2,2',6,6'-tetramethoxy-3,3'-bipyridine | 214360-53-9

• 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: 2,2',6,6'-tetramethoxy-3,3'-bipyridine
• 英文别名: 3-(2,6-Dimethoxypyridin-3-yl)-2,6-dimethoxypyridine
• CAS: 214360-53-9
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: BVNDJMRXHKGPKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,6-二甲氧基吡啶 在 1,10-菲罗啉 、 palladium diacetate 、 potassium carbonate 、 silver carbonate 作用下， 反应 48.0h， 生成 2,2',6,6'-tetramethoxy-3,3'-bipyridine
  参考文献：
  名称：

  Pd（II）催化（杂）芳烃进行吡啶的C3选择性芳基化

  摘要：

  在1,10-菲咯啉作为配体的情况下，开发了钯与芳烃和杂芳烃催化的C3选择性非定向芳构化芳基化合物。优化的条件允许吡啶的高度C3选择性芳基化，提供各种3,3'-联吡啶和3-芳基吡啶。

  DOI：

  10.1021/acs.orglett.5b03712

文献信息

• [EN] PROCESS FOR THE PREPARATION OF CHIRAL AMINES BY ASYMMETRIC HYDROGENATION OF PROCHIRAL OXIMES<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMINES CHIRALES PAR HYDROGÉNATION ASYMÉTRIQUE D'OXIMES PROCHIRAUX
  申请人：SP PROCESS DEV AB

  公开号：WO2015178847A1

  公开（公告）日：2015-11-26

  There is provided a method for the preparation of an enantiomerically enriched amine by asymmetric hydrogenation of a prochiral oxime.

  提供了一种通过对一个非手性亚硝酮进行不对称氢化来制备对映体富集胺的方法。
• [EN] PROCESS FOR THE PREPARATION OF CHIRAL AMINES FROM PROCHIRAL KETONES<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMINES CHIRALES À PARTIR DE CÉTONES PROCHIRALES
  申请人：SP PROCESS DEV AB

  公开号：WO2015178846A1

  公开（公告）日：2015-11-26

  There is provided a method for the preparation of an enantiomerically enriched amine from a prochiral ketone.

  提供了一种从原构手性酮制备手性富集胺的方法。
• Deprotonative metalation of substituted aromatics using mixed lithium–cobalt combinations
  作者：Gandrath Dayaker、Floris Chevallier、Philippe C. Gros、Florence Mongin

  DOI：10.1016/j.tet.2010.09.053

  日期：2010.11

  The deprotonation of anisole was attempted using different homo- and heteroleptic TMP/Bu mixed lithium–cobalt combinations. Using iodine to intercept the metalated anisole, an optimization of the reaction conditions showed that in THF at room temperature 2 equiv of base were required to suppress the formation of the corresponding 2,2′-dimer. The origin of the dimer was not identified, but its formation

  苯甲醚的去质子化尝试使用不同的均配和杂配的TMP / Bu混合锂钴混合物。使用碘截留金属化的茴香醚，反应条件的优化表明，在室温下的THF中，需要2当量的碱才能抑制相应的2,2'-二聚体的形成。二聚体的来源尚未确定，但烯丙基溴作为亲电子试剂有利于其形成。使用碘，茴香醛和氯二苯膦有效地捕集金属化的苯甲醚，并适当使用二苯甲酮和苯甲酰氯。类似地将1，2-，1，3-和1，4-二甲氧基苯区域选择性地转化为相应的碘化物。观察到2-甲氧基-和2，当进行类似处理时，6-二甲氧基吡啶比相应的苯更易于二聚。苯甲酸乙酯在金属化-碘化过程中的参与表明，该方法不适用于对具有反应性功能的底物进行功能化。
• Process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：US11053188B2

  公开（公告）日：2021-07-06

  The present invention relates to a process for the preparation of enantiomerically and diastereomerically enriched cyclobutane amines and amides by reacting (a) cyclopropylcarbonitrile to a cyclopropylcarbaldehyde, (b) further reacting to a cyclobutanone, or (d′) further reacting to an enamide, (c) further reacting to enantiomerically and diastereomerically enriched cyclobutane amines, or (d) further reacting to an enamide and (e) to an enantiomerically and diastereomerically enriched cyclobutylamide to obtain (f) an enantiomerically and diastereomerically enriched cyclobutane amine, and (g) further reacting to an enantiomerically and diastereomerically enriched cyclobutane amide.

  本发明涉及一种制备对映体和非对映异构体富集的环丁烷胺和酰胺的工艺，该工艺通过(a)环丙基甲腈与环丙基甲醛反应，(b)进一步与环丁酮反应，或(d′)进一步与烯酰胺反应，(c)进一步与对映体和非对映异构体富集的环丁烷胺反应、或(d)与烯酰胺和(e)与对映体和非对映异构体富集的环丁基酰胺进一步反应，得到(f)对映体和非对映异构体富集的环丁烷胺，和(g)与对映体和非对映异构体富集的环丁烷酰胺进一步反应。
• Deprotonative metalation of aromatic compounds using mixed lithium–iron combinations
  作者：Elisabeth Nagaradja、Floris Chevallier、Thierry Roisnel、Viatcheslav Jouikov、Florence Mongin

  DOI：10.1016/j.tet.2012.02.019

  日期：2012.4

  The deprotonation of 2-methoxypyridine was attempted using putative (TMP)(3)FeLi prepared from different iron sources. Using iodine to intercept the metalated 2-methoxypyridine, the best result was obtained from FeBr2 (1 equiv) using THF at room temperature: nevertheless, in addition to the expected iodide, the corresponding 2,2'-dimer was obtained (86% total yield). The origin of the competitive formation of the 2,2'-dimer was not identified but mechanisms were suggested to explain its formation. It was observed that the nature of the electrophile employed to trap the 3-metalated 2-methoxypyridine has a strong impact on this dimer formation, the latter being favored using iodine (35% yield), but also benzophenone (28%), benzoyl chloride (22%), methyl iodide (27%), allyl bromide (15%), benzyl bromide (41%), and tetramethylthiuram disulphide (36%); for this reason, the yields of the expected derivatives were only 51, 15, 62, 0, <5, 18, and 0%, respectively. In contrast, using aldehydes readily led to the expected pyridine alcohols without dimerization (59% yield using 3,4,5-trimethoxybenzaldehyde and 66% yield using pivalaldehyde). 2,6-Dimethoxypyridine (in 68% yield), anisole (47%), 2,4-dimethoxypyrimidine (50% at C5 and 3% at C6), 2-fluoropyridine (64%), and thiophene (49%) were similarly converted into the corresponding alcohols after subsequent trapping with pivalaldehyde. Using iodine to trap the 2-metalated anisole did not lead to dimer formation, and 2-iodoanisole was isolated in 71% yield. (C) 2012 Elsevier Ltd. All rights reserved.