masaki Okuhara、Akira Ohta

  DOI：10.1248/cpb.55.1458

  日期：——

  hence, of a particular gauche (cis) conformation. However, the conformational considerations and molecular calculations (Mopac PM3) for some bis(indolizin-1-yl) disulfides showed the presence of four more stable gauche forms in which two are enantiomeric, resulting in three types of gauche structures. These three types of gauche structures were confirmed by X-ray analyses.

  制备了一些易于从哌啶处理1-（苯甲酰硫基）吲哚并二嗪的双（吲哚并-1-基）二硫化物，并研究了它们的构象。与1-（苯甲酰硫基）吲哚并咪唑相比，这些二硫化物的（1）H-NMR光谱在每个吡啶环质子上显示出相当高的场位移（δ0.13-0.82 ppm），UV光谱显示出显着的红移和高色移。这些结果有力地支持了这些分子中两个吲哚嗪环之间的分子内pi-pi相互作用的参与，因此也支持了特定的gauche（cis）构象。但是，某些双（吲哚并嗪-1-基）二硫化物的构象考量和分子计算（Mopac PM3）显示存在四种更稳定的薄纱形式，其中两种是对映体，产生三种类型的薄纱结构。X射线分析证实了这三种类型的薄纱结构。
• Preparation of New Nitrogen-Bridged Heterocycles. 42. Synthesis and the Reaction of Pyridinium<i>N</i>-Ylides Using Bifunctional Ethyl Thiocyanatoacetates
  作者：Akikazu Kakehi、Suketaka Ito、Yasunobu Hashimoto

  DOI：10.1246/bcsj.69.1769

  日期：1996.6

  cycloadditions of some pyridinium (unsymmetrically substituted cyanomethylide)s with dimethyl acetylenedicarboxylate (DMAD) in various solvents afforded only dimethyl 3-cyanoindolizine-1,2-dicarboxylate, except a few examples. On the other hand, the treatment of pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates with a strong base, such as potassium t-butoxide, gave new bicyclic mesoionic compounds

  各种吡啶鎓（单取代的甲基化物）在硫氰酸乙酯或 2-硫氰酸根合丙酸乙酯中顺利地攻击氰基，以低到中等的产率得到相应的吡啶鎓（取代的氰基甲基化物），而吡啶鎓（未取代的酰胺化物）与在相同的试剂中酯羰基以可观的产率得到吡啶鎓（硫氰酸根合乙酰基）-或（2-硫氰酸根合丙基）酰胺。除了几个例子外，一些吡啶鎓（不对称取代的氰基甲基化物）与乙炔二甲酸二甲酯 (DMAD) 在各种溶剂中的 1,3-偶极环加成仅得到 3-氰基吲哚腙-1,2-二甲酸二甲酯。另一方面，用强碱（如叔丁醇钾）处理吡啶鎓（硫氰基乙酰基）-或（2-硫氰基丙酸基）酰胺，得到了新的双环介离子化合物 N-[2-(1,3,4-噻二唑并[3,2-a]吡啶并)]乙酰胺衍生物，收率适中。N-[1-(2-thiocyanatopyridinio)]aceta的中间体...
• Spectrophotometric Studies of Reactions of the Aquapentacyanoferrate(II) Ion with Ketones. Kinetics and Mechanism of the Substitution Reaction of the Aquapentacyanoferrate(II) Ion with 1-Benzoylethylpyridinium Chloride
  作者：Jasna Lovrić、Blaženka Foretić、Nicoletta Burger

  DOI：10.1524/zpch.218.11.1289.50813

  日期：2004.11.1

  The carbonyl group of compounds of the phenacyl- and benzoylethyl-pyridinium type is recognized as a potential σ donor ligand which can produce complexes with the aquapentacyanoferrate(II) ion. Its reactive form is the ionized one i.e. the enolate ion. A detailed spectrophotometric investigation has been made for the reaction of the aquapentacyanoferrate(II) ion with 1-benzoylethylpyridinium chloride. The equilibrium constant of the produced complex was derived using two literatury available additional types of processing the molar ratio method’s experimental data which were not found to be applied to this type of complexes. The kinetics of this substitution reaction were studied in buffered solutions at pH = 8.0 and I = 0.05 M. The obtained results are consistent with a dissociative mechanism.

  苯乙酰基和苯甲酰乙基吡啶类化合物的羰基基团被认为是一种潜在的σ供体配体，可以与五氰合铁(II)离子形成配合物。它的反应形式是离子化的烯醇离子。对五氰合铁(II)离子与1-苯甲酰乙基吡啶盐酸盐反应进行了详细的光谱学研究。利用两种文献上可得到的附加型的摩尔比法实验数据处理方法，得出了所产生的配合物的平衡常数，这些方法并未被应用于这类配合物。在pH=8.0和I=0.05 M的缓冲溶液中研究了这种取代反应的动力学。所得结果与解离机理一致。

• Oral hypoglycemic agents. Discovery and structure-activity relationships of phenacylimidazolium halides
  作者：Samuel J. Dominianni、Terence T. Yen

  DOI：10.1021/jm00130a013

  日期：1989.10

  Blood glucose levels in viable, yellow, obese, diabetic mice are reduced following oral administration of phenacylimidazolium halides. Compounds 2 and 3 produced reductions of ca. 40% 2 h after doses of 100 mg/kg po. Since these mice do not respond to sulfonylureas, the glucose-lowering activity of phenacylimidazolium salts in this model suggests a mechanism other than that of stimulating insulin secretion. Only phenacylimidazolium halides with electron-donating groups were active; other azolium salts or variations in the phenacyl portion (alterations in the keto function; chain lengthening or extensive branching) produced inactive compounds.
• Synthesis and biological evaluation of a new series of phenothiazine-containing protein farnesyltransferase inhibitors
  作者：Cristina-Maria Abuhaie、Alina Ghinet、Amaury Farce、Joëlle Dubois、Philippe Gautret、Benoît Rigo、Dalila Belei、Elena Bîcu

  DOI：10.1016/j.ejmech.2012.11.008

  日期：2013.1

  Two new families of human farnesyltransferase inhibitors 13a-m and 14a-d, based on a phenothiazine scaffold, were synthesized. Compounds 14a and 14b were the most promising inhibitors of human farnesyltransferase with IC50 values of 0.7 and 0.6 mu M, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.