ethyl 6-phenyl-[2,2']-bipyridine-5-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 6-phenyl-[2,2']-bipyridine-5-carboxylate
• 英文别名: ethyl 6-phenyl-2,2'-bipyridine-5-carboxylate；ethyl 6-phenyl[2,2']bipyridyl-5-carboxylate；Ethyl 2-phenyl-6-pyridin-2-ylpyridine-3-carboxylate
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: OGZDGLNBRCIJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-chloro-3-oxo-3-phenylpropionate 在 乙醇 、 copper diacetate 、 potassium hydrogencarbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 264.0h， 生成 ethyl 6-phenyl-[2,2']-bipyridine-5-carboxylate
  参考文献：
  名称：

  2,2'-联吡啶衍生物的便捷合成

  摘要：

  从相应的α-氯-β-酮酯6制备吡啶甲酸7。使用aza Diels-Alder反应，通过三嗪9将酯7转化为2,2'-联吡啶衍生物10。

  DOI：

  10.1016/j.tetlet.2007.07.153

文献信息

• Four-Component Synthesis of Functionalized 2,2′-Bipyridines Based on the Blaise Reaction
  作者：Hans-Ulrich Reissig、Paul Hommes、Phillip Jungk

  DOI：10.1055/s-0030-1260304

  日期：2011.10

  In situ C-acylation of the Blaise intermediate - as reported by Lee and coworkers - provides α-acyl-β-enamino esters that are versatile building blocks for the preparation of N-heterocycles. The corresponding N-acylated β-ketoenamides can be employed in the synthesis of 4-hydroxypyridine derivatives. N-Acylation of the α-acyl-β-enamino esters with 2-picolyl chloride furnished β-keto­enamides, and the

  Lee和他的同事报道，Blaise中间体的原位C-酰化作用提供了α-酰基-β-烯氨基酯，这些酯是制备N杂环的通用构建基块。相应的N-酰化的β-酮烯酰胺可用于合成4-羟基吡啶衍生物。α-酰基-β-烯胺酸酯与2-吡啶甲基氯的N-酰化提供了β-酮烯酰胺，随后的TMSOTf /碱促进的分子内缩合反应导致了4-羟基-2,2'-联吡啶衍生物。转化为2,2'-联吡啶-4-基壬酸酯可以实现进一步的功能化，例如钯催化的偶联反应。 缩合-2,2'-联吡啶-β-酮烯酰胺-多组分反应-壬酸酯-吡啶
• Synthesis of pyridine and 2,2′-bipyridine derivatives from the aza Diels–Alder reaction of substituted 1,2,4-triazines
  作者：Stephen P. Stanforth、Brian Tarbit、Michael D. Watson

  DOI：10.1016/j.tet.2004.07.024

  日期：2004.9

  derivatives 6b–d respectively (59–72%) and in the presence of 2,3-dihydrofuran 7 yielding the lactones 10b–d (39–44%). The 2,2′-bipyridine derivatives 6e–g were similarly obtained in good yield (81–87%) from the reaction of amidrazone 1b and tricarbonyl derivatives 2b–d in the presence of 2,5-norbornadiene 5.

  在2,5-降冰片二烯5存在下，咪唑酮1a和三羰基衍生物2b – d在沸腾的乙醇中反应，分别得到吡啶衍生物6b – d（59–72％）和在2,3-二氢呋喃7存在下，生成吡啶衍生物6b – d。内酯10b – d（39–44％）。类似地，在2，5-降冰片二烯5存在下，胺1b与三羰基衍生物2b - d的反应也可以以高收率（81-87％）获得2,2'-联吡啶衍生物6e - g。
• A convenient synthesis of pyridine and 2,2′-bipyridine derivatives
  作者：Marta Altuna-Urquijo、Alexander Gehre、Stephen P. Stanforth、Brian Tarbit

  DOI：10.1016/j.tet.2008.11.090

  日期：2009.1

  alpha-Chloro-alpha-acetoxy-beta-keto-esters 9 were readily prepared from beta-keto-esters 6 in good overall yields. These compounds reacted as alpha,beta-diketo-ester equivalents 2 with amidrazones 1 yielding triazines 3, generally in good yields. Picolinates 10 provided an alternative source of alpha,beta-diketo-ester equivalents 2 when treated with copper(II) acetate. A 'one-pot' reaction of the alpha,beta-diketo-ester equivalents 2 with amidrazones 1 in the presence of 2,5-norbornadiene 5 in boiling ethanol yielded the pyridines 4 and 2,2'-bipyridines 4 (R-1=2-pyridyl) directly without the need to isolate the corresponding triazines 3. Triazine 3c reacted with the aza-dienophiles 13 and 17 affording the products 16 and 18, respectively, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 2,2′-bipyridyl derivatives using aza Diels–Alder methodology
  作者：Stephen P. Stanforth、Brian Tarbit、Michael D. Watson

  DOI：10.1016/s0040-4039(02)02670-9

  日期：2003.1

  Amidrazone 1 and the tricarbonyl derivatives 2a-c gave the triazines 3a-c, respectively, which reacted with 2,5-norbornadiene 4 in boiling ethanol yielding the corresponding novel 2,2'-bipyridines 5a-c in good yield. Triazine 6 gave the 2,2'-bipyridyl derivative 7 (65%) with compound 4 in 1,2-dichlorobenzene at 140degreesC. (C) 2003 Elsevier Science Ltd. All rights reserved.
• The preparation of 1,2,4-triazines from α,β-diketo-ester equivalents and their application in pyridine synthesis
  作者：Marta Altuna-Urquijo、Stephen P. Stanforth、Brian Tarbit

  DOI：10.1016/j.tetlet.2005.06.163

  日期：2005.9

  The alpha-Chloro-alpha-acetoxy-beta-keto-esters were prepared from beta-keto-esters in good overall yields. These compounds reacted as alpha,beta-diketo-ester equivalents with amidrazones yielding triazines, generally in good yields, or with an amidrazone and 2,5-norbornadiene in a one-pot aza Diels-Alder reaction to give the corresponding pyridines. (c) 2005 Elsevier Ltd. All rights reserved.