(4-硝基-苯基)-[3]吡啶基酮 | 110141-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4-硝基-苯基)-[3]吡啶基酮
• 英文名称: (4-nitro-phenyl)-[3]pyridyl ketone
• 英文别名: (4-Nitro-phenyl)-[3]pyridyl-keton；3-(4-nitrobenzoyl)pyridine；(4-Nitrophenyl)-pyridin-3-ylmethanone
• CAS: 110141-52-1
• 化学式: C₁₂H₈N₂O₃
• 分子量: 228.207
• InChiKey: SBFAVQPGDJEDCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-硝基-苯基)-[3]吡啶基酮 在 stannous chloride 作用下， 以 乙醇 为溶剂， 以76%的产率得到3-(4-aminobenzoyl)pyridine
  参考文献：
  名称：

  Therapeutic amides

  摘要：

  酰胺具有以下化学式I：##STR1## 其中E、X、R.sup.2和R.sup.3的含义如规范中所述，并且其药学上可接受的盐和在体内可水解的酯，可用于治疗尿失禁。还提供了制备这些酰胺的方法和含有它们的药物组合物。

  公开号：

  US05272163A1
• 作为产物：
  描述：

  3-(4'-nitrobenzyl)pyridine 在 permanganate(VII) ion 作用下， 生成 (4-硝基-苯基)-[3]吡啶基酮
  参考文献：
  名称：

  Bryans; Pyman, Journal of the Chemical Society, 1929, p. 550

  摘要：

  DOI：

文献信息

• Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry
  作者：Kumiko Takeuchi、Jonathan W. Paschal、Richard J. Loncharich

  DOI：10.1021/jo00106a029

  日期：1995.1

  Investigation of the stereoselectivity observed in the Wittig reaction of aromatic ketones with ''nonstabilized'' phosphonium ylides revealed that the nature of the substituent on the phenyl ring of phenyl S-pyridyl ketone determined the stereoselectivity. Generally the Wittig reaction of such ketones with carboxy phosphonium ylides proceeded preferentially to yield (Z)-olefin, albeit with modest selectivity. However, the reaction with aryl sulfonamido-substituted aromatic ketones resulted in high (E)-stereoselectivity. In order to understand the origin of this high (E)-selectivity, a semiempirical conformational analysis of the four uncharged diastereomeric oxaphosphetane intermediates was performed with a cumulatively modified sampling procedure to generate initial conformations, followed by full energy optimization. Computational studies of the unsubstituted and 4-nitrophenyl-substituted oxaphosphetane intermediates were consistent with the low (Z)stereoselectivity observed. The results in the calculations of the aryl sulfonamido-substituted intermediate likewise were consistent with the high (E)-stereoselectivity observed. Calculations of the potassium-coordinated acid anion of the latter species were also performed. All calculations supported interaction of the sulfonamido and carboxylate groups by either hydrogen bonding or salt bridge formation which appears to effect the final stereochemical outcome. Furthermore, we investigated the stereoselectivity of Wittig reactions in which the sulfonamido NH or the carboxylate were removed. In both cases, the (Z)-olefin was formed preferentially, thereby supporting the existence of intramolecular hydrogen bonding or salt bridge formation.
• US5272163A
  申请人：——

  公开号：US5272163A

  公开（公告）日：1993-12-21
• US5382598A
  申请人：——

  公开号：US5382598A

  公开（公告）日：1995-01-17
• US5474999A
  申请人：——

  公开号：US5474999A

  公开（公告）日：1995-12-12
• US5565465A
  申请人：——

  公开号：US5565465A

  公开（公告）日：1996-10-15