methyl 2-methyl-6-phenyl-3-pyridinecarboxylate | 66416-48-6

• 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: methyl 2-methyl-6-phenyl-3-pyridinecarboxylate
• 英文别名: methyl 2-methyl-6-phenylpyridine-3-carboxylate；methyl 2-methyl-6-phenylnicotinate；2-methyl-6-phenyl-nicotinic acid methyl ester；2-Methyl-3-carbomethoxy-6-phenyl-pyridin
• CAS: 66416-48-6
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: HHVSDTJQFIOFEY-UHFFFAOYSA-N

物化性质

• 沸点：
  326.1±30.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-6-phenyl-3-pyridinecarboxylate 在 selenium(IV) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 15.0h， 以45%的产率得到2-Formyl-6-phenyl-nicotinic acid methyl ester
  参考文献：
  名称：

  Graef, Edgar; Troschuetz, Reinhard, Synthesis, 1999, # 7, p. 1216 - 1222

  摘要：

  DOI：
• 作为产物：
  描述：

  6-羟基-2-甲基吡啶-3-羧酸 在 四(三苯基膦)钯 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 、 乙酰氯 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 144.0h， 生成 methyl 2-methyl-6-phenyl-3-pyridinecarboxylate
  参考文献：
  名称：

  Biaryl substituted alkylboronate esters as thrombin inhibitors

  摘要：

  Thrombin is a serine protease that plays an important role in the blood coagulation cascade, and is a target enzyme for new therapeutic agents. Ac-(D)-Phe-Pro-boroArg-OH (DuP714) was found to be a highly effective thrombin inhibitor. In order to reduce the peptidic nature of DuP 714, we have designed a series of novel biaryl substituted alkylboronate esters as potent thrombin inhibitors. The most potent compounds have subnanomolar affinity for thrombin. (C) 1997 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00254-0

文献信息

• Tailor-made synthesis of fully alkylated/arylated nicotinates by FeCl₃-mediated condensation of enamino esters with enones
  作者：Sho Hirai、Yurie Horikawa、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1039/c7cc00051k

  日期：——

  A new method for synthesizing polyalkylated/arylated nicotinates is established using a condensation of enamino esters with enones in the presence of FeCl3. This method facilitates the introduction of alkyl or...

  在FeCl3存在下，使用烯胺酯与烯酮的缩合，建立了一种合成多烷基化/芳基烟酸酯的新方法。这种方法有助于引入烷基或...
• Ionic liquid promoted simple and efficient synthesis of β-enamino esters and β-enaminones from 1,3-dicarbonyl compounds – One-pot, three-component reaction for the synthesis of substituted pyridines
  作者：Ganesan Karthikeyan、Paramasivan T Perumal

  DOI：10.1139/v05-186

  日期：2005.10.1

  A facile enamination of 1,3-dicarbonyl compounds with amines has been developed that affords good to excellent yields of β-enamino esters and β-enaminones using Brønsted acidic ionic liquid 1-methylimidazolium trifluoroacetate ([Hmim]⁺Tfa^–) at room temperature. This methodology has been extended for the synthesis of substituted pyridines in excellent yield by a one-pot, three-component reaction of 1,3-dicarbonyl compounds, ammonium acetate, and alkynone in the presence of [Hmim]⁺Tfa^–.Key words: ionic liquid, β-enaminones, β-enamino esters, 1,3-dicarbonyl compounds, amines, pyridines.

  已开发出一种简便的方法，利用Brønsted酸性离子液体1-甲基咪唑三氟乙酸盐([Hmim]⁺Tfa^–)在室温下与胺类化合物进行1,3-二羰基化合物的反应，得到良好至优异产率的β-烯胺酯和β-烯酮。该方法已扩展到通过在[Hmim]⁺Tfa^–存在下进行1,3-二羰基化合物、醋酸铵和炔酮的一锅法三组分反应，以优异产率合成取代吡啶。关键词：离子液体，β-烯酮，β-烯胺酯，1,3-二羰基化合物，胺类，吡啶。
• A Concise Route to Pyridines from Hydrazides by Metal Carbene N−H Insertion, 1,2,4-Triazine Formation, and Diels−Alder Reaction
  作者：Baolu Shi、William Lewis、Ian B. Campbell、Christopher J. Moody

  DOI：10.1021/ol901502u

  日期：2009.8.20

  three-step sequence for the conversion of hydrazides into pyridines is reported in which the key steps are N−H insertion by a copper carbene intermediate derived from α-diazo-β-ketoesters into the hydrazide, reaction with ammonium acetate to give 1,2,4-triazines, followed by Diels−Alder reaction with norbornadiene.

  据报道，酰肼转化为吡啶的简单，新的三步过程，其中关键步骤是将衍生自α-重氮-β-酮酸酯的铜卡宾中间体将N-H插入酰肼中，并与乙酸铵反应生成氨。得到1,2,4-三嗪，然后与降冰片二烯进行狄尔斯-阿尔德反应。
• Reaction of <i>N</i>-Vinylic Phosphazenes with α,β-Unsaturated Aldehydes. Azatriene-Mediated Synthesis of Dihydropyridines and Pyridines Derived from β-Amino Acids
  作者：Francisco Palacios、Esther Herrán、Concepción Alonso、Gloria Rubiales、Begoña Lecea、Mirari Ayerbe、Fernando P. Cossío

  DOI：10.1021/jo060775b

  日期：2006.8.1

  Aza-Wittig reaction of N-vinylic phosphazenes (1,2 addition), derived from diphenylmethylphosphine or derived from trimethylphosphine with α,β-unsaturated aldehydes, leads to the formation of 3-azatrienes through a [2 + 2]-cycloaddition−cycloreversion sequence. The presence of an alkyl substituent in position 3 of N-vinylic phosphazenes increases the steric interactions, and [4 + 2] periselectivity

  衍生自二苯基甲基膦或衍生自三甲基膦的N-乙烯基磷腈的Aza-Wittig反应（1,2加成）与α，β-不饱和醛反应，通过[2 + 2]-环加成-环还原反应生成3-氮杂烯顺序。N-乙烯基磷腈的3位上存在烷基取代基会增加空间相互作用，并且观察到[4 + 2]的选择性（1,4加成）。氮杂三烯与α，β-不饱和醛的反应产生吡啶。
• Domino synthesis of functionalized pyridine carboxylates under gallium catalysis: Unravelling the reaction pathway and the role of the nitrogen source counter anion
  作者：Dinesh Kumar、Himanshu Sharma、Nirjhar Saha、Asit K. Chakraborti

  DOI：10.1002/asia.202200304

  日期：2022.8

  domino Michael-cyclodehydration-aromatization multicomponent reaction for the synthesis of functionalized pyridines from enaminones, 1,3-diketones, and NH4OAc under solvent-free condition is reported. The method is simple, high-yielding, and operates under mild conditions with a wide substrate scope. The use of different ammonium salts as a nitrogen source was investigated and the decisive role of the acetate

  报道了在无溶剂条件下由烯胺酮、1,3-二酮和 NH 4 OAc 合成官能化吡啶的 GaI 3催化多米诺迈克尔环脱水芳构化多组分反应。该方法简单、收率高、操作条件温和、底物范围广。研究了使用不同的铵盐作为氮源，并确定了醋酸盐抗衡阴离子的决定性作用。