exo-N-bicyclo[2.2.1]heptan-2-yl-4-methylbenzenesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: exo-N-bicyclo[2.2.1]heptan-2-yl-4-methylbenzenesulfonamide
• 英文别名: exo-N-bicyclo[2.2.1]hept-2-yl-4-methyl-benzenesulfonamide；N-(bicyclo[2.2.1]hept-2-yl)-4-methylbenzenesulfonamide；exo-N-(bicyclo[2.2.1]hept-2-yl)-p-toluenesulfonamide；N-exo-bicyclo[2,2,1]hept-2-yl-p-toluenesulfonamide；N-exo-bicyclo[2.2.1]hept-2-yl-p-toluenesulfonamide；N-bicyclo[2.2.1]hept-2-yl-p-toluenesulfonamide；N-[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]-4-methylbenzenesulfonamide
• 化学式: C₁₄H₁₉NO₂S
• 分子量: 265.376
• InChiKey: LLFRVFUBIFHUHF-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  exo-N-bicyclo[2.2.1]heptan-2-yl-4-methylbenzenesulfonamide 以71%的产率得到
  参考文献：
  名称：

  BARNETTE, W. E., J. AMER. CHEM. SOC., 1984, 106, N 2, 452-454

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Tosyl-3-aza-tricyclo(3.2.1.0^2.4-exo)octan 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 exo-N-bicyclo[2.2.1]heptan-2-yl-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Fleming, Ian; Frackenpohl, Jens; Ila, Hiriyakkanavar, Journal of the Chemical Society. Perkin transactions I, 1998, # 7, p. 1229 - 1235

  摘要：

  DOI：

文献信息

• Mechanistic Studies of the Copper-Catalyzed Electrophilic Amination of Diorganozinc Reagents and Development of a Zinc-Free Protocol
  作者：Matthew J. Campbell、Jeffrey S. Johnson

  DOI：10.1021/ol0702829

  日期：2007.4.1

  mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxylamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.

  [反应：见正文]通过遵循立体化学定义的有机金属化合物通过反应并采用环内限制性试验，可以支持SN2机制，以O-苯甲酰基-N，N-二烷基羟胺的铜催化胺化二有机锌试剂。还描述了铜催化的有机镁化合物的亲电子胺化，其中已经消除了卤化锌的使用。
• Recyclable Gallium as Catalyst Precursor for a Convenient and Solvent-Free Method for the Intermolecular Addition of Sulfonamides to Alkenes
  作者：Sven Doye、Daniel Jaspers、Raphael Kubiak

  DOI：10.1055/s-0029-1219789

  日期：2010.5

  Gallium(III) iodide, which is conveniently formed in situ from gallium and iodine, is a competent catalyst for the inter- and intramolecular addition of p-toluenesulfonamides to alkenes. After each reaction, the metallic gallium can easily be recycled and used for subsequent transformations.

  碘化镓(III)方便地由镓和碘原位形成，是一种能干的催化剂，用于对甲苯磺酰胺对烯烃的分子间和分子内加成反应。每一步反应后，金属镓可以轻松回收，并用于后续的转化。
• Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins
  作者：Junliang Zhang、Cai-Guang Yang、Chuan He

  DOI：10.1021/ja053864z

  日期：2006.2.1

  Ph3PAuOTf catalyzes efficient intra- and intermolecular hydroamination of unactivated olefins with sulfonamides.

  Ph3PAuOTf 用磺酰胺催化未活化烯烃的有效分子内和分子间加氢胺化。
• Cationic Iron-catalyzed Addition of Carboxylic Acids to Olefins
  作者：Kimihiro Komeyama、Yasuhiro Mieno、Syotaro Yukawa、Takayuki Morimoto、Ken Takaki

  DOI：10.1246/cl.2007.752

  日期：2007.6.5

  Cationic iron salts were found to be good catalysts for intra- and intermolecular addition of carboxylic acids to olefins, which afforded the corresponding esters in good yields.

  发现阳离子铁盐是羧酸与烯烃的分子内和分子间加成的良好催化剂，其以良好的产率提供相应的酯。
• 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。