2-benzylamino-1,4-dihydro-3-nitro-4,4,6-trimethylpyridine | 1186339-70-7

• 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-benzylamino-1,4-dihydro-3-nitro-4,4,6-trimethylpyridine
• 英文别名: 2-benzylamino-1,4-dihydro-4,4,6-trimethyl-3-nitropyridine；N-benzyl-4,4,6-trimethyl-3-nitro-1H-pyridin-2-amine
• CAS: 1186339-70-7
• 化学式: C₁₅H₁₉N₃O₂
• 分子量: 273.335
• InChiKey: XZGPWOXXUNWWPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-2-nitro-5-oxohexanenitrile 、 苄胺 以 乙腈 为溶剂， 反应 40.0h， 以80%的产率得到2-benzylamino-1,4-dihydro-3-nitro-4,4,6-trimethylpyridine
  参考文献：
  名称：

  Pseudo-intramolecular Cyclization of α-Nitro-δ-keto Nitrile Leading to 2-Amino-3-nitro-1,4-dihydropyridines

  摘要：

  一种新概念--假分子内过程--被应用于多官能化杂环化合物的合成。酸性 α-硝基-δ-酮腈在与胺处理后很容易形成铵盐。当胺在平衡状态下释放出来时，亲核胺和亲电酮腈就形成了亲密的一对，从而使胺有效地攻击酮腈的氰基。随后的环化反应产生了部分结构的 1,4-二氢吡啶，其邻接位置含有一个氨基和一个硝基。

  DOI：

  10.1246/cl.2009.680

文献信息

• Pseudo-intramolecular Cyclization of α-Nitro-δ-keto Nitrile Leading to 2-Amino-3-nitro-1,4-dihydropyridines
  作者：Nagatoshi Nishiwaki、Kengo Kakutani、Mina Tamura、Masahiro Ariga

  DOI：10.1246/cl.2009.680

  日期：2009.7.5

  A novel concept—the pseudo-intramolecular process—is applied to the synthesis of multiply functionalized heterocyclic compounds. Acidic α-nitro-δ-keto nitrile easily forms an ammonium salt upon treatment with an amine. When the amine is liberated under equilibrium, an intimate pair, namely, a nucleophilic amine and an electrophilic keto nitrile are located close to each other, is formed; thus the amine efficiently attacks a cyano group of keto nitrile. As a result of subsequent cyclization, 1,4-dihydropyridines containing an amino and a nitro group at the vicinal positions as a partial structure are afforded.

  一种新概念--假分子内过程--被应用于多官能化杂环化合物的合成。酸性 α-硝基-δ-酮腈在与胺处理后很容易形成铵盐。当胺在平衡状态下释放出来时，亲核胺和亲电酮腈就形成了亲密的一对，从而使胺有效地攻击酮腈的氰基。随后的环化反应产生了部分结构的 1,4-二氢吡啶，其邻接位置含有一个氨基和一个硝基。
• 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.