ethyl 2,6-dimethyl-4-(trimethylsilyl)pyridine-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-(trimethylsilyl)pyridine-3-carboxylate
• 英文别名: Ethyl 2,6-dimethyl-4-trimethylsilylpyridine-3-carboxylate
• 化学式: C₁₃H₂₁NO₂Si
• 分子量: 251.401
• InChiKey: ZXTRBLUEIVHOQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  4-三甲基硅基-3-丁炔-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79%的产率得到ethyl 2,6-dimethyl-4-(trimethylsilyl)pyridine-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。
• 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。
• Synthesis of Pyridines and Pyrido[2,3-d]pyrimidines by the Lewis Acid Catalysed Bohlmann-Rahtz Heteroannulation Reaction
  作者：Mark C. Bagley、James W. Dale、David D. Hughes、Maren Ohnesorge、Nathan G. Phillips、Justin Bower

  DOI：10.1055/s-2001-17447

  日期：——

  Lewis acids catalyse the Bohlmann-Rahtz heteroannulation reaction to generate highly functionalised pyridines from enamino esters and alkynones in a single synthetic step. Of the catalysts studied, ytterbium(III)trifluoromethanesulfonate and zinc(II) bromide are the two most efficient for the synthesis of pyridines and pyrido[2,3-d]pyrimidines, from ethyl β-aminocrotonate or 2,6-diaminopyrimidin-4-one respectively, in up to 94% yield.

  路易斯酸催化了 Bohlmann-Rahtz 异annulation 反应，只需一个合成步骤就能从烯酰胺酯和炔酮中生成高官能度的吡啶。在所研究的催化剂中，三氟甲磺酸镱和溴化锌是分别从δ-氨基巴豆酸乙酯或 2,6-二氨基嘧啶-4-酮合成吡啶和吡啶并[2,3-d]嘧啶的两种最有效的催化剂，产率高达 94%。
• One-Pot Multistep Bohlmann−Rahtz Heteroannulation Reactions:  Synthesis of Dimethyl Sulfomycinamate
  作者：Mark C. Bagley、Krishna Chapaneri、James W. Dale、Xin Xiong、Justin Bower

  DOI：10.1021/jo048106q

  日期：2005.2.1

  The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.
• A new one-step synthesis of pyridines under microwave-assisted conditions
  作者：Mark C Bagley、Rebecca Lunn、Xin Xiong

  DOI：10.1016/s0040-4039(02)01975-5

  日期：2002.11

  Tri- or tetrasubstituted pyridines are prepared by microwave irradiation of ethyl beta-aminocrotonate and various alkynones in a single synthetic step and with total control of regiochemistry. This new one-pot Bohlmann-Rahtz procedure conducted at 170degreesC in a self-tunable microwave synthesiser gives superior yields to similar experiments conducted using conductive-heating techniques in a sealed tube and can be carried out in the presence of a Bronsted or Lewis acid catalyst. (C) 2002 Published by Elsevier Science Ltd.