2,3'-bipyridine-1-oxide | 39182-27-9

• 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: 2,3'-bipyridine-1-oxide
• 英文别名: 2-(3'-pyridinyl)pyridine N-oxide；Isonicoten-N-oxid；[2,3']bipyridinyl 1-oxide；2,3'-dipyridyl N-oxide；1-oxido-2-pyridin-3-ylpyridin-1-ium
• CAS: 39182-27-9
• 化学式: C₁₀H₈N₂O
• 分子量: 172.186
• InChiKey: SGUIQNQGCLEUEN-UHFFFAOYSA-N

物化性质

• 沸点：
  436.2±20.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1'-methyl-2,3'-bipyridinium-1-oxide tosylate 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以40%的产率得到2,3'-bipyridine-1-oxide
  参考文献：
  名称：

  N-methylation and N-oxidation of the less reactive nitrogen atom of a 2,3′-bipyridine. Two general methods for polyazines

  摘要：

  5-Carbamoyl-2,3'-bipyridine model compound was N-methylated or N-oxidized at the less reactive 2-pyridyl ring for the first time. Two different schemes were developed.

  DOI：

  10.1016/0040-4020(95)00074-i

文献信息

• Activation of Unstrained Ketone C(O)–C Bond: 1,2-Nucleophilic Addition Followed by β-Carbon Elimination Strategy
  作者：Qiang Li、Yiwen Xu、Yang Long、Sun Li、Buyi Xu、Ying Xia、Xiangge Zhou

  DOI：10.1021/acscatal.3c01602

  日期：2023.6.16

  moiety followed by β-C elimination strategy was less studied. Here a palladium-catalyzed C–C bond activation of an unstrained ketone enabled by a removable directing group through β-C elimination to synthesize 2-arylpyridine is described. The protocol features wide substrate scope with yields up to 95%, good functional group tolerance, and functionality of natural products. The 2-arylpyridine N-oxide

  过渡金属催化的 C-C 键活化已成为一种日益有效的分子骨架重组方法。酮作为一种多功能的功能分子，其 C-C 键活化反应已被广泛研究。然而，大多数无张力酮的C-C键活化通常遵循氧化加成策略，而羰基部分的亲核1,2-加成随后β-C消除策略的研究较少。这里描述了钯催化的无张力酮的 C-C 键活化，通过可去除的导向基团通过 β-C 消除来合成 2-芳基吡啶。该方案具有底物范围宽、收率高达95%、良好的官能团耐受性以及天然产物的功能等特点。2-芳基吡啶N-氧化物产物在温和的反应条件下可以很容易地转化为相应的2-芳基吡啶。
• Studies on Organometallic Compounds. IX. Synthesis of Bipyride N-Oxides and Terpyridines by Palladium Catalyzed Cross-Coupling Reaction of Trimethylstannylpyridines with Bromopyridines
  作者：Yutaka Yamamoto、Takuo Tanaka、Masayoshi Yagi、Masayuki Inamoto

  DOI：10.3987/com-94-s4-1

  日期：——

  Reaction of trimethylstannylpyridines with bromopyridines in the presence of Pd(PPh(3))(4) directed toward a practical use was accomplished, giving all nine pyridinylpyridine N-oxides in satisfactory yields. Similarly, nicotelline and 2,2':6',2 ''-terpyridine were produced in good yields.
• KURBATOV, YU. V.;ABDULLAEV, SH. V.;TSUKERVANIK, V. S.;BAZHENOVA, N. S., FIZ.-XIM. ISSLED. SINTETICH. I PRIROD. SOEDIN., SAMARKAND, 1983, 12-16
  作者：KURBATOV, YU. V.、ABDULLAEV, SH. V.、TSUKERVANIK, V. S.、BAZHENOVA, N. S.

  DOI：——

  日期：——
• N-methylation and N-oxidation of the less reactive nitrogen atom of a 2,3′-bipyridine. Two general methods for polyazines
  作者：John A. Zoltewicz、Michael P. Cruskie

  DOI：10.1016/0040-4020(95)00074-i

  日期：1995.3

  5-Carbamoyl-2,3'-bipyridine model compound was N-methylated or N-oxidized at the less reactive 2-pyridyl ring for the first time. Two different schemes were developed.