ethyl 6-methylthio-2-phenylpyridine-3-carboxylate | 1116572-39-4

• 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-methylthio-2-phenylpyridine-3-carboxylate
• 英文别名: Ethyl 6-methylsulfanyl-2-phenylpyridine-3-carboxylate；ethyl 6-methylsulfanyl-2-phenylpyridine-3-carboxylate
• CAS: 1116572-39-4
• 化学式: C₁₅H₁₅NO₂S
• 分子量: 273.356
• InChiKey: DMOAHPQUGLCCDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-methylthio-2-phenylpyridine-3-carboxylate 在 sodium perborate 、 溶剂黄146 作用下， 反应 4.0h， 以78%的产率得到ethyl 6-methanesulfinyl-2-phenylpyridine-3-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
• 作为产物：
  描述：

  ethyl 3-methylthio-5-phenyl-1,2,4-triazine-6-carboxylate 、 2,5-降冰片二烯 以 邻二氯苯 为溶剂， 反应 24.0h， 以88%的产率得到ethyl 6-methylthio-2-phenylpyridine-3-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.