9-nitrojulolidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-nitrojulolidine
• 英文别名: 7-Nitrojulolidin；9-Nitrojulolidin；9-nitro-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline；9-Nitro-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline；7-nitro-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: BMDCDJCEUIDQDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-硝基-1,2,3,4-四氢喹啉 在 SbF₅#HF 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 96.25h， 生成 9-nitrojulolidine
  参考文献：
  名称：

  Selective Anti-Markovnikov Cyclization and Hydrofluorination Reaction in Superacid HF/SbF₅: A Tool in the Design of Nitrogen-Containing (Fluorinated) Polycyclic Systems

  摘要：

  The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.

  DOI：

  10.1021/jo400398y

文献信息

• Mono-nitration of aromatic compounds via their nitric acid salts
  作者：Pingsheng Zhang、Miall Cedilote、Thomas P. Cleary、Michael E. Pierce

  DOI：10.1016/j.tetlet.2007.10.027

  日期：2007.12

  Aromatic compounds bearing a basic nitrogen atom can be converted to the corresponding nitric acid salts. Mono-nitration of the compounds can be carried out by adding a dichloromethane solution of the salts to sulfuric acid, or by adding acetyl chloride (or trifluoroacetic anhydride) to a dichloromethane solution of the salts. This protocol provides, among other benefits, the most convenient and reliable

  带有碱性氮原子的芳族化合物可以转化为相应的硝酸盐。化合物的单硝化反应可以通过将盐的二氯甲烷溶液添加到硫酸中，或将乙酰氯（或三氟乙酸酐）添加到盐的二氯甲烷溶液中来进行。除其他优点外，该协议还提供了最方便，最可靠的方式来防止硝化过度/欠燃，尤其适用于规模放大。
• Mono-nitration of aromatic compounds via nitrate salts
  申请人：Cedilote Miall

  公开号：US20070255057A1

  公开（公告）日：2007-11-01

  A method of nitrating a compound selected from the group consisting of is provided.

  提供了一种从所选化合物中硝化的方法。
• US7429589B2
  申请人：——

  公开号：US7429589B2

  公开（公告）日：2008-09-30
• Selective Anti-Markovnikov Cyclization and Hydrofluorination Reaction in Superacid HF/SbF₅: A Tool in the Design of Nitrogen-Containing (Fluorinated) Polycyclic Systems
  作者：Guillaume Compain、Céline Bonneau、Agnès Martin-Mingot、Sébastien Thibaudeau

  DOI：10.1021/jo400398y

  日期：2013.5.3

  The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.