2,6-二甲基-4-苯基烟酸乙酯 | 4350-44-1

• 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
• 中文名称: 2,6-二甲基-4-苯基烟酸乙酯
• 英文名称: ethyl 2,6-dimethyl-4-phenylpyridine-3-carboxylate
• 英文别名: 2,6-Dimethyl-4-phenyl-nicotinic acid ethyl ester
• CAS: 4350-44-1
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: OQVGXASMCWLVHD-UHFFFAOYSA-N

物化性质

• 沸点：
  147 °C(Press: 1.5 Torr)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2,6-二甲基-4-苯基烟酸乙酯 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以38%的产率得到2,6-Dimethyl-4-phenyl-pyridin-carbonsaeure-(3)
  参考文献：
  名称：

  Non-peptide NK1 receptor ligands based on the 4-phenylpyridine moiety

  摘要：

  The quinoline nucleus of the previously described 4-phenylquinoline-3-carboxamides NK1 receptor ligands 7 has been transformed into either substituted or azole-(i.e., triazole or tetrazole) fused pyridine moieties of compounds 9 and 10, respectively, in order to obtain NK1 receptor ligands showing lower molecular weight or higher hydrophilicity. The program of molecular manipulations produced NK1 receptor ligands showing affinity in the nanomolar range. In particular, 4-methyl-1-piperazinyl derivative 9j showed an IC50 value of 4.8 nM and was proved to behave as a NK1 antagonist blocking Sar(9)-SP-sulfone induced proliferation and migration of microvascular endothelial cells. Therefore, compound 9j has been labeled with [C-11]CH3I (t(1/2) = 20.4 min, beta(+) = 99.8%) starting from the corresponding des-methyl precursor 9i using with a radiochemical yield of about 10% (not decay corrected) and a specific radioactivity > 1 Ci/mu mol in order to be used as a radiotracer in next PET studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.031
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2,6-二甲基-4-苯基烟酸乙酯
  参考文献：
  名称：

  Hantzsch, Chemische Berichte, 1884, vol. 17, p. 2904

  摘要：

  DOI：

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。
• Preparation of π-deficient heteroarylzinc halides by oxidative addition of active zinc and its palladium-catalyzed reaction
  作者：Takao Sakamoto、Yoshinori Kondo、Naoko Murata、Hiroshi Yamanaka

  DOI：10.1016/s0040-4020(01)80174-5

  日期：1993.1

  The oxidative addition of active zinc to iodo- and bromo-substituted π-deficient heteroarenes such as pyridine, pyrimidine, and quinoline gave the corresponding heteroarylzinc halides which were transformed to the arylated and benzoylated derivatives by palladium-catalyzed reaction.

  将活性锌氧化加到碘和溴取代的π缺失的杂芳烃上，例如吡啶，嘧啶和喹啉，得到相应的杂芳基卤化锌，它们通过钯催化的反应转化为芳基化和苯甲酰化的衍生物。
• A New Modification of the Bohlmann-Rahtz Pyridine Synthesis
  作者：Mark C. Bagley、James W. Dale、Justin Bower

  DOI：10.1055/s-2001-15140

  日期：——

  A range of highly functionalised pyridines is prepared from enamino and alkynones in a single synthetic step by the use of acetic acid or amberlyst 15 ion exchange resin at 50 °C.

  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。
• Ionic liquid promoted simple and efficient synthesis of β-enamino esters and β-enaminones from 1,3-dicarbonyl compounds – One-pot, three-component reaction for the synthesis of substituted pyridines
  作者：Ganesan Karthikeyan、Paramasivan T Perumal

  DOI：10.1139/v05-186

  日期：2005.10.1

  A facile enamination of 1,3-dicarbonyl compounds with amines has been developed that affords good to excellent yields of β-enamino esters and β-enaminones using Brønsted acidic ionic liquid 1-methylimidazolium trifluoroacetate ([Hmim]⁺Tfa^–) at room temperature. This methodology has been extended for the synthesis of substituted pyridines in excellent yield by a one-pot, three-component reaction of 1,3-dicarbonyl compounds, ammonium acetate, and alkynone in the presence of [Hmim]⁺Tfa^–.Key words: ionic liquid, β-enaminones, β-enamino esters, 1,3-dicarbonyl compounds, amines, pyridines.

  已开发出一种简便的方法，利用Brønsted酸性离子液体1-甲基咪唑三氟乙酸盐([Hmim]⁺Tfa^–)在室温下与胺类化合物进行1,3-二羰基化合物的反应，得到良好至优异产率的β-烯胺酯和β-烯酮。该方法已扩展到通过在[Hmim]⁺Tfa^–存在下进行1,3-二羰基化合物、醋酸铵和炔酮的一锅法三组分反应，以优异产率合成取代吡啶。关键词：离子液体，β-烯酮，β-烯胺酯，1,3-二羰基化合物，胺类，吡啶。