N-allyl-N-benzyl-2-bromoaniline | 133931-11-0

• 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: N-allyl-N-benzyl-2-bromoaniline
• 英文别名: N-benzyl-2-bromo-N-prop-2-enylaniline
• CAS: 133931-11-0
• 化学式: C₁₆H₁₆BrN
• 分子量: 302.214
• InChiKey: JDHKKJAVYVPTHW-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±42.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-N-benzyl-2-bromoaniline 在 zirconocene methyl chloride 、 碘 、 叔丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 生成 1-benzyl-4-iodo-3-methyleneindoline
  参考文献：
  名称：

  Tidwell, Jeffrey H.; Senn, Dwayne R.; Buchwald, Stephen L., Journal of the American Chemical Society, 1991, vol. 113, # 12, p. 4685 - 4686

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄基-2-溴苯胺 、 3-溴丙烯 在 正丁基锂 作用下， 生成 N-allyl-N-benzyl-2-bromoaniline
  参考文献：
  名称：

  Synthesis of Polysubstituted Indoles and Indolines by Means of Zirconocene-Stabilized Benzyne Complexes

  摘要：

  The development of a new method for the regiospecific synthesis of polysubstituted indoles and indolines is reported. The key steps involve the generation of zirconocene-stabilized benzyne complexes and subsequent intramolecular olefin insertion reactions to provide tricyclic indoline zirconacycles. The zirconacyclic intermediates were cleaved with iodine to yield diiodo indolines, which were converted to a wide variety of indole and indoline products, such as analogs of tryptamine, serotonin, tryptophan, and the pharmacophore of CC-1065.

  DOI：

  10.1021/ja00105a021

文献信息

• One-Pot Procedure for the Synthesis of 1,5-Benzodiazepines from<i>N</i>-Allyl-2-bromoanilines
  作者：Marco Weers、Lars H. Lühning、Vanessa Lührs、Christian Brahms、Sven Doye

  DOI：10.1002/chem.201604561

  日期：2017.1.26

  to pharmacologically relevant 1,5‐benzodiazepines. The process takes advantage of the excellent regioselectivity of the initial hydroaminoalkylation performed in the presence of a titanium mono(formamidinate) catalyst and the fact that the exclusively formed branched hydroaminoalkylation products can only undergo palladium‐catalyzed cyclization to 1,5‐benzodiazepines.

  一种新的一锅法，其中包括将钛催化的N-烯丙基-2-溴苯胺的分子间氢氨基烷基化与N-甲基苯胺的作用以及随后的分子内Buchwald-Hartwig胺化作用可直接获得与药理相关的1,5-苯并二氮杂s。该方法利用了在单（甲酰胺基）钛催化剂存在下进行的初始加氢氨基烷基化反应的优异区域选择性以及仅形成的支链加氢氨基烷基化产物只能经历钯催化环化成1,5-苯并二氮杂fact的事实。
• Nitrogen Assistance in Intramolecular Nickel-Promoted Tandem Cyclization−Quenching Processes
  作者：Daniel Solé、Yolanda Cancho、Amadeu Llebaria、Josep M. Moretó、Antonio Delgado

  DOI：10.1021/jo960677y

  日期：1996.1.1

  A diastereoselective and mild cyclization-quenching process based on the treatment of nitrogen-tethered halodienes with stoichiometric Ni(COD)(2) is described. The success of this methodology relies on the presence of a distal amino group capable of coordinating with the metal in the transient vinyl or alkylnickel species, thus controlling the diastereoselectivity of the cyclization step and preventing Ni-H beta-elimination prior to the quenching, In general, better results are obtained in cyclizations taking place via a 5-exo-trig process, and a diversity of mono- and bicyclic nitrogenated systems are afforded in high yields by the proper choice of starting halodienes and quenching reagents, The presence of 2,2'-bipyridine as a ligand results in an acceleration of the process, and in some cases, higher diastereoselectivities and/or supression of the Ni-H beta-elimination are observed.
• Enantioselective Synthesis of 3-Substituted Indolines by Asymmetric Intramolecular Carbolithiation in the Presence of (−)-Sparteine
  作者：Gema Sanz Gil、Ulrich M. Groth

  DOI：10.1021/ja0012164

  日期：2000.7.1