(E)-N-Benzyl-1-(2-bromo-4,5-dimethoxyphenyl)methanimine | 89525-46-2

• 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: (E)-N-Benzyl-1-(2-bromo-4,5-dimethoxyphenyl)methanimine
• 英文别名: N-benzyl-1-(2-bromo-4,5-dimethoxyphenyl)methanimine
• CAS: 89525-46-2
• 化学式: C₁₆H₁₆BrNO₂
• 分子量: 334.213
• InChiKey: HJBGIHVEAAXFLO-UHFFFAOYSA-N

物化性质

• 沸点：
  420.0±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (E)-N-Benzyl-1-(2-bromo-4,5-dimethoxyphenyl)methanimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 1-bromo-2-benzylaminomethyl-4,5-dimethoxybenzene
  参考文献：
  名称：

  钯介导的 β-氨基酯的分子内 Buchwald-Hartwig α-芳基化：功能化四氢异喹啉的合成

  摘要：

  描述了基于 β-氨基酯的分子内 Buchwald-Hartwig α-芳基化合成功能化 1,2,3,4-四氢异喹啉的简洁有效的三步策略。所提出的合成在操作上很简单，并且适合合成许多类似物。

  DOI：

  10.1055/s-0030-1260934
• 作为产物：
  描述：

  6-溴藜芦醛 、 苄胺 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (E)-N-Benzyl-1-(2-bromo-4,5-dimethoxyphenyl)methanimine
  参考文献：
  名称：

  钯介导的 β-氨基酯的分子内 Buchwald-Hartwig α-芳基化：功能化四氢异喹啉的合成

  摘要：

  描述了基于 β-氨基酯的分子内 Buchwald-Hartwig α-芳基化合成功能化 1,2,3,4-四氢异喹啉的简洁有效的三步策略。所提出的合成在操作上很简单，并且适合合成许多类似物。

  DOI：

  10.1055/s-0030-1260934

文献信息

• Modular Strategy for the Synthesis of Functionalized Aryl-Fused Azabicyclo[2.2.2]octanes via Sequential Cu/Pd/Ru Catalysis
  作者：Lucas F. McCormick、Helena C. Malinakova

  DOI：10.1021/jo400974k

  日期：2013.9.6

  novel sequence of Cu-catalyzed three-component coupling of diversely substituted N-benzyl o-bromoaryl imines with methacryloyl chloride and vinyltributyl stannane followed by Pd-catalyzed Heck annulation. Subsequent diversification of the aryl-fused 2-azabicyclo[2.2.2]octane core was achieved by attaching a flexible linker and a potential second pharmacophore via Ru-catalyzed cross-metathesis and a

  芳基稠合的2-氮杂双环[2.2.2]辛烷是通过Cu催化的新序列，将不同取代的N-苄基邻溴代亚芳基亚胺与甲基丙烯酰氯和乙烯基三丁基锡锡烷进行Cu催化的三组分偶联，然后进行Pd催化的Heck环化。芳基稠合的2-氮杂双环[2.2.2]辛烷核的随后多样化是通过Ru催化的交叉复分解和亲核取代连接柔性接头和潜在的第二药效团实现的。
• Palladium assisted organic reactions
  作者：P.W. Clark、S.F. Dyke

  DOI：10.1016/0022-328x(84)80664-6

  日期：1984.11

  A new, improved method is described for the preparation of cyclopalladated benzalimines; it consists of reacting the ortho-bromobenzalimine with bis(dibenzylideneacetone) palladium(0). A number of substituted o-bromobenzalimines has been studied; the bridged bromide dimers and the corresponding bromo (N-substituted benzalimine-6,C,N)triphenylphosphinepalladium(II) complexes have been fully characterised

  描述了一种新的，改进的方法，用于制备环palpalated苯扎利明; 它由邻-溴苯甲酰亚胺与双（二亚苄基丙酮）钯（0）​​反应组成。已经研究了许多取代的邻溴苯甲酰亚胺。桥联的溴化物二聚体和相应的溴（N-取代的苯扎利明-6，C，N）三苯基膦钯（II）配合物已得到充分表征，并记录了1 H和13 C NMR光谱数据。在研究的N-苯基苯甲酰亚胺的情况下，还分离并鉴定了双（三苯基膦）配合物。
• Cyclopalladated primary, secondary and tertiary benzylamines, and benzalimines. A new method of synthesis
  作者：P.W. Clark、S.F. Dyke

  DOI：10.1016/0022-328x(83)87171-x

  日期：1983.12

  Cyclopalladated complexes of primary, secondary and tertiary bezylamines and of benzalimines have been prepared by the oxidative addition of the corresponding ortho-bromobenzylamine and ortho-halobenzalimine to bid(dibenzylideneacetone)palladium(0). The complexes have been characterised fully as the monomeric triphenylphosphine derivatives.

  通过氧化将相应的邻溴苄胺和邻卤苯甲酰亚胺氧化成二（二苄叉基丙酮）钯（0），可以制备伯，仲和叔苄胺和苯丙胺的环钯配合物。该配合物已被充分表征为单体三苯基膦衍生物。
• Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C−N Bond Formation−Ring-Expansion Process
  作者：Artis Klapars、Sean Parris、Kevin W. Anderson、Stephen L. Buchwald

  DOI：10.1021/ja038565t

  日期：2004.3.1

  A simple method for the preparation of medium ring heterocycles (7-, 8-, 9-, and 10-membered) has been developed. The process employs a Cu-catalyzed coupling of beta-Iactam with an aryl bromide or iodide followed by intramolecular attack of a pendant amino group. In some instances, the intermediate beta-lactam is observable but can be converted to the aza-heterocycle by catalysis. Acetic acid was found to be superior to transition metal complexes as a catalyst for this ring-expansion process.
• Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles
  作者：Sandeep N. Raikar、Helena C. Malinakova

  DOI：10.1021/jo400246d

  日期：2013.4.19

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.