2-[2-(4-methoxyphenyl)ethyl]pyridine | 46739-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[2-(4-methoxyphenyl)ethyl]pyridine
• 英文别名: 2-(4-methoxyphenethyl)pyridine；2-(4-methoxy-phenethyl)-pyridine；2-(4-Methoxy-phenaethyl)-pyridin；1-Anisyl-2-β-pyridylethanol
• CAS: 46739-62-2
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: ACZSUOYUNBXYLN-UHFFFAOYSA-N

物化性质

• 沸点：
  183-184 °C(Press: 11 Torr)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-(4-methoxyphenyl)ethyl]pyridine 在 氨 、 potassium amide 作用下， 生成 [4-(4-methoxy-phenyl)-3-[2]pyridyl-butyl]-dimethyl-amine
  参考文献：
  名称：

  Histamine Antagonists. γ,γ-Disubstituted N,N-Dialkylpropylamines¹

  摘要：

  DOI：

  10.1021/ja01156a078
• 作为产物：
  描述：

  diethyl 2-(4-methoxybenzyl)-2-(pyridin-2-yl)malonate 在 柠檬酸 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 2-[2-(4-methoxyphenyl)ethyl]pyridine
  参考文献：
  名称：

  An efficient synthesis of 2-alkylpyridines using an alkylation/double decarboxylation strategy

  摘要：

  We have discovered a novel route for synthesising 2-alkylpyridines by exploiting the decarboxylation of pyridyl malonate esters. Herein we report the synthesis of a number of examples and describe how the reaction was discovered. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.049

文献信息

• New studies of Rh-catalyzed addition of boronic acids under basic conditions in aqueous medium
  作者：Rémi Amengual、Véronique Michelet、Jean-Pierre Genêt

  DOI：10.1016/s0040-4039(02)01274-1

  日期：2002.8

  efficiently performed. The addition of various boronic acids to styrene, 2-vinylpyridine, and cyclic α,β-unsaturated ketones has been realized with high selectivity and yield. We have shown that m-TPPTC (tris(m-carboxyphenyl)phosphane trilithium salt) exhibited a higher reactivity compared to TPPTS. These couplings could also be conducted very efficiently under basic and phosphaneless conditions to give

  在碱性条件下，在纯净水中有效地进行了Rh催化的C formationC键的形成。已经以高选择性和高产率实现了向苯乙烯，2-乙烯基吡啶和环状α，β-不饱和酮中添加各种硼酸。我们已经表明，米-TPPTC（三（米相比TPPTS -carboxyphenyl）膦三锂盐）表现出更高的反应性。这些偶联也可以在碱性和无膦条件下非常有效地进行，以得到官能化的芳基衍生物。附加的阴离子配体m -TPPTC的好处在于成功进行了1,4-苯硼酸加成至环己烯酮的循环实验，而不会损失水溶性催化剂。
• Construction of α-Amino Azines via Thianthrenation-Enabled Photocatalyzed Hydroarylation of Azine-Substituted Enamides with Arenes
  作者：Yu-Lan Zhang、Gang-Hu Wang、Yichen Wu、Chun-Yin Zhu、Peng Wang

  DOI：10.1021/acs.orglett.1c03229

  日期：2021.11.5

  Herein, we report a practical method for accessing this class of compounds via photocatalyzed hydroarylation of azine-substituted enamides with the in situ-generated aryl thianthrenium salts as the radical precursor. This reaction features a broad substrate scope, good functional group tolerance, and mild conditions and is suitable for the late-stage installation of α-amino azines in complex structures

  α-氨基吖嗪广泛存在于药物和配体中。在此，我们报告了一种实用的方法，该方法通过以原位生成的芳基硫鎓盐作为自由基前体，对吖嗪取代的烯酰胺进行光催化加氢芳基化来获得这类化合物。该反应具有底物范围广、官能团耐受性好、条件温和等特点，适用于复杂结构中α-氨基吖嗪的后期安装。
• Pd–NHC (NHC = N-Heterocyclic Carbene)-Catalyzed B-Alkyl Suzuki Cross-Coupling of 2-Pyridyl Ammonium Salts by N–C Activation: Application to the Discovery of Agrochemical Molecular Hybrids
  作者：Yanqing Gao、Yuge Hu、Jiuhui Ye、Zhiqing Ma、Juntao Feng、Xili Liu、Peng Lei、Michal Szostak

  DOI：10.1021/acs.orglett.4c00549

  日期：2024.3.22

  natural products, pharmaceuticals, and agrochemicals. Herein, we report the first B-alkyl Suzuki cross-coupling of 2-pyridyl ammonium salts to access functionalized 2-alkylpyridines. The use of well-defined, operationally simple Pd-NHCs permits for an exceptionally broad scope of the challenging B-alkyl C–N cross-coupling with organoboranes containing β-hydrogen, representing a novel method for the discovery

  2-烷基吡啶是整个有机合成领域的一种特殊支架，在天然产物、药物和农用化学品中发挥着关键作用。在此，我们报道了 2-吡啶基铵盐的第一个 B-烷基 Suzuki 交叉偶联以获得功能化的 2-烷基吡啶。使用结构明确、操作简单的 Pd-NHC 可以实现极其广泛的具有挑战性的 B-烷基 C-N 与含有 β-氢的有机硼烷的交叉偶联，代表了一种发现备受追捧的分子的新方法用于植物保护。
• Ligand-Enabled Palladium(II)-Catalyzed γ-C(sp³)–H Arylation of Primary Aliphatic Amines
  作者：Chen-Hui Yuan、Lei Jiao

  DOI：10.1021/acs.orglett.3c03186

  日期：2024.1.12

  The Pd(II)/sulfoxide-2-hydroxypyridine catalytic system shows promising activity in C–H activation chemistry. In this study, we showcase how this catalytic system solves the problem of native primary amine-directed γ-C(sp3)–H arylation. Primary amines with different complexities are compatible with the established methodology, and the range of applicable substrates can be expanded to include pyridine

  Pd(II)/亚砜-2-羟基吡啶催化体系在 C-H 活化化学中表现出良好的活性。在这项研究中，我们展示了该催化系统如何解决天然伯胺导向的 γ-C(sp 3 )–H 芳基化问题。不同复杂度的伯胺与已建立的方法兼容，并且适用的底物范围可以扩大到包括吡啶、肟醚和吡啶N-氧化物。
• Catalytic Alkylation of Methyl-<i>N</i>-Heteroaromatics with Alcohols
  作者：Benoît Blank、Rhett Kempe

  DOI：10.1021/ja9095413

  日期：2010.1.27

  A novel Catalytic C-C coupling reaction in which N-heteroaromatic-substituted methyl groups are efficiently alkylated using, primary alcohols is introduced. The synthesis protocol is based on iridium catalysts and most likely relies on the "borrowing hydrogen" or "hydrogen autotransfer" mechanism. A variety Of substrate combinations can readily be employed in this reaction, including pyrimidines, pyridazines, and even fairly activated 2- and 4-picolines.