1,7-diaza-2-imino-3-aci-nitro-4,4,6-trimethylbicyclo[5.4.0]undecane | 1307949-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: 1,7-diaza-2-imino-3-aci-nitro-4,4,6-trimethylbicyclo[5.4.0]undecane
• 英文别名: N-hydroxy-7-imino-9,9,10a-trimethyl-1,2,3,4,5,10-hexahydropyrido[1,2-a][1,3]diazepin-8-imine oxide
• CAS: 1307949-31-0
• 化学式: C₁₂H₂₂N₄O₂
• 分子量: 254.332
• InChiKey: ZVTKPGKMCNEKMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  85.42
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-2-nitro-5-oxohexanenitrile 以 乙腈 为溶剂， 反应 3.0h， 生成 1,7-diaza-2-imino-3-aci-nitro-4,4,6-trimethylbicyclo[5.4.0]undecane
  参考文献：
  名称：

  Synthesis of vicinally functionalized 1,4-dihydropyridines and diazabicycles via a pseudo-intramolecular process

  摘要：

  An alpha-nitro-delta-keto nitrile readily forms the corresponding ammonium salt immediately upon treatment with an amine. When the amine liberated under equilibrium, the nucleophilic amine and the electrophilic keto nitrile come close to each other to afford so-called an intimate pair. The spatial proximity realized an efficient reaction to give a 2-amino-3-nitro-1,4-dihydropyridine; the reaction proceeded like an intramolecular reaction although it is actually an intermolecular reaction, namely the pseudo-intramolecular reaction. The bifunctionality of the keto nitrile also enabled the pseudo-intramolecular imination followed by tandem cyclization leading to diazabicyclic frameworks. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.044

文献信息

• Bicyclization involving pseudo-intramolecular imination with diamines
  作者：Nagatoshi Nishiwaki、Shotaro Hirao、Jun Sawayama、Kazuhiko Saigo、Kazuya Kobiro

  DOI：10.1039/c1cc10705d

  日期：——

  α-Nitro-δ-keto nitriles and α-nitro-δ-keto ester were readily converted to diazabicyclo compounds having vicinal functionality upon treatment with diamines. The keto nitrile attracts the diamine nearby to an acidic hydrogen to cause the pseudo-intramolecular imination which proceeds efficiently without any catalyst at room temperature.

  α-硝基-δ-酮腈和α-硝基-δ-酮酯经二胺处理后很容易转化为具有邻接官能团的二氮杂双环化合物。酮腈吸引二胺附近的酸性氢，导致伪分子内亚氨基化，这种亚氨基化在室温下无需任何催化剂即可高效进行。
• Synthesis of vicinally functionalized 1,4-dihydropyridines and diazabicycles via a pseudo-intramolecular process
  作者：Nagatoshi Nishiwaki、Shotaro Hirao、Jun Sawayama、Haruyasu Asahara、Ryuichi Sugimoto、Kazuya Kobiro、Kazuhiko Saigo

  DOI：10.1016/j.tet.2013.11.044

  日期：2014.1

  An alpha-nitro-delta-keto nitrile readily forms the corresponding ammonium salt immediately upon treatment with an amine. When the amine liberated under equilibrium, the nucleophilic amine and the electrophilic keto nitrile come close to each other to afford so-called an intimate pair. The spatial proximity realized an efficient reaction to give a 2-amino-3-nitro-1,4-dihydropyridine; the reaction proceeded like an intramolecular reaction although it is actually an intermolecular reaction, namely the pseudo-intramolecular reaction. The bifunctionality of the keto nitrile also enabled the pseudo-intramolecular imination followed by tandem cyclization leading to diazabicyclic frameworks. (C) 2013 Elsevier Ltd. All rights reserved.