ethyl 2-methyl-4-phenylnicotinate | 61209-74-3

• 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: ethyl 2-methyl-4-phenylnicotinate
• 英文别名: ethyl 2-methyl-4-phenylpyridine-3-carboxylate
• CAS: 61209-74-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: JHGQBYHIUKINFR-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±30.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-4-phenylnicotinate 在 氯化亚砜 、 一水合肼 、 三乙胺 、 间氯过氧苯甲酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 45.0h， 生成 N-[3,5-bis(trifluoromethyl)benzyl]-5-methyl-7-phenyl-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide
  参考文献：
  名称：

  Non-peptide NK1 receptor ligands based on the 4-phenylpyridine moiety

  摘要：

  The quinoline nucleus of the previously described 4-phenylquinoline-3-carboxamides NK1 receptor ligands 7 has been transformed into either substituted or azole-(i.e., triazole or tetrazole) fused pyridine moieties of compounds 9 and 10, respectively, in order to obtain NK1 receptor ligands showing lower molecular weight or higher hydrophilicity. The program of molecular manipulations produced NK1 receptor ligands showing affinity in the nanomolar range. In particular, 4-methyl-1-piperazinyl derivative 9j showed an IC50 value of 4.8 nM and was proved to behave as a NK1 antagonist blocking Sar(9)-SP-sulfone induced proliferation and migration of microvascular endothelial cells. Therefore, compound 9j has been labeled with [C-11]CH3I (t(1/2) = 20.4 min, beta(+) = 99.8%) starting from the corresponding des-methyl precursor 9i using with a radiochemical yield of about 10% (not decay corrected) and a specific radioactivity > 1 Ci/mu mol in order to be used as a radiotracer in next PET studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.031
• 作为产物：
  描述：

  2-甲基-4-苯基-1,4-二氢吡啶-3-羧酸乙酯 在 硫化氢 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 ethyl 2-methyl-4-phenylnicotinate
  参考文献：
  名称：

  6-(((Substituted)pyridin-3-yl)alkyl)-and

  摘要：

  某些转化的trans-6-[[(取代的)吡啶-3-基]-烷基和烯基]四氢-4-羟基吡喃-2-酮及其相应的开环酸是酶3-羟基-3-甲基戊二酰辅酶A还原酶（HMG-CoA还原酶）的有效抑制剂，并可用作降胆固醇和降脂药物。

  公开号：

  US04906624A1

文献信息

• Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant
  作者：Jordan D. Galloway、Duy N. Mai、Ryan D. Baxter

  DOI：10.1021/acs.orglett.7b02706

  日期：2017.11.3

  A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C–H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.

  报道了一种使用Selectfluor作为温和氧化剂进行银催化Minisci反应的新方法。杂芳烃和醌都参与各种羧酸和硼酸自由基前体的C–H自由基烷基化和芳基化。几种具有氧化敏感性和高反应性的自由基物种非常成功，它们提供了难以通过其他方式接近的结构。
• One-Pot Reactions for Modular Synthesis of Polysubstituted and Fused Pyridines
  作者：Zhidong Song、Xin Huang、Wenbin Yi、Wei Zhang

  DOI：10.1021/acs.orglett.6b02883

  日期：2016.11.4

  3-dicarbonyl-initiated one-pot Michael addition/[5 + 1] annulation/dehydrofluorinative aromatization reaction sequence is introduced for regioselective synthesis of di-, tri-, tetra-, and pentasubstituted pyridines as well as fused pyridines. This simple and modular synthesis is performed using readily available starting materials and under transition-metal catalyst-free conditions.

  引入2-氟-1,3-二羰基引发的一锅迈克尔加成反应/ [5 +1]环化/脱氟化氢芳构化反应顺序，用于区域选择性合成二，三，四和五取代的吡啶以及吡啶。使用容易获得的原料并在无过渡金属的条件下进行这种简单而模块化的合成。
• Substrate Control in the Gold(I)-Catalyzed Cyclization of β<i>-</i>Propargylamino Acrylic Esters and Further Transformations of the Resultant Dihydropyridines
  作者：Jiří Mikušek、Petr Matouš、Eliška Matoušová、Martin Janoušek、Jiří Kuneš、Milan Pour

  DOI：10.1002/adsc.201600412

  日期：2016.9.15

  β‐propargylamino acrylic esters with a push‐pull olefinic bond afforded good to high yields of dihydropyridines upon treatment with 5% tris(2‐furyl)phosphine‐gold(I) chloride/silver(I) tetrafluoroborate [(TFP)AuCl/AgBF4] in anhydrous benzene. Carbamate and sulfonyl groups were employed for nitrogen protection. On a model enyne, the p‐methoxybenzenesulfonyl (MBS) group was found to be a better protective

  N-保护的带有推挽式烯烃键的β-炔丙基氨基丙烯酸酯，在用5％的三（2-呋喃基）膦-氯化金（I）/四氟硼酸银（I）处理后，可提供高至高产率的二氢吡啶。在无水苯中的AuCl / AgBF 4 ]。氨基甲酸酯和磺酰基用于氮保护。在模型恩尼（Enyne）上，p就环化收率以及消除相应2,3,4-三取代吡啶的收率而言，发现甲氧基苯磺酰基（MBS）基比甲苯磺酰基更好。Boc保护的二氢吡啶在环化条件下进行了部分脱保护/氧化，这使得相应吡啶的更直接，一锅法制备成为可能。在另一个应用中，将被保护为稳定的甲氧基氨基甲酸酯的适当取代的衍生物进行催化氢化，得到已知的帕罗西汀前体。烯炔环化的化学选择性（二氢吡啶与。吡咯）除其他因素外，还受C-3取代的支配。当C-3未取代时，无论催化剂/条件如何，均以二氢吡啶为唯一产物。
• A heavy metal- and oxidant-free, one-pot synthesis of pyridines and fused pyridines based on a Lewis acid-catalyzed multicomponent reaction
  作者：V. P. Alex Raja、Giammarco Tenti、Subbu Perumal、J. Carlos Menéndez

  DOI：10.1039/c4cc01791a

  日期：——

  The InCl3-catalyzed sequential multicomponent reaction between 2-furfurylamine, β-dicarbonyl compounds and α,β-unsaturated aldehydes in ethanol, followed by microwave irradiation in solvent-free conditions, afforded good to excellent yields of highly substituted pyridines, with loss of a 2-furylmethyl side chain. The method was also adapted to the synthesis of quinolones, isoquinolines, phenanthridines

  乙醇中2-糠胺，β-二羰基化合物与α，β-不饱和醛之间的InCl3催化顺序多组分反应，然后在无溶剂条件下进行微波辐照，可得到高至优收率的高度取代的吡啶，且不损失2-呋喃甲基侧链。该方法还适用于喹诺酮，异喹啉，菲啶和更复杂的稠合吡啶体系的合成。
• 6-(((substituted)pyridin-3-yl)alkyl)-and
  申请人：Warner-Lambert Company

  公开号：US04997837A1

  公开（公告）日：1991-03-05

  Certain trans-6-[[(substituted)pyridin-3-yl]-alkyl- and alkenyl]tetrahydro-4-hydroxypyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.

  某些取代的吡啶-3-基-烷基和烯基四氢-4-羟基吡喃-2-酮及其对应的开环酸衍生物是酶3-羟基-3-甲基戊二酰辅酶A还原酶（HMG-CoA还原酶）的有效抑制剂，可用作降低胆固醇和血脂的药物。