2-(4-Nitro-phenyl)-N-(2-oxo-2-pyridin-3-yl-ethyl)-acetamide | 202873-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-Nitro-phenyl)-N-(2-oxo-2-pyridin-3-yl-ethyl)-acetamide
• 英文别名: 2-(4-nitrophenyl)-N-(2-oxo-2-pyridin-3-ylethyl)acetamide
• CAS: 202873-14-1
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: CVBGGPAWTKOLFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-Nitro-phenyl)-N-(2-oxo-2-pyridin-3-yl-ethyl)-acetamide 在 palladium on activated charcoal ammonium hydroxide 、 yeast Candida sorbophilia 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 28.0~40.0 ℃ 、137.9 kPa 条件下， 反应 51.0h， 生成 2-(4-{4-[4-(3-Cyclopentyl-propyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-benzenesulfonylamino}-phenyl)-N-((R)-2-hydroxy-2-pyridin-3-yl-ethyl)-acetamide
  参考文献：
  名称：

  Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

  摘要：

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01353-2
• 作为产物：
  描述：

  (1E)-N-羟基-1-(3-吡啶基)乙烷亚胺 在 盐酸 、 potassium ethoxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 生成 2-(4-Nitro-phenyl)-N-(2-oxo-2-pyridin-3-yl-ethyl)-acetamide
  参考文献：
  名称：

  Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist

  摘要：

  A chemoenzymatic synthesis of beta(3) agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01353-2