N-(bicyclo[2.2.1]heptan-2-yl)-4-nitrobenzenesulfonamide

• 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-(bicyclo[2.2.1]heptan-2-yl)-4-nitrobenzenesulfonamide
• 英文别名: N-(4-nitrophenyl)bicyclo[2.2.1]heptan-2-amine；N-exo-bicyclo[2.2.1]hept-2-yl-p-nitroaniline；N-(4-nitrophenyl)bicyclo[2.2.1]hept-2-amine；(1S,2S,4R)-N-(4-nitrophenyl)bicyclo[2.2.1]heptan-2-amine
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: JVIKVOOIMKVKHS-NRUUGDAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  降冰片烯 、 4-硝基苯胺 在 silver tetrafluoroborate 、 1,2-双(二苯基膦)乙烷 、 copper(ll) bromide 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 20.0h， 以95%的产率得到N-(bicyclo[2.2.1]heptan-2-yl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  铜盐和银盐的组合催化未活化烯烃的分子间和分子内加氢胺化：Brønstedt酸催化的展开

  摘要：

  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。

  DOI：

  10.1002/adsc.201000536

文献信息

• Mechanistic Studies of the Hydroamination of Norbornene with Electrophilic Platinum Complexes: The Role of Proton Transfer
  作者：Jennifer L. McBee、Alexis T. Bell、T. Don Tilley

  DOI：10.1021/ja8030104

  日期：2008.12.10

  studies do not favor an olefin coordination mechanism but are instead consistent with a mechanism involving sulfonamide coordination and generation of an acidic proton that is transferred to the norbornene. It is postulated that the resulting norbornyl cation is then attacked by free sulfonamide, and loss of proton from this adduct completes the hydroamination. The platinum-sulfonamide complex readily

  使用 L2Pt(OTf)2 (L2 = (t)Bu2bpy, (t)BuC6H4N== C(CH3)C( CH3)==NC6H4(t)Bu、(C6H5)2PCH2CH2P(C6H5)2、(C6F5)2PCH2CH2P(C6F5)2、S​​-BINAP)。伪一级动力学表明反应速率几乎不依赖于辅助配体。机理研究不支持烯烃配位机制，而是与涉及磺酰胺配位和产生转移到降冰片烯的酸性质子的机制一致。据推测，所得降冰片基阳离子随后被游离磺酰胺攻击，并且从该加合物中损失质子完成加氢胺化。铂-磺酰胺络合物很容易发生去质子化，得到从反应溶液中分离出来的μ-酰氨基铂桥二聚体。这些研究还涉及使用 Me3SiPh 和 Me3SnPh 作为非亲核质子陷阱。Ph-E 键的断裂用于检测酸性催化活性物质。
• 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。
• 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。
• Highly Efficient and Reusable Ionic Liquids for the Catalyzed Hydro­amination of Alkenes with Sulfonamides, Carbamates, and Carboxamides
  作者：Li-Wen Xu、Chun-Gu Xia、Lei Yang

  DOI：10.1055/s-0029-1216825

  日期：2009.6

  SO3H-Functionalized ionic liquids were found to be efficient and reusable catalysts in the hydroamination of sulfonamides, carboxamides, p-nitroaniline and carbamates with nonactivated alkenes. The hydroamination could be performed on a large scale and the acidic ionic liquid catalyst could be reused successfully.

  研究发现，在磺酰胺、羧酰胺、对硝基苯胺和氨基甲酸酯与非活化烯烃的加氢反应中，SO3H 官能化离子液体是高效且可重复使用的催化剂。氢化反应可大规模进行，酸性离子液体催化剂可成功重复使用。
• 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。