2-(allyl(methyl)amino)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-(allyl(methyl)amino)nicotinaldehyde
• 英文别名: 2-[Allyl(methyl)amino]nicotinaldehyde；2-[methyl(prop-2-enyl)amino]pyridine-3-carbaldehyde
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: AGKDBXNILXUIMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-(allyl(methyl)amino)nicotinaldehyde 在 氰基硼氘化钠 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 0.17h， 生成 3-(5-deutero-1-methylpyrrolidin-2-yl)-N-methylpyridin-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-吡啶甲醇 在 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-(allyl(methyl)amino)nicotinaldehyde
  参考文献：
  名称：

  通过分子内的1,3-偶极环加成反应合成1,8-萘啶-5-酮衍生物

  摘要：

  1,8-萘啶-5-酮衍生物[（5,6,7,8-四氢-（3-氯-6-羟甲基-8-甲基）-1,8-萘啶-5-酮（9 ） ]从2-氯烟酸开始，以分子内的1,3-偶极环加成反应为关键步骤进行了描述。

  DOI：

  10.1002/jhet.5570320531

文献信息

• Intramolecular Cycloaddition of Azomethine Ylides Activated by Aromatic Rings: Scope and Limitations
  作者：Hongxiang Xie、Bowen Gong、Xinran Zhong、Hongming Cui、Jinbao Xiang

  DOI：10.1007/s10593-016-1912-9

  日期：2016.7

  Simple aromatic substituents in the substrate molecule, including pyrimidine, pyridine, and benzene rings, directly facilitated the intramolecular cycloaddition of azomethine ylide to alkene. All of these aromatic substituents aided the formation of azomethine ylides, which then underwent highly diastereospecific sequential cycloaddition. It was shown that both the presence of an electron-deficient

  底物分子中的简单芳香族取代基（包括嘧啶，吡啶和苯环）直接促进了亚甲亚胺叶立德分子内环加成烯烃。所有这些芳族取代基均有助于形成甲亚胺基团，然后对其进行高度非对映特异性的连续环加成。结果表明，缺电子的芳环和在芳环相对于氨基甲基的邻位的取代基的存在都增强了偶氮甲亚胺对环加成的反应性。
• Synthesis of a 1,8-naphthyridin-5-one derivative<i>via</i>an intramolecular 1,3-dipolar cycloaddition reaction
  作者：Mark W. Read、Partha S. Ray

  DOI：10.1002/jhet.5570320531

  日期：1995.9

  Synthesis of a 1,8-naphthyridin-5-one derivative [(5,6,7,8-tetrahydro-(3-chloro-6-hydroxymethyl-8-methyl)-1,8-naphthyridin-5-one (9)] is described starting from 2-chloronicotinic acid using an intramolecular 1,3-dipolar cycloaddition reaction as the key step.

  1,8-萘啶-5-酮衍生物[（5,6,7,8-四氢-（3-氯-6-羟甲基-8-甲基）-1,8-萘啶-5-酮（9 ） ]从2-氯烟酸开始，以分子内的1,3-偶极环加成反应为关键步骤进行了描述。
• 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.