4-methylbenzylidene-4-carboxyaniline | 3939-40-0

• 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: 4-methylbenzylidene-4-carboxyaniline
• 英文别名: 4-(4-methyl-benzylidenamino)-benzoic acid；4-(4-Methyl-benzylidenamino)-benzoesaeure；4-(4-Methyl-benzalamino)-benzoesaeure；4-[(4-Methylphenyl)methylideneamino]benzoic acid
• CAS: 3939-40-0
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: HJGVCPYOCTVHBH-UHFFFAOYSA-N

物化性质

• 熔点：
  241 °C
• 沸点：
  431.4±38.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methylbenzylidene-4-carboxyaniline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-((3R,4R)-3-Acetoxy-2-oxo-4-p-tolyl-azetidin-1-yl)-benzoic acid
  参考文献：
  名称：

  Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(97)86178-8
• 作为产物：
  描述：

  对甲基苯甲醛 、 对氨基苯甲酸 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以74%的产率得到4-methylbenzylidene-4-carboxyaniline
  参考文献：
  名称：

  氢键和甲亚胺基团取向对苄叉苯胺化合物液晶性能的影响

  摘要：

  这项研究研究了取代基和氢键，亚胺键的取向对亚苄基苯胺化合物作为液晶的行为的影响。通过苯胺及其取代的衍生物与4-甲酰基苯甲酸反应，合成了化合物4-羧基亚苄基-4-X-苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1a-6a。苯甲醛及其取代的衍生物与4-氨基苯甲酸的无水乙醇反应，合成了化合物4-X-亚苄基-4-羧基苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1b-6b作为溶剂。通过FT IR和1 H NMR光谱对合成的化合物进行表征，使用差示扫描量热法（DSC）和偏振光学显微镜（POM）技术研究液晶性能。根据介晶性质，已证明化合物2b-4b是双晶的，具有近晶相和向列相，化合物5b，6b是单晶的，具有向列相，而化合物1a-6a和1b没有显示出中间相。对于化合物1a – 6a的氢键结合和亚胺键的反转（与化合物1b – 6b相比）导致其介晶特性不存在。

  DOI：

  10.17344/acsi.2019.5648

文献信息

• Synthesis of novel β-amino ketones containing a p-aminobenzoic acid moiety and evaluation of their antidiabetic activities
  作者：GuangXia Tang、JuFang Yan、Li Fan、Jin Xu、XiaoLi Song、Li Jiang、LingFei Luo、DaCheng Yang

  DOI：10.1007/s11426-012-4816-2

  日期：2013.4

  The synthesis of two series of β-amino ketones containing a p-aminobenzoic acid moiety (TM-1 and TM-2) using a modified protocol of the Mannich reaction is reported. The molecular structures of a total of tweenty three new target compounds were characterized by 1H NMR, 13C NMR, ESI-MS and HR-MS. Subsequently, their antidiabetic activities were screened in vitro. The α-glucodase inhibition (α-GI) activity of compound 1e reached a remarkable level of 66.50%. The peroxisome proliferator-activated receptor (PPAR) relative activation activities of six compounds are above 80%, and in particular 2i displays an unprecedentedly high PPAR of 130.91%. The structure-activity relationships of the compounds were established. 2i is also subject to further in-depth investigation.

  报道了使用改进的Mannich反应方案合成了包含对氨基苯甲酸部分的两种系列的β-氨基酮（TM-1和TM-2）。总共23个新目标化合物的分子结构通过1H NMR、13C NMR、ESI-MS和HR-MS进行了表征。随后，它们在体外进行了抗糖尿病活性筛选。化合物1e的α-葡萄糖苷酶抑制（α-GI）活性达到了显著的66.50%水平。六个化合物的过氧化物酶体增殖物激活受体（PPAR）相对激活活性均超过80%，其中特别是2i显示了前所未有的高PPAR值130.91%。建立了这些化合物的结构-活性关系。2i也正在进行更深入的研究。
• Manchot; Furlong, Chemische Berichte, 1909, vol. 42, p. 4389
  作者：Manchot、Furlong

  DOI：——

  日期：——
• 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.
• The Effect of Hydrogen Bonding and Azomethine Group Orientation on Liquid Crystal Properties in Benzylidene Aniline Compounds
  作者：Abdullah Hussein Kshash

  DOI：10.17344/acsi.2019.5648

  日期：——

  behavior of benzylidene aniline compounds as liquid crystals (LC). Compounds 4-carboxy benzylidene-4-X-aniline (X = H, F, Cl, Br, CH 3 , OCH 3 ) 1a – 6a were synthesized by the reaction of aniline and its substituted derivatives with 4-formylbenzoic acid. Compounds 4-X-benzylidene-4-carboxy aniline (X = H, F, Cl, Br, CH 3 , OCH 3 ) 1b – 6b were synthesized by the reaction of benzaldehyde and its substituted

  这项研究研究了取代基和氢键，亚胺键的取向对亚苄基苯胺化合物作为液晶的行为的影响。通过苯胺及其取代的衍生物与4-甲酰基苯甲酸反应，合成了化合物4-羧基亚苄基-4-X-苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1a-6a。苯甲醛及其取代的衍生物与4-氨基苯甲酸的无水乙醇反应，合成了化合物4-X-亚苄基-4-羧基苯胺（X = H，F，Cl，Br，CH 3，OCH 3）1b-6b作为溶剂。通过FT IR和1 H NMR光谱对合成的化合物进行表征，使用差示扫描量热法（DSC）和偏振光学显微镜（POM）技术研究液晶性能。根据介晶性质，已证明化合物2b-4b是双晶的，具有近晶相和向列相，化合物5b，6b是单晶的，具有向列相，而化合物1a-6a和1b没有显示出中间相。对于化合物1a – 6a的氢键结合和亚胺键的反转（与化合物1b – 6b相比）导致其介晶特性不存在。