ethyl 2,6-dimethyl-4-ethylpyridine-3-carboxylate

• 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: ethyl 2,6-dimethyl-4-ethylpyridine-3-carboxylate
• 英文别名: Ethyl 4-ethyl-2,6-dimethylpyridine-3-carboxylate
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: FUDCGXXRFRGTGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-己炔-2-酮 、 3-氨基巴豆酸乙酯 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 以85%的产率得到ethyl 2,6-dimethyl-4-ethylpyridine-3-carboxylate
  参考文献：
  名称：

  A New Modification of the Bohlmann-Rahtz Pyridine Synthesis

  摘要：

  通过在50 °C下使用醋酸或Amberlyst 15离子交换树脂，从烯胺和炔酮中在单一步骤中合成出一系列高功能化的吡啶。

  DOI：

  10.1055/s-2001-15140

文献信息

• Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann–Rahtz reaction
  作者：Mark C. Bagley、Christian Brace、James W. Dale、Maren Ohnesorge、Nathan G. Phillips、Xin Xiong、Justin Bower

  DOI：10.1039/b203397f

  日期：2002.7.11

  New facile experimental procedures for the preparation of 2,3,4,6-tetrasubstituted pyridines in a single synthetic step have been developed. Thus, an enamino ester and alkynone react by Michael addition–cyclodehydration in a heterocyclisation process that is catalysed by acetic acid, Amberlyst 15 ion exchange resin, zinc(II) bromide or ytterbium(III) triflate. The new one-step Brønsted or Lewis acid-catalysed Bohlmann–Rahtz reaction is a simple, direct and highly expedient method for the synthesis of pyridines that proceeds at a lower reaction temperature and avoids the need to isolate reaction intermediates.

  新近开发了一种简便的实验程序，用于在单一合成步骤中制备2,3,4,6-四取代吡啶。在此过程中，烯胺酯和炔酮通过迈克尔加成-环脱水反应在杂环化过程中催化，催化剂可为乙酸、Amberlyst 15离子交换树脂、锌(II)溴化物或镱(III)三氟甲磺酸盐。这种新型的单步布伦斯特德或路易斯酸催化Bohlmann-Rahtz反应，是一种直接、简单且高效的合成吡啶的方法，其反应温度较低，且无需分离反应中间体。
• New<i>N</i>-Halosuccinimide-Mediated Reactions for the Synthesis of Pyridines
  作者：Mark C. Bagley、Christian Glover、Eleanor A. Merritt、Xin Xiong

  DOI：10.1055/s-2004-820019

  日期：——

  5-Bromo-2,6-dialkylpyridine-4-carboxylates are generated in excellent yield by the Michael addition of enaminoesters and ethynyl ketones followed by bromocyclization using N-bromo­succinimide within 1 hour at 0 °C. Treatment of the same aminopentadienone intermediates with N-iodosuccinimide facilitates a low temperature cyclodehydration under very mild conditions to give 2,3,6-trisubstituted pyridines with total regiocontrol.

  5-溴-2,6-二烷基吡啶-4-羧酸酯通过酮炔与酰胺酯的迈克尔加成反应生成，随后在0°C下用N-溴琥珀酰亚胺进行溴化环化，收率极高，反应仅需1小时。将相同的氨基五烯酮中间体与N-碘琥珀酰亚胺处理，可在非常温和的条件下促进低温环脱水反应，生成具有完全区域选择性的2,3,6-三取代吡啶。
• Novel rare earth metal cryptates which are not very sensitive to the fluorescence quenching
  申请人：——

  公开号：US20040092726A1

  公开（公告）日：2004-05-13

  The invention relates to a process for reducing the fluorescence quenching caused by the measuring medium in a fluorescence assay, by introducing into said medium of rare earth metal cryptates which are not very sensitive to this fluorescence quenching, said rare earth metal cryptates comprising at least one pyridine radical which is substituted one or more times or unsubstituted. The invention also relates to novel rare earth metal cryptates which are not very sensitive to the fluorescence quenching caused by the measuring medium.

  该发明涉及一种减少荧光测定中测量介质引起的荧光猝灭的过程，通过向该介质中引入对该荧光猝灭不太敏感的稀土金属螯合物，所述稀土金属螯合物包括至少一个吡啶基，该吡啶基被取代一次或多次或未取代。该发明还涉及一种新型对测量介质引起的荧光猝灭不太敏感的稀土金属螯合物。
• A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines
  作者：Mark C. Bagley、James W. Dale、Justin Bower

  DOI：10.1039/b203900a

  日期：2002.7.25

  condensation of a beta-ketoester, ammonia and an alkynone in the presence of a Brønsted or Lewis acid or Amberlyst 15 ion exchange resin provided 2,3,6-trisubstituted or 2,3,4,6-tetrasubstituted pyridines directly in good yield and with total regiocontrol.

  在Brønsted或Lewis酸或Amberlyst 15离子交换树脂存在下，β-酮酸酯，氨和炔酮的一锅三组分缩合可提供2,3,6-三取代或2,3,4,6-直接取代四取代吡啶，收率高，且具有区域控制能力。
• A new mild method for the one-pot synthesis of pyridines
  作者：Xin Xiong、Mark C Bagley、Krishna Chapaneri

  DOI：10.1016/j.tetlet.2004.06.061

  日期：2004.8

  Polysubstituted pyridines are prepared in good yield and with total regiocontrol by the one-pot reaction of an alkynone, 1,3-dicarbonyl compound and ammonium acetate in alcoholic solvents. This new three-component heteroannulation reaction proceeds under mild conditions in the absence of an additional acid catalyst and has been used in the synthesis of dimethyl sulfomycinamate, the acidic methanolysis

  多取代的吡啶以高收率制备，并通过炔醇，1，3-二羰基化合物和乙酸铵在醇溶剂中的一锅反应，具有完全的区域控制性。这种新的三组分杂环化反应可在温和条件下在不使用其他酸催化剂的条件下进行，已用于合成硫代肽抗生素的硫霉素家族的酸性甲醇分解降解产物二硫代丝氨酸。