2,6-diheptylpyridine

• 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-diheptylpyridine
• 化学式: C₁₉H₃₃N
• 分子量: 275.478
• InChiKey: KNFUXSRLRRWZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-diheptylpyridine 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 以86%的产率得到2,6-diheptyl-1-methylpyridinium trifluoromethanesulfonate
  参考文献：
  名称：

  Structure–Affinity Relationships (SARs) and Structure–Kinetics Relationships (SKRs) of K_v11.1 Blockers

  摘要：

  K(v)11.1 (hERG) blockers with comparable potencies but different binding kinetics might display divergent proarrhythmic risks. In the present study, we explored structure-kinetics relationships in four series of K(v)11.1 blockers next to their structure affinity relationships. We learned that despite dramatic differences in affinities and association rates, there were hardly any variations in the dissociation rate constants of these molecules with residence times (RTs) of a few minutes only. Hence, we synthesized 16 novel molecules, in particular in the pyridinium class of compounds, to further address this peculiar phenomenon. We found molecules with very short RTs (e.g., 0.34 min for 37) and much longer RTs (e.g., 105 min for 38). This enabled us to construct a k(on)-k(off)-K-D kinetic map for all compounds and subsequently divide the map into four provisional quadrants, providing a possible framework for a further and more precise categorization of K(v)11.1 blockers. Additionally, two representative compounds (21 and 38) were tested in patch clamp assays, and their RTs were linked to their functional IC50 values. Our findings strongly suggest the importance of the simultaneous study of ligand affinities and kinetic parameters, which may help to explain and predict K(v)11.1-mediated cardiotoxicity.

  DOI：

  10.1021/acs.jmedchem.5b00518
• 作为产物：
  描述：

  2,6-di(hept-1-ynyl)pyridine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以43%的产率得到2,6-diheptylpyridine
  参考文献：
  名称：

  Structure–Affinity Relationships (SARs) and Structure–Kinetics Relationships (SKRs) of K_v11.1 Blockers

  摘要：

  K(v)11.1 (hERG) blockers with comparable potencies but different binding kinetics might display divergent proarrhythmic risks. In the present study, we explored structure-kinetics relationships in four series of K(v)11.1 blockers next to their structure affinity relationships. We learned that despite dramatic differences in affinities and association rates, there were hardly any variations in the dissociation rate constants of these molecules with residence times (RTs) of a few minutes only. Hence, we synthesized 16 novel molecules, in particular in the pyridinium class of compounds, to further address this peculiar phenomenon. We found molecules with very short RTs (e.g., 0.34 min for 37) and much longer RTs (e.g., 105 min for 38). This enabled us to construct a k(on)-k(off)-K-D kinetic map for all compounds and subsequently divide the map into four provisional quadrants, providing a possible framework for a further and more precise categorization of K(v)11.1 blockers. Additionally, two representative compounds (21 and 38) were tested in patch clamp assays, and their RTs were linked to their functional IC50 values. Our findings strongly suggest the importance of the simultaneous study of ligand affinities and kinetic parameters, which may help to explain and predict K(v)11.1-mediated cardiotoxicity.

  DOI：

  10.1021/acs.jmedchem.5b00518

文献信息

• Exhaustive Suzuki–Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters
  作者：Sébastien Laulhé、J. Miles Blackburn、Jennifer L. Roizen

  DOI：10.1039/c7cc00997f

  日期：——

  A novel Suzuki–Miyaura protocol is described that enables the exhaustive alkylation of polychlorinated pyridines. This method facilitates a formal synthesis of normuscopyridine and the rapid assembly of a dumbbell shaped portion of a [2]rotaxane.

  描述了一种新颖的Suzuki-Miyaura方案，该方案可实现多氯吡啶的彻底烷基化。该方法促进了正霉基吡啶的正式合成和[2]轮烷的哑铃状部分的快速组装。
• Selective and Serial Suzuki–Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
  作者：Sébastien Laulhé、J. Miles Blackburn、Jennifer L. Roizen

  DOI：10.1021/acs.orglett.6b02323

  日期：2016.9.2

  availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki–Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert

  在交叉偶联反应中，Suzuki-Miyaura转化因其实际优势而脱颖而出，其中包括商业上可获得的试剂和所需试剂的低毒性，温和的反应条件以及官能团的相容性。然而，几乎没有条件可用于烷基硼酸或酯与芳基卤化物，特别是2-吡啶基卤化物的交联。在这里，我们描述了两个新颖的Suzuki-Miyaura协议，它们能够选择性地转换多氯代芳烃，重点是将2，6-二氯吡啶转化为2-氯-6-烷基吡啶或2-芳基-6-烷基吡啶的反应。
• KATALYSATORSYSTEME VOM TYP DER ZIEGLER-NATTA-KATALYSATOREN UND EIN VERFAHREN ZU DEREN HERSTELLUNG
  申请人：Basell Polyolefine GmbH

  公开号：EP1326899A2

  公开（公告）日：2003-07-16
• Catalyst systems of the ziegler-natta type and a method for production thereof
  申请人：Fottinger Klaus

  公开号：US20050075241A1

  公开（公告）日：2005-04-07

  A method for production of catalytic systems of the Ziegler-Natta type is characterised in comprising the following steps: A) bringing an inorganic metal oxide and a magnesium compound of formula MgR n X 2-n into contact, where X=independently, fluorine, chlorine, bromine, iodine, hydrogen, NR 2 , OR, SR, SO 3 R or OC(O)R and R=independently, C 1 -C 20 linear, branched, or cyclic alkyl, a C 2 -C 10 alkenyl, an alkylaryl with 1-10 C atoms in the alkyl group and 6-20 C atoms in the aryl group, or a C 6 -C 18 aryl and n=1 or 2, then, B) bringing the intermediate product obtained in step A) into contact with a halogenating reagent, C) bringing the intermediate product obtained in step B) into contact with a) a tetravalent titanium compound, b) a metallo-organic compound of group 3 of the periodic system and c) optionally, an electron-donor compound and D) washing the product obtained in step C) with an aprotic solvent. The invention further relates to a catalytic system obtained as above and a method for the polymerisation of olefins.
• [DE] KATALYSATORSYSTEME VOM TYP DER ZIEGLER-NATTA-KATALYSATOREN UND EIN VERFAHREN ZU DEREN HERSTELLUNG<br/>[EN] CATALYTIC SYSTEMS OF THE ZIEGLER-NATTA TYPE AND METHOD FOR PRODUCTION THEREOF<br/>[FR] SYSTEMES CATALYSEURS ZIEGLER-NATTA, ET LEUR PROCEDE DE PRODUCTION
  申请人：BASELL POLYOLEFINE GMBH

  公开号：WO2002032969A2

  公开（公告）日：2002-04-25

  Verfahren zur Herstellung von Katalysatorsystemen vom Typ der Ziegler-Natta-Katalysatoren, dadurch gekennzeichnet, dass es folgende Schritte umfasst: A) Kontaktieren eines anorganischen Metalloxides mit einer Magnesiumverbindung MgRnX2-n, worin X unabhängig voneinander Fluor, Chlor, Brom, Jod, Wasserstoff, NR2, OR, SR, SO3R oder OC(O)R, und R unabhängig voneinander ein C1C20 lineares, verzweigtes oder cyclisches Alkyl, ein C2-C10-Alkenyl, ein Alkylaryl mit 1-10 C-Atomen im Alkylrest und 6-20 C-Atomen im Arylrest oder ein C6-C18-Aryl bedeutet und n gleich 1 oder 2 ist, und anschliessend, B) Kontaktieren der nach Schritt A) erhaltenen Zwischenstufe mit einem Halogenierungsreagenz, C) Kontaktieren der nach Schritt B) erhaltenen Zwischenstufe mit a) einer tetravalenten Titanverbindung, b) einer mallorganischen Verbindung der Gruppe 3 des Periodensystems und c) gegebenenfalls einer Elektronendonorverbindung, und D) Waschen des nach Schritt C) erhaltenen Produktes mit einem aprotischen Lösungsmittel, damit erhältliche Katalysatorsysteme und ein Verfahren zur Polymerisation von Olefinen.