N-exo-bicyclo[2.2.1]hept-2-yl-aniline | 22611-62-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-exo-bicyclo[2.2.1]hept-2-yl-aniline
• 英文别名: N-phenylbicyclo[2.2.1]heptan-2-amine；N-phenylbicyclo[2.2.1]hept-2-amine；exo-2-(phenylamino)norbornane；exo-2-phenylaminonorbornane；(1S,2S,4R)-N-phenylbicyclo[2.2.1]heptan-2-amine
• CAS: 22611-62-7；40649-30-7；15995-50-3
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: SFCLMYIWOIJNAD-MDZLAQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-exo-bicyclo[2.2.1]hept-2-yl-aniline 、 对甲苯磺酰氯 在 吡啶 作用下， 以311 mg的产率得到N-(exo-bicyclo[2.2.1]hept-2-yl)-4-methyl-N-phenyl-benzenesulfonamide
  参考文献：
  名称：

  TiCl₄-Catalyzed Intermolecular Hydroamination Reactions of Norbornene

  摘要：

  An intermolecular hydroamination reaction of norbornene is presented that uses catalytic amounts of user-friendly TiCl4 and tolerates a variety of functional groups. In addition, a secondary amine is converted using this methodology.

  DOI：

  10.1021/ol049282o
• 作为产物：
  描述：

  降莰烷 、 硝基苯 在 air 、 过氧化二异丙苯 作用下， 反应 16.0h， 以58%的产率得到N-exo-bicyclo[2.2.1]hept-2-yl-aniline
  参考文献：
  名称：

  过氧化氢介导的环戊烷与硝基芳烃的胺化反应

  摘要：

  Abstractmagnified imageA direct amination of simple cycloalkanes with nitroarenes mediated by peroxides has been discovered. Various secondary arylamines were obtained efficiently from cycloalkanes. The reaction tolerates a wide range of functionalities as well as aqueous conditions. No metal was required for this novel amination reaction.

  DOI：

  10.1002/adsc.200800689

文献信息

• Intermolecular hydroamination and hydroarylation reactions of alkenes in ionic liquids
  作者：Alexandre A.M. Lapis、Brenno A. DaSilveira Neto、Jackson D. Scholten、Fabiane M. Nachtigall、Marcos N. Eberlin、Jairton Dupont

  DOI：10.1016/j.tetlet.2006.07.073

  日期：2006.9

  hydroamination or hydroarylation reactions of norbornene and cyclohexadiene performed with catalytic amounts of Brönsted or Lewis acid in ionic liquids were found to provide higher selectivity and yields than those performed in classical organic solvents. The ionic liquid increases the acidity of the media and stabilizes ionic intermediates through the formation of supramolecular aggregates.

  发现在离子液体中用催化量的布朗斯台德酸或路易斯酸进行的降冰片烯和环己二烯的分子间加氢胺化或加氢芳基化反应比传统的有机溶剂具有更高的选择性和产率。离子液体通过形成超分子聚集体来增加介质的酸度并稳定离子中间体。
• HI-Catalyzed Hydroamination and Hydroarylation of Alkenes
  作者：Sven Doye、Klaudia Marcseková

  DOI：10.1055/s-2006-958934

  日期：2007.1

  Aromatic amines react with alkenes in the presence of catalytic amounts of aqueous HI to give mixtures of the corresponding hydroamination and hydroarylation products. While the hydroamination reaction is the preferred pathway for aliphatic alkenes, the hydroarylation reaction becomes more important when styrenes are used as substrates. In general, the electronic properties of the alkene and the amine strongly influence the efficiency and the selectivity of the reaction.

  芳香胺在催化量的水合碘酸存在下与烯烃反应，生成相应的氢胺化和氢芳烃化产品的混合物。对于脂肪族烯烃，氢胺化反应是优选路径，而当使用苯乙烯作为底物时，氢芳烃化反应变得更加重要。一般来说，烯烃和胺的电子特性强烈影响反应的效率和选择性。
• Inter- and Intramolecular Hydroamination of Unactivated Alkenes Catalysed by a Combination of Copper and Silver Salts: The Unveiling of a Brønstedt Acid Catalysis
  作者：Christophe Michon、Florian Medina、Frédéric Capet、Pascal Roussel、Francine Agbossou-Niedercorn

  DOI：10.1002/adsc.201000536

  日期：2010.12.17

  The combined use of a copper halide, a silver salt and a phosphane ligand was applied for the catalysis of inter- and intramolecular hydroamination of alkenes. The reactions of unactivated olefins with nitrogen substrates were investigated. Mechanistic investigations demonstrated that the catalytic system generated a Brønsted acid which appeared to be the prominent catalytic species.

  卤化铜，银盐和膦配体的组合使用被用于催化烯烃的分子间和分子内加氢胺化。研究了未活化烯烃与氮底物的反应。机理研究表明，该催化体系产生了布朗斯台德酸，该酸似乎是主要的催化物种。
• Efficient C−N Bond Formations Catalyzed by a Proton-Exchanged Montmorillonite as a Heterogeneous Brønsted Acid
  作者：Ken Motokura、Nobuaki Nakagiri、Kohsuke Mori、Tomoo Mizugaki、Kohki Ebitani、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.1021/ol0619821

  日期：2006.9.1

  addition of sulfonamides and carboxamides to simple alkenes proceeded smoothly using a proton-exchanged montmorillonite catalyst. The spent catalyst was recovered easily from the reaction mixture and was reusable at least five times without any loss of activity. The unique acidity of the proton-exchanged montmorillonite (H-mont) catalyst was found to be applicable to additional reactions: substitution of hydroxyl

  使用质子交换的蒙脱石催化剂，可以将磺酰胺和羧酰胺亲核加成到简单的烯烃中。废催化剂很容易从反应混合物中回收，并且可以重复使用至少五次而没有任何活性损失。发现质子交换的蒙脱石（H-mont）催化剂的独特酸度适用于其他反应：用酰胺和苯胺取代醇的羟基。
• Unexpected catalytic and stereoselective hydroarylation of norbornene during the attempted rhodium-catalysed hydroamination of norbornene with aniline or diphenylamine
  作者：Jean-Jacques Brunet、Denis Neibecker、Karine Philippot

  DOI：10.1039/c39920001215

  日期：——

  The reaction of aniline (or diphenylamine) with norbornene in the presence of a catalytic system generated from [Rh(PEt3)2Cl}2] and PhNHLi (or Ph2NLi) results in hydroarylation to yield 2-(2-aminophenyl)norbornane [or 2-(2-phenylaminophenyl)norbornane].

  苯胺（或二苯胺）与降冰片烯在 [Rh(PEt3)2Cl}2] 和 PhNHLi（或 Ph2NLi）生成的催化体系存在下反应，导致加氢芳基化，生成 2-(2-氨基苯基)降冰片烷 [或2-(2-苯基氨基苯基)降冰片烷]。