ethyl 5-propyl-3-(2-pyridyl)-1,2,4-triazine-6-carboxylate | 532946-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: ethyl 5-propyl-3-(2-pyridyl)-1,2,4-triazine-6-carboxylate
• 英文别名: Ethyl 5-propyl-3-pyridin-2-yl-1,2,4-triazine-6-carboxylate
• CAS: 532946-67-1
• 化学式: C₁₄H₁₆N₄O₂
• 分子量: 272.307
• InChiKey: HAYGWZKMRWLEJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  477.2±55.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-降冰片二烯 、 ethyl 5-propyl-3-(2-pyridyl)-1,2,4-triazine-6-carboxylate 以 乙醇 为溶剂， 生成 ethyl 6-propyl-[2,2']-bipyridine-5-carboxylate
  参考文献：
  名称：

  Synthesis of 2,2′-bipyridyl derivatives using aza Diels–Alder methodology

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)02670-9
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 磺酰氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 5-propyl-3-(2-pyridyl)-1,2,4-triazine-6-carboxylate
  参考文献：
  名称：

  The preparation of 1,2,4-triazines from α,β-diketo-ester equivalents and their application in pyridine synthesis

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.06.163

文献信息

• A convenient synthesis of 2,2′-bipyridine derivatives
  作者：Alexander Gehre、Stephen P. Stanforth、Brian Tarbit

  DOI：10.1016/j.tetlet.2007.07.153

  日期：2007.9

  Picolinates 7 were prepared from the corresponding α-chloro-β-keto-esters 6. Esters 7 were converted into 2,2′-bipyridine derivatives 10 via triazines 9 using an aza Diels–Alder reaction.

  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。
• 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.