ethyl 3-methylthio-5-phenyl-1,2,4-triazine-6-carboxylate | 865445-63-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 3-methylthio-5-phenyl-1,2,4-triazine-6-carboxylate
• 英文别名: Ethyl 3-methylsulfanyl-5-phenyl-1,2,4-triazine-6-carboxylate；ethyl 3-methylsulfanyl-5-phenyl-1,2,4-triazine-6-carboxylate
• CAS: 865445-63-2
• 化学式: C₁₃H₁₃N₃O₂S
• 分子量: 275.331
• InChiKey: JPVXVSMYEYCDOO-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64 °C
• 沸点：
  489.3±47.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  90.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-methylthio-5-phenyl-1,2,4-triazine-6-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到
  参考文献：
  名称：

  A convenient synthesis of pyridine and 2,2′-bipyridine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.11.090
• 作为产物：
  描述：

  S-methylthiosemicarbazide hydrochloride 、 ethyl 2,3-dioxo-3-phenylpropanoate 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到ethyl 3-methylthio-5-phenyl-1,2,4-triazine-6-carboxylate
  参考文献：
  名称：

  A convenient synthesis of pyridine and 2,2′-bipyridine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.11.090

文献信息

• 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.
• 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.