exo-N-bicyclo[2.2.1]hept-2-yl-benzenesulfonamide

• 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: exo-N-bicyclo[2.2.1]hept-2-yl-benzenesulfonamide
• 英文别名: N-[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]benzenesulfonamide
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: WRYRNMGIJJDXSS-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯磺酰胺 、 norbornene 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.67h， 以93%的产率得到exo-N-bicyclo[2.2.1]hept-2-yl-benzenesulfonamide
  参考文献：
  名称：

  在热和微波辅助条件下，膦金（I）催化的烯烃加氢胺化。

  摘要：

  [反应：见正文]在热和微波辅助条件下，膦金（I）络合物催化末端烯烃的异构化和未活化烯烃的加氢胺化。这是将微波辐射用作金（I）催化的有机反应的热源的第一个示例。

  DOI：

  10.1021/ol060719x

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。
• The hydroamination of alkenes with sulfonamides catalyzed by the recyclable silica gel supported triflic acid
  作者：Pei Nian Liu、Fei Xia、Zheng Le Zhao、Qing Wei Wang、Yu Jie Ren

  DOI：10.1016/j.tetlet.2011.09.025

  日期：2011.11

  The vast applications of triflic acid (TfOH) in catalysis are severely limited by its corrosive and fuming properties. Immobilization of TfOH on silica gel well solves these problems and affords efficient recovery and reusability of TfOH. Two types of supported TfOH, the prepared silica gel supported TfOH and the in situ silica gel adsorbed TfOH, both exhibit good catalytic activity and reusability in the hydroamination of alkene with sulfonamide. The in situ silica gel adsorbed catalyst has been used for 5 runs with maintained reactivities and yields, which are superior to the performance of the prepared silica gel supported TfOH. For a series of alkenes and various sulfonamides, the heterogeneous hydroamination reactions catalyzed by both types of silica gel supported TfOH to afford similar moderate to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Heteropoly acids: a green and efficient heterogeneous Brønsted acidic catalyst for the intermolecular hydroamination of olefins
  作者：Lei Yang、Li-Wen Xu、Chun-Gu Xia

  DOI：10.1016/j.tetlet.2008.03.034

  日期：2008.4

  Intermolecular hydroamination of non-activated olefins with amides and benzyl carbamate proceeds efficiently in the presence of environmentally benign silicotungstic acid (HSiW) catalyst under mild conditions in air to afford addition products in good to excellent yields. (c) 2008 Elsevier Ltd. All rights reserved.
• Phosphine Gold(I)-Catalyzed Hydroamination of Alkenes under Thermal and Microwave-Assisted Conditions
  作者：Xin-Yuan Liu、Cheng-Hui Li、Chi-Ming Che

  DOI：10.1021/ol060719x

  日期：2006.6.1

  [reaction: see text] Phosphine gold(I) complexes catalyzed isomerization of terminal alkenes and hydroamination of unactivated alkenes under thermal and microwave-assisted conditions. This is the first example of the use of microwave radiation as a heat source for gold(I)-catalyzed organic reactions.

  [反应：见正文]在热和微波辅助条件下，膦金（I）络合物催化末端烯烃的异构化和未活化烯烃的加氢胺化。这是将微波辐射用作金（I）催化的有机反应的热源的第一个示例。