N-(4-bromophenyl)-1-(2,4-dichlorophenyl)methanimine | 14632-35-0

• 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-(4-bromophenyl)-1-(2,4-dichlorophenyl)methanimine
• 英文别名: N-(2.4-Dichlor-benzyliden)-4-brom-anilin；4-Bromo-N-(2,4-dichlorobenzylidene)aniline
• CAS: 14632-35-0
• 化学式: C₁₃H₈BrCl₂N
• 分子量: 329.023
• InChiKey: VMLIQUBRQZTNBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-1-(2,4-dichlorophenyl)methanimine 在 甲基三辛基氯化铵 、 sodium hydroxide 、 锌 作用下， 以 水 为溶剂， 反应 0.75h， 以92%的产率得到4-bromo-N-[(2,4-dichlorophenyl)methyl]aniline
  参考文献：
  名称：

  Economical and efficient aqueous reductions of high melting-point imines and nitroarenes to amines: promotion effects of granular PTFE

  摘要：

  使用 Zn 粉末、颗粒状 PTFE（聚四氟乙烯）、催化剂 Aliquat 336 和 NH4Cl 或 5%NaOH，在室温下实现了高熔点亚胺和硝基烯烃在水介质中还原成胺的过程。这种方法的一个主要优点是催化剂的成本仅为之前报道的硝基芳烃水还原催化剂的 1/7200。总共有 13 个亚胺和 11 个硝基烯烃被还原成相应的胺，而且收率极高。讨论了颗粒状聚四氟乙烯的用量、底物的溶解度和熔点以及产物的熔点对反应速率的影响。首次研究了水反应速率与产物熔点之间的关系，从而得出结论：在水还原反应中，低熔点产物的形成速度快于高熔点产物。Aliquat 336、粒状聚四氟乙烯和水均可回收利用。

  DOI：

  10.1039/c4ra04528a
• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 4-溴苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到N-(4-bromophenyl)-1-(2,4-dichlorophenyl)methanimine
  参考文献：
  名称：

  四氯-1,3-奥氮平衍生物的合成，表征及生物活性评价

  摘要：

  在（2 + 5→7）环加成条件下，通过使席夫碱1a-10a与四氯邻苯二甲酸酐（TCPA）反应，合成了6,7,8,9-四氯[1,3]氮杂ze庚因-1,5-二酮衍生物1b-10b反应条件。使用TLC监测所有反应。傅立叶变换红外光谱和熔点已用于表征席夫碱。使用FT IR，1 H NMR及其熔点对奥氮平化合物1b – 10b进行了表征。评估了奥氮平化合物对细菌类型（金黄色葡萄球菌，大肠杆菌，克雷伯菌属）和真菌（土pp属）的生物活性。已经观察到针对使用过的细菌和真菌菌株具有可变的活性。

  DOI：

  10.17344/acsi.2019.5264

文献信息

• Ir-Catalyzed C−H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group
  作者：Yun-Fei Zhang、Bin Wu、Zhang-Jie Shi

  DOI：10.1002/chem.201603805

  日期：2016.12.5

  Ir‐catalyzed sp2 C−H amidation of aldehydes with various anilines as stoichiometric or catalytic directing groups was accomplished. A wide range of substrates were selectively amidated in good to excellent yields with broad functional group tolerance. The iridacycle complexes were isolated, characterized, and proved as key intermediates. Kinetic studies and Hammett plots provided detailed understandings

  用各种苯胺作为化学计量或催化方向的基团，对醛进行了Ir催化的sp 2 CH酰胺化反应。以良好的产率和优异的产率选择性选择性地酰胺化各种底物，并具有宽泛的官能团耐受性。分离，表征并证明了iridacycle复合物是关键中间体。动力学研究和Hammett图提供了对这种酰胺化反应的详细了解。根据机理，证明了富电子的ArSO 2 N 3对于分子间sp 3 CH酰胺化有效。
• Direct Metal-Free C-H Functionalization of Cyclic Ethers with Schiff Bases Through an Azobisisobutyronitrile-Initiated Radical Chain Process
  作者：Haipeng Zeng、Dengfu Lu、Yuefa Gong

  DOI：10.1002/ejoc.201701288

  日期：2017.12.29

  represents an efficient way to form C–C bonds and construct 1,2-amino ethers. Despite being a net redox-neutral process, most examples require excess amounts of radical reagents or oxidants to continuously generate the radical species. Herein, we report an atom-economic protocol for the radical addition of cyclic ethers to imines without the need for any oxidant, metal salt, delicate catalyst, or UV irradiation

  环醚与亚胺的自由基引发的 C-H 键官能化代表了形成 C-C 键和构建 1,2-氨基醚的有效方法。尽管是一个净氧化还原中性过程，但大多数例子需要过量的自由基试剂或氧化剂来连续产生自由基物种。在此，我们报告了一种无需任何氧化剂、金属盐、精细催化剂或紫外线照射即可将环醚自由基加成到亚胺的原子经济协议。在少量 AIBN (2 mol-%) 的存在下，四氢呋喃与各种亚胺顺利进行反应，以中等至良好的产率得到 1,2-氨基醚。初步的机理研究表明，这种转变可能通过一个自由基链过程进行，以氢原子提取作为速率决定步骤。
• Triazolines. XXIX. 1,5-diaryl-Δ²-1,2,3-triazolines as aphicides: Mechanism of action via aziridine formation
  作者：Pankaja K. Kadaba

  DOI：10.1002/ps.2780420407

  日期：1994.12

  AbstractThe aphicidal activity of 21 different 1,5‐diphenyl‐Δ2‐1,2,3‐triazolines, conveniently prepared utilizing the catalytic effect of water on the 1,3‐cyclo‐addition of diazomethane to Schiff bases in aqueous dioxane, was evaluated. Triazolines bearing an o‐Cl substituent on the C‐phenyl, either alone (4) or in combination with a m‐ and/or a p‐substituent on the N‐phenyl (14, 15, 17 and 18), showed significant activity, with a combined m‐, p‐ substitution on the N‐phenyl the most effective (17 and 18). While an o‐Cl substituent led to greater activity than an o‐NO2 group, the introduction of an additional p‐Cl substituent on the C‐phenyl eliminated activity (21).The aphicidal activity of triazoline 18 was found to be dependent on the presence of UV light. Since fluorescent lighting used in the testing procedure contains UV light and since triazolines undergo photolysis when exposed to UV light to yield aziridines, it was logical to conclude that the aphicidal activity of the triazolines was, in fact, derived from the aziridines formed during the testing procedure. This mechanism of action was confirmed by preparing the aziridines 22, 23 and 24 corresponding to the active triazolines 14, 15 and 18, and showing that they possessed aphicidal activity equal to or better than that of the triazolines, and by the activity observed in several other structurally related aziridine analogues (25–28). Unlike aziridinyl phosphorous compounds, the aziridines described here are not mutagenic in the Ames assay and thus afford a safer class of pesticides.
• Aza-Diels–Alder Reactions with Lanthanide Triflates: Syntheses of Quinoline and Phenanthridine Derivatives
  作者：Kadir Turhan、Emel Pelit、Zuhal Turgut

  DOI：10.1080/00397910802585902

  日期：2009.4.22

  The aza-Diels-Alder reactions of cyclopentadiene and cyclo-1,3-hexadiene with various substituted N-arylimines in the presence of Yb/Sc triflates as catalyst in MeCN at room temperature gave quinoline and phenanthridine derivatives in moderate to high yields. Some of the cycloaddition reactions were carried out in ionic liquid.
• Synthesis and Characterization of Tetrachloro-1,3-Oxazepine Derivatives and Evaluation of their Biological Activities
  作者：Abdullah Hussein Kshash

  DOI：10.17344/acsi.2019.5264

  日期：——

  6,7,8,9-Tetrachloro[1,3]oxazepine-1,5-dione derivatives 1b – 10b have been synthesized by reacting Schiff bases 1a – 10a with tetrachlorophthalic anhydride (TCPA) under (2 + 5 → 7) cycloaddition reaction conditons. All reactions had been monitored using TLC. FT IR and melting points have been used to characterize the Schiff bases; oxazepine compounds 1b – 10b were characterized using FT IR, 1 H NMR

  在（2 + 5→7）环加成条件下，通过使席夫碱1a-10a与四氯邻苯二甲酸酐（TCPA）反应，合成了6,7,8,9-四氯[1,3]氮杂ze庚因-1,5-二酮衍生物1b-10b反应条件。使用TLC监测所有反应。傅立叶变换红外光谱和熔点已用于表征席夫碱。使用FT IR，1 H NMR及其熔点对奥氮平化合物1b – 10b进行了表征。评估了奥氮平化合物对细菌类型（金黄色葡萄球菌，大肠杆菌，克雷伯菌属）和真菌（土pp属）的生物活性。已经观察到针对使用过的细菌和真菌菌株具有可变的活性。