2,6-bis(4-ethoxyphenyl)pyridine | 21172-82-7

• 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: 2,6-bis(4-ethoxyphenyl)pyridine
• CAS: 21172-82-7
• 化学式: C₂₁H₂₁NO₂
• mdl: MFCD00626029
• 分子量: 319.403
• InChiKey: ALCGVZXVYKUILM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二氯吡啶 、 三对乙氧基苯基铋 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以78%的产率得到2,6-bis(4-ethoxyphenyl)pyridine
  参考文献：
  名称：

  Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis

  摘要：

  This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines in high yields. The couplings addressed with dihalopyridines have afforded chemo- and regio-selective coupling products. Arylations of 2-chloroquinoline with different triarylbismuth reagents demonstrated fruitful coupling reactivity under the established conditions. This sumptuous study demonstrates the remarkable cross-coupling reactivity of iodo/chloropyridines and chloroquinoline with triarylbismuth reagents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.036

文献信息

• Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1002/ejoc.201402455

  日期：2014.8

  Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot

  公开了在 Pd 催化条件下使用溴吡啶和溴喹啉与三芳基铋作为亚化学计量量的三重偶联试剂的交叉偶联研究。与单-和二溴吡啶基底物的反应性很高，并且单-和双-偶联是区域选择性地进行的。以高产率形成了单芳基和二芳基吡啶库。一锅法提供了对称和不对称二芳基吡啶的简单直接合成。使用三芳基铋试剂实现了 2-溴和 3-溴喹啉的芳基化。该研究表明，三芳基铋可用作三重芳基化试剂，用于在 Pd 催化条件下通过与溴吡啶和溴喹啉偶联合成芳基吡啶和喹啉。
• Pd-Catalyzed Decarboxylation and Dual C(sp³)–H Functionalization Protocols for the Synthesis of 2,4-Diarylpyridines
  作者：Raghuram Gujjarappa、Nagaraju Vodnala、Mohan Kumar、Chandi C. Malakar

  DOI：10.1021/acs.joc.8b02971

  日期：2019.5.3

  The Pd-catalyzed decarboxylation and dual C(sp3)–H bond functionalization approaches have been described for the preparation of symmetrical and unsymmetrical 2,4-diarylpyridines. The developed transformations were realized using nonactivated aromatic ketones and amino acids as C–N sources. The efficacy of the catalyst and reagent combination drives the transformation toward the formation of desired

  Pd催化的脱羧作用和双重C（sp 3）–H键官能化方法已被描述用于制备对称和不对称的2,4-二芳基吡啶。使用非活化的芳族酮和氨基酸作为C–N来源可以实现发达的转化。催化剂和试剂组合的功效推动了向高产率和高选择性的所需产物形成的转化。所描述的反应条件通过[2 + 2 + 2]环加成诱导了苯丙氨酸的自反应，并最小化了3,5-苯基吡啶作为副产物的形成，而使用甘氨酸作为C–N来源，相应的2， 6-二芳基吡啶是次要产物。
• Selective Suzuki-Miyaura Monocouplings with Symmetrical Dibromoarenes and Aryl Ditriflates for the One-Pot Synthesis of Unsymmetrical Triaryls
  作者：Corinne Minard、Carole Palacio、Kevin Cariou、Robert H. Dodd

  DOI：10.1002/ejoc.201400090

  日期：2014.5

  parameters that would permit selective Suzuki–Miyaura monocouplings of symmetrical dihaloarenes were studied. High selectivity and efficiency can be obtained for a broad range of substrates by using operationally simple conditions and widely available reagents. The 38 different examples described provide a valuable toolbox for the rapid access to unsymmetrical triaryls, as illustrated by the preparation

  研究了允许对称二卤芳烃选择性 Suzuki-Miyaura 单偶联的各种参数。通过使用操作简单的条件和广泛可用的试剂，可以获得对广泛底物的高选择性和效率。所描述的 38 个不同的例子为快速获取不对称三芳基提供了一个有价值的工具箱，如二芳基吡啶 8、三联苯 9 和二芳基吡咯 10 的制备所示。
• PROCESS FOR PRODUCTION OF DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALYST, PROCESS FOR PRODUCTION OF -AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE SALT
  申请人：National University Corporation Nagoya University

  公开号：EP2208722A1

  公开（公告）日：2010-07-21

  Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1'-binaphthyl-2,2'-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80°C for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1'-binaphthyl-2,2'-disulfonate. The (R)-1,1'-binaphthyl-2,2'-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH2Cl2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0°C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0°C for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.

  在装有 (R)-1,1'-联萘-2,2'-二硫醇和氢氧化钾的反应容器中加入六甲基磷酰胺（HMPA）。在 7 个大气压的氧气条件下，用氧气吹扫该容器并在 80°C 下搅拌 5 天。冷却至室温后，纯化反应产物，得到(R)-1,1'-联萘-2,2'-二磺酸钾。将从二磺酸盐中得到的 (R)-1,1'-联萘-2,2'-二磺酸和 2,6-二苯基吡啶在乙腈中搅拌，然后减压蒸发溶剂。随后，向反应产物中加入硫酸镁和蒸馏过的 CH2Cl2，并在室温下搅拌混合物 30 分钟。所得溶液冷却至 0°C。在 1 小时内向溶液中滴入氮被 Cbz 保护的苯甲醛亚胺，随后滴入乙酰丙酮。所得混合物在 0°C 下继续搅拌 30 分钟。由此制得相应的 β-氨基羰基衍生物，收率为 91%，对映体过量率为 90%ee。
• PROCESS FOR MANUFACTURING DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALST, PROCESS FOR MANUFACTURING BETA-AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE
  申请人：Ishihara Kazuaki

  公开号：US20100249431A1

  公开（公告）日：2010-09-30

  Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1′-binaphthyl-2,2′-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80° C. for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1′-binaphthyl-2,2′-disulfonate. The (R)-1,1′-binaphthyl-2,2′-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH 2 Cl 2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0° C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0° C. for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.