2,3-dihydro-1'-p-bromophenylsulfonylspiro(1,4-dioxino[2,3-b]pyridine)-3,3'-pyrrolidine | 590375-70-5

• 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: 2,3-dihydro-1'-p-bromophenylsulfonylspiro(1,4-dioxino[2,3-b]pyridine)-3,3'-pyrrolidine
• 英文别名: 1'-(4-bromophenyl)sulfonylspiro[2H-[1,4]dioxino[2,3-b]pyridine-3,3'-pyrrolidine]
• CAS: 590375-70-5
• 化学式: C₁₆H₁₅BrN₂O₄S
• 分子量: 411.276
• InChiKey: YHXSLSDNSFTCMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-1'-p-bromophenylsulfonylspiro(1,4-dioxino[2,3-b]pyridine)-3,3'-pyrrolidine 在 lithium aluminium tetrahydride 、 三乙胺 、 potassium iodide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2,3-dihydro-1'-[4-(8-azaspiro[4,5]decane-7,9-dione)butyl]spiro(1,4-dioxino[2,3-b]pyridine)-3,3'-pyrrolidine
  参考文献：
  名称：

  Synthesis of new compounds containing the 2,3-dihydro[1,4]dioxino[2,3-b]pyridine heterocyclic system as a substructure

  摘要：

  2,3-Dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,3'-pyrrolidine (8A) and 2,3-dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,4 piperidine (9A) have been synthesized from 2-chloro-3-pyridinol. The corresponding 2,3' (8B) and 2,4' (9B) isomers were obtained via the Smiles rearrangement, while 9B was also selectively synthesized from 2-nitro-3-pyridinol. The separation of the isomers A and B under the sulfamide form was carried out by flash column chromatography.

  DOI：

  10.1016/s0040-4020(03)00513-1
• 作为产物：
  描述：

  5-苄基-1-氧杂-5-氮杂螺[2.4]庚烷 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 2,3-dihydro-1'-p-bromophenylsulfonylspiro(1,4-dioxino[2,3-b]pyridine)-3,3'-pyrrolidine
  参考文献：
  名称：

  Synthesis of new compounds containing the 2,3-dihydro[1,4]dioxino[2,3-b]pyridine heterocyclic system as a substructure

  摘要：

  2,3-Dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,3'-pyrrolidine (8A) and 2,3-dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,4 piperidine (9A) have been synthesized from 2-chloro-3-pyridinol. The corresponding 2,3' (8B) and 2,4' (9B) isomers were obtained via the Smiles rearrangement, while 9B was also selectively synthesized from 2-nitro-3-pyridinol. The separation of the isomers A and B under the sulfamide form was carried out by flash column chromatography.

  DOI：

  10.1016/s0040-4020(03)00513-1

文献信息

• Synthesis of new compounds containing the 2,3-dihydro[1,4]dioxino[2,3-b]pyridine heterocyclic system as a substructure
  作者：M. Soukri、S. Lazar、M.D. Pujol、M. Akssira、J.M. Leger、C. Jarry、G. Guillaumet

  DOI：10.1016/s0040-4020(03)00513-1

  日期：2003.5

  2,3-Dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,3'-pyrrolidine (8A) and 2,3-dihydro-spiro[1,4]dioxino[2,3-b]pyridine-3,4 piperidine (9A) have been synthesized from 2-chloro-3-pyridinol. The corresponding 2,3' (8B) and 2,4' (9B) isomers were obtained via the Smiles rearrangement, while 9B was also selectively synthesized from 2-nitro-3-pyridinol. The separation of the isomers A and B under the sulfamide form was carried out by flash column chromatography.