1-Naphthyliden-p-bromanilin | 32745-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Naphthyliden-p-bromanilin
• 英文别名: N-(4-bromophenyl)-1-naphthalen-1-ylmethanimine
• CAS: 32745-85-0
• 化学式: C₁₇H₁₂BrN
• 分子量: 310.193
• InChiKey: HSHQJVWYIBCSBM-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C(Solv: ligroine (8032-32-4))
• 沸点：
  452.9±28.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  1-Naphthyliden-p-bromanilin 在 甲基三辛基氯化铵 、 sodium hydroxide 、 锌 作用下， 以 水 为溶剂， 反应 1.5h， 以86%的产率得到4-bromo-N-(naphthalen-1-ylmethyl)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：

  1-萘甲醛 、 4-溴苯胺 以 乙醇 为溶剂， 生成 1-Naphthyliden-p-bromanilin
  参考文献：
  名称：

  供体-受体氮丙啶和亚胺的对映选择性 [3+2] 环加成反应构建 2,5-反式咪唑啉

  摘要：

  报道了与2,2'-二酯氮丙啶和亚胺合成咪唑啉化合物的不对称[3+2]环化。在温和的反应条件下，以高产率和出色的对映选择性获得了一系列手性反式咪唑啉。与之前报道的咪唑啉类化合物的合成方法相比，该方法可以提供具有2,5-反式选择性的咪唑啉类化合物。产物的立体选择性由金属/ N、N'-二氧化物和对照实验表明的底物相互作用决定。

  DOI：

  10.1002/chem.202203757

文献信息

• Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity
  作者：OM Walsh、MJ Meegan、RM Prendergast、T Al Nakib

  DOI：10.1016/s0223-5234(97)86178-8

  日期：1996.1

  The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7 acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.
• Enantioselective Construction of C3-Multifunctionalization α-Hydroxy-β-amino Pyridines via α-Pyridyl Diazoacetate, Water, and Imines for Drug Hunting
  作者：Jian Xue、Zhengli Luo、Jisheng Huang、Yaqi Deng、Suzhen Dong、Shunying Liu

  DOI：10.1021/acs.orglett.2c03987

  日期：2022.12.30

  An asymmetric catalytic approach for the construction of C3-multifunctionalization α-hydroxy-β-amino pyridines has been reported. The products can be accessed by the modulation of two chiral catalysts independently in high yield and with good enantioselectivity. The method features mild reaction conditions and an excellent functional group tolerance. Biological activity analysis shows that the resulting products have a selective antiosteosarcoma activity on 143B cells.
• Economical and efficient aqueous reductions of high melting-point imines and nitroarenes to amines: promotion effects of granular PTFE
  作者：Tao Li、Xiaoxue Cui、Lili Sun、Chunbao Li

  DOI：10.1039/c4ra04528a

  日期：——

  The reductions of high melting-point imines and nitroarenes to amines in aqueous media using Zn powder, granular PTFE (polytetrafluoroethylene), catalytic Aliquat 336 and NH4Cl or 5% NaOH at room temperature have been achieved. A major advantage of this procedure is that the cost of the catalyst is only 1/7200 of that of a previously reported nitroaromatic aqueous reduction catalyst. Altogether 13 imines and 11 nitroarenes were reduced to the corresponding amines with excellent yields. The effects of the amount of granular PTFE, and solubilities and melting points of the substrates, and melting points of the products on the reaction rates are discussed. For the first time, the relationship between the aqueous reaction rates and melting points of the products was investigated, which leads to a conclusion that lower melting-point products form faster than higher melting-point ones in the aqueous reductions. The Aliquat 336, granular PTFE and water are all recyclable.

  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。
• Enantioselective [3+2] Cycloaddition of Donor‐Acceptor Aziridines and Imines to Construct 2,5‐ <i>trans</i> ‐Imidazolidines
  作者：Jianglin Qiao、Shiyu Wang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.202203757

  日期：2023.3.28

  An asymmetric [3+2] annulation to synthesize imidazolidine compounds with 2,2’-diester aziridines and imines was reported. A series of chiral trans-imidazolidines were obtained in high yields with outstanding enantioselectivities under mild reaction conditions. Compared to the previously reported method of synthesizing imidazolines, this method could offer the imidazoline compounds with 2,5-trans-selectivity

  报道了与2,2'-二酯氮丙啶和亚胺合成咪唑啉化合物的不对称[3+2]环化。在温和的反应条件下，以高产率和出色的对映选择性获得了一系列手性反式咪唑啉。与之前报道的咪唑啉类化合物的合成方法相比，该方法可以提供具有2,5-反式选择性的咪唑啉类化合物。产物的立体选择性由金属/ N、N'-二氧化物和对照实验表明的底物相互作用决定。