2-(diallylamino)nicotinaldehyde

• 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-(diallylamino)nicotinaldehyde
• 英文别名: 2-[Bis(prop-2-enyl)amino]pyridine-3-carbaldehyde；2-[bis(prop-2-enyl)amino]pyridine-3-carbaldehyde
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: PXUJWJMFGMSNEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(diallylamino)nicotinaldehyde 在 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 0.17h， 生成 N-allyl-3-(1-benzylpyrrolidin-2-yl)pyridin-2-amine
  参考文献：
  名称：

  Substituent-directed reduction of cyclic aminals leading to two different heterocycles selectively: syntheses of functionalized nicotines and pyrido[2,3-b]azepines

  摘要：

  A new strategy of substituent-directed reductive ring-opening of aza-bridged pyridoazepine systems was designed and developed. The direction of the ring-opening is determined by the electron negativity of substituents attached to the nitrogen atoms. A plausible mechanism involving iminiums as the key intermediates to the two reaction pathways was proposed. The reductive cleavage reaction provides a convenient method to access novel 2-aminonicotine and pyrido[2,3-b]azepine derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.025
• 作为产物：
  描述：

  2-氯-3-吡啶甲醛 、 二烯丙基胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以57%的产率得到2-(diallylamino)nicotinaldehyde
  参考文献：
  名称：

  Substituent-directed reduction of cyclic aminals leading to two different heterocycles selectively: syntheses of functionalized nicotines and pyrido[2,3-b]azepines

  摘要：

  A new strategy of substituent-directed reductive ring-opening of aza-bridged pyridoazepine systems was designed and developed. The direction of the ring-opening is determined by the electron negativity of substituents attached to the nitrogen atoms. A plausible mechanism involving iminiums as the key intermediates to the two reaction pathways was proposed. The reductive cleavage reaction provides a convenient method to access novel 2-aminonicotine and pyrido[2,3-b]azepine derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.025

文献信息

• Substituent-directed reduction of cyclic aminals leading to two different heterocycles selectively: syntheses of functionalized nicotines and pyrido[2,3-b]azepines
  作者：Yuewei Zhang、Lianyou Zheng、Fengzhi Yang、Zhuoqi Zhang、Qun Dang、Xu Bai

  DOI：10.1016/j.tet.2015.02.025

  日期：2015.4

  A new strategy of substituent-directed reductive ring-opening of aza-bridged pyridoazepine systems was designed and developed. The direction of the ring-opening is determined by the electron negativity of substituents attached to the nitrogen atoms. A plausible mechanism involving iminiums as the key intermediates to the two reaction pathways was proposed. The reductive cleavage reaction provides a convenient method to access novel 2-aminonicotine and pyrido[2,3-b]azepine derivatives. (C) 2015 Elsevier Ltd. All rights reserved.