N-benzylidene-β-(2-bromo-4,5-dimethoxyphenyl)ethylamin | 75767-96-3

• 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-benzylidene-β-(2-bromo-4,5-dimethoxyphenyl)ethylamin
• 英文别名: (E)-N-[2-(2-Bromo-4,5-dimethoxyphenyl)ethyl]-1-phenylmethanimine；N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]-1-phenylmethanimine
• CAS: 75767-96-3
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: ISNYRNSLLCNVTK-UHFFFAOYSA-N

物化性质

• 沸点：
  205-207 °C(Press: 0.5 Torr)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzylidene-β-(2-bromo-4,5-dimethoxyphenyl)ethylamin 在 sodium tetrahydroborate 作用下， 生成 N-benzyl-2-bromo-4,5-dimethoxyphenethylamine
  参考文献：
  名称：

  在 K2CO3 存在下，Pd(OAc)2 和 Cu(OAc)2 的无磷 Pd0 催化环氨基化和羰基化：苯并环胺和苯内酰胺的制备

  摘要：

  研究了无磷 Pd0 催化的分子内芳香胺化。发现邻卤苯乙胺和 3-(邻卤苯基)丙胺在基于 Pd(OAc)2 和 Cu(OAc)2 的催化体系中在 K2CO3 存在下转化为二氢吲哚和喹啉。该方法在含有异喹啉环的底物上的应用——1-(邻溴苄基)-3,4-二氢异喹啉 6、1-(邻溴苄基)-1,2,3,4-四氢异喹啉 7 和 1- (o-溴苯乙基)异喹啉 9 – 提供吲哚[2,1-a]异喹啉和二苯并[a,f]喹嗪环系统 8 和 10。将方法扩展到 β-咔啉（化合物 11、12 和 17）生产了苯并[f]吲哚[2,3-a]吲哚并13-ones 15和苯并[f]吲哚[2,3-a]喹啉18。苯并[f]吡啶并[3,4-a]吲哚嗪和吲哚并[f]吡啶并[3，4-a]indolizin-12-one 环系统 27 和 31 以类似的方式构建。还发现在 CO 气氛下，相同的催化体系产生了相应的苯内酰胺、异喹诺[2,1-a][2

  DOI：

  10.1002/ejoc.201101214
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 N-benzylidene-β-(2-bromo-4,5-dimethoxyphenyl)ethylamin
  参考文献：
  名称：

  在 K2CO3 存在下，Pd(OAc)2 和 Cu(OAc)2 的无磷 Pd0 催化环氨基化和羰基化：苯并环胺和苯内酰胺的制备

  摘要：

  研究了无磷 Pd0 催化的分子内芳香胺化。发现邻卤苯乙胺和 3-(邻卤苯基)丙胺在基于 Pd(OAc)2 和 Cu(OAc)2 的催化体系中在 K2CO3 存在下转化为二氢吲哚和喹啉。该方法在含有异喹啉环的底物上的应用——1-(邻溴苄基)-3,4-二氢异喹啉 6、1-(邻溴苄基)-1,2,3,4-四氢异喹啉 7 和 1- (o-溴苯乙基)异喹啉 9 – 提供吲哚[2,1-a]异喹啉和二苯并[a,f]喹嗪环系统 8 和 10。将方法扩展到 β-咔啉（化合物 11、12 和 17）生产了苯并[f]吲哚[2,3-a]吲哚并13-ones 15和苯并[f]吲哚[2,3-a]喹啉18。苯并[f]吡啶并[3,4-a]吲哚嗪和吲哚并[f]吡啶并[3，4-a]indolizin-12-one 环系统 27 和 31 以类似的方式构建。还发现在 CO 气氛下，相同的催化体系产生了相应的苯内酰胺、异喹诺[2,1-a][2

  DOI：

  10.1002/ejoc.201101214

文献信息

• Stereoselective synthesis of benzoquinolizidines and related homologues via intramolecular addition to dihydropyridones
  作者：Piotr Szcześniak、Artur Ulikowski、Olga Staszewska-Krajewska、Grzegorz Lipner、Bartłomiej Furman

  DOI：10.1016/j.tet.2016.04.022

  日期：2016.6

  An efficient method for the synthesis of benzoquinolizidine and benzoindolizidine alkaloid scaffolds is described. The synthetic strategy is based on the lithium–halogen exchange-initiated intramolecular conjugate addition of aryllithiums to 2,3-dihydro-4-pyridones. A similar cyclization was also carried out under free radical conditions providing the expected cyclic compounds, although with significantly

  描述了一种合成苯并喹喔啉和苯并吲哚并核生物碱支架的有效方法。合成策略基于将锂-卤素交换引发的芳基锂分子内共轭加成到2,3-二氢-4-吡啶酮中。在自由基条件下也进行了类似的环化反应，提供了预期的环状化合物，尽管收率明显降低。研究了链长和受体取代方式对环构建可行性的影响。
• Fidalgo, Jesus; Castedo, Luis; Dominguez, Domingo, Heterocycles, 1994, vol. 39, # 2, p. 581 - 590
  作者：Fidalgo, Jesus、Castedo, Luis、Dominguez, Domingo

  DOI：——

  日期：——
• Three-Step Access to the Tricyclic Benzo[<i>a</i>]quinolizine Ring System
  作者：Stephan Kirschbaum、Herbert Waldmann

  DOI：10.1021/jo972035w

  日期：1998.7.1

  Access to the tricyclic benzo[a]quinolizine ring system, which forms the characteristic framework of alkaloids of the berberine and emetine type, is readily obtained by a three-step reaction sequence. This sequence includes the formation of a Schiff base, derived from a 2-bromo-substituted phenylethylamine, and its tandem Mannich/conjugate addition reaction with an electron-rich silyloxy diene forming an intermediate enaminone, which subsequently undergoes a Heck-type cyclization. Highest yields of the tandem Mannich/conjugate addition for aromatic Schiff bases and formaldehyde imines are observed in the presence of ZnCl2 in THF, whereas aromatic imines give the best results in the presence of EtAlCl2 in CH2Cl2. The best results for the Heck-type cyclizations are obtained either under heterogeneous conditions in the presence of K2CO3/NEt4Cl at 120 degrees C in DMF or in refluxing toluene or under homogeneous conditions at 100 degrees C in DMF in the presence of NEt-(i-Pr)(2). Depending on the substitution pattern of the diene and the steric demand of the base employed in the Heck cyclization, benzo[a]quinolizines carrying a double bond in the 11b,1- or 3,4-position or in an exocyclic position are obtained with fair to good results. A mechanistic rationale for this behavior is proposed. If chiral amines, e.g., derived from an amino acid ester, are employed in the three-step reaction sequence, chiral tricyclic benzo[a]quinolizines become accessible in a straightforward manner.
• Schiff bases as external and internal electrophiles in reactions of functionalized organolithium reagents. A new route to isoindoline derivatives and 1,2,3,4-tetrahydroisoquinolines
  作者：Charles K. Bradsher、David A. Hunt

  DOI：10.1021/jo00315a021

  日期：1981.1
• Indoline Formation by Regioselective Aryl Radical Cyclization to Azomethine Bond
  作者：Seiichi Takano、Mahito Suzuki、Kunio Ogasawara

  DOI：10.3987/com-93-s7

  日期：——

  Aryl radical-initiated cyclization of the ketimines derived from acetophenone and benzophenone occurred exclusively at the nitrogen end of the azomethine bond in an exo-5 mode to yield the corresponding indoline derivatives.