1-(2,4-dimethoxyphenyl)-N-phenylmethanimine | 121133-23-1

• 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: 1-(2,4-dimethoxyphenyl)-N-phenylmethanimine
• 英文别名: (E)-1-(2,4-dimethoxyphenyl)-N-phenylmethanimine；(E)-N-[(2,4-dimethoxyphenyl)methylidene]aniline；(E)-N-(2,4-dimethoxybenzylidene)aniline；N-phenyl-2,4-dimethoxybenzylidenimine
• CAS: 121133-23-1
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: DUGFMSCFQCJGBY-LFIBNONCSA-N

物化性质

• 沸点：
  387.2±32.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethoxyphenyl)-N-phenylmethanimine 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以38%的产率得到7,9-dimethoxyphenanthridine
  参考文献：
  名称：

  Lewis acid promoted photocyclization of arylimines. Studies directed towards the synthesis of pentacyclic natural products.

  摘要：

  DOI：

  10.1016/s0040-4039(00)80719-4
• 作为产物：
  描述：

  苯胺 、 2,4-二甲氧基苯甲醛 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到1-(2,4-dimethoxyphenyl)-N-phenylmethanimine
  参考文献：
  名称：

  Pi-pi堆积与立体选择性控制中的空间效应：合成高syn-1,2-二芳基丙胺的非对映选择性。

  摘要：

  N-芳基亚烷基胺与衍生自2-（对甲苯基亚磺酰基）甲苯（S）-1和（S）-2的亚磺酰基苄基碳负离子反应，在C1处提供1,2-二芳基乙基-和1,2-二芳基丙胺衍生物的差向异构混合物。亚磺酰基完全控制（S）-2反应中C2处的构型。C1处的构型取决于与亚氨基碳原子相邻的环的电子密度，该电子密度通过与环连接至碳负离子中心的pi-pi堆积相互作用进行调节。通过用适当的取代基修饰亚芳基胺环的受体特性来控制立体选择性，通过给电子基团可以在C1上形成高选择性（R）构型。N-（2,4，

  DOI：

  10.1002/chem.200601893

文献信息

• Highly Stereoselective Reactions of <i>γ</i>-Sulfinyl Carbanions with Achiral Imines
  作者：José Luis García Ruano、José Alemán、Alejandro Parra

  DOI：10.1080/10426500590910800

  日期：2005.3.2

  Abstract Lithium 2-p-tolylsulfinylbenzyl carbanions react with different N-substituted imines affording 1,2-diaryl ethyl (and propyl) amines with a high stereoselectivity control at both benzyllic (only dependent of the sulfur configuration) and iminic carbons. The anti:syn ratio, ranging between > 96: < 4 and < 2: > 98, dependent on the electronic density at nitrogen.

  摘要 锂 2-对甲苯基亚磺酰基苄基碳负离子与不同的 N-取代亚胺反应，得到 1,2-二芳基乙基（和丙基）胺，在苄基（仅取决于硫构型）和亚胺碳上均具有高立体选择性控制。anti:syn 比值介于 > 96: < 4 和 < 2: > 98 之间，取决于氮处的电子密度。
• A Highly Selective Manganese-Catalyzed Synthesis of Imines under Phosphine-Free Conditions
  作者：Huining Chai、Kun Yu、Bo Liu、Weiqiang Tan、Guangyao Zhang

  DOI：10.1021/acs.organomet.9b00769

  日期：2020.1.13

  An efficient and highly selective phosphine-free NN-manganese(I) complex catalyst system was developed for the acceptorless dehydrogenative coupling of alcohols with amines to form imines. The coupling reactions underwent at 3 mol % catalyst loading, and a large range of alcohols and amines with diverse functional groups was applied, including challenging diol and diamine. The target imine products were obtained in good to excellent yields. The present work provides an alternative method to construct highly active nonprecious metal complex catalysts based on phosphine-free ligands.
• Supramolecular Catalysis of Strecker Reaction in Water under Neutral Conditions in the Presence of β-Cyclodextrin
  作者：K. Surendra、N. Srilakshmi Krishnaveni、A. Mahesh、K. Rama Rao

  DOI：10.1021/jo052510n

  日期：2006.3.1

  [GRAPHICS]An environmentally benign and highly efficient procedure for the nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction) has been developed under biomimetic conditions in water in the presence of beta-cyclodextrin to afford alpha-aminonitriles in quantitative yields. The use of cyclodextrin precludes the use of either acid or base, and the catalyst can be recycled a number of times without loss in activity.
• Selective Synthesis of β-Amino Esters and β-Lactams by Rhodium-catalyzed Reformatsky-Type Reaction
  作者：Toshio Honda、Kazuo Kanai、Hitoshi Wakabayashi

  DOI：10.3987/com-02-s(m)10

  日期：——
• Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
  作者：Dominik Hager、David W. C. MacMillan

  DOI：10.1021/ja5102695

  日期：2014.12.10

  The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C-H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical-radical coupling with secondary aldimines affords a variety of β-amino ether products in good to excellent yields. Mechanistic studies suggest that a reductive quenching pathway of the photocatalyst is operable.