N-propyl-4-hydroxybenzylideneamine | 106493-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-propyl-4-hydroxybenzylideneamine
• 英文别名: 4-[(Propylimino)methyl]benzenol；4-(propyliminomethyl)phenol
• CAS: 106493-25-8
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: ZGWLQZGCQPBEIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  284.8±23.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-propyl-4-hydroxybenzylideneamine 在 甲醇 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-(4-hydroxybenzyl)-N-propylbenzamide
  参考文献：
  名称：

  Methyl-triflate-mediated dearylmethylation of N-(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

  摘要：

  在无金属条件下，在水介质中通过亲电脱芳香化/重芳香化实现了N-(芳甲基)羧酰胺的去芳甲基化。

  DOI：

  10.1039/c9gc00176j
• 作为产物：
  描述：

  正丙胺 、 对羟基苯甲醛 以 甲醇 为溶剂， 反应 12.0h， 生成 N-propyl-4-hydroxybenzylideneamine
  参考文献：
  名称：

  Methyl-triflate-mediated dearylmethylation of N-(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

  摘要：

  在无金属条件下，在水介质中通过亲电脱芳香化/重芳香化实现了N-(芳甲基)羧酰胺的去芳甲基化。

  DOI：

  10.1039/c9gc00176j

文献信息

• Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides
  作者：Janusz Kowalik、Anthony Baldridge、Laren Tolbert

  DOI：10.1055/s-0029-1218796

  日期：2010.7

  A 2+3 condensation of a wide assortment of Schiff bases, prepared from aromatic aldehydes and primary amines, with methyl 2-(1-ethoxyethylideneamino)acetate allows convenient access to an extensive family of substituted 4-arylideneimidazolin-5-one analogues of the green fluorescent protein (GFP) chromophore. 4-arylideneimidazolin-5-one - azomethine ylide - Schiff bases - heterocycle - 2+3 cycloaddition

  由芳族醛和伯胺制得的各种席夫碱与2-（1-乙氧基乙叉基氨基）乙酸甲酯的2 + 3缩合反应可方便地获得广泛的取代的4-芳基亚氨基咪唑啉-5-酮类似物家族绿色荧光蛋白（GFP）生色团。 4-芳基亚胺达唑啉-5-酮-甲亚胺叶立德-席夫碱-杂环-2 + 3环加成
• Efficient Microwave-Assisted Solvent-Free Synthesis of N-Substituted Aldimines
  作者：Françoise Texier-Boullet、Ludovic Paquin、Jack Hamelin

  DOI：10.1055/s-2006-926429

  日期：2006.5

  react with various aromatic aldehydes in the absence of any catalyst, solid support, or solvent, to give imines after a reaction time of eight minutes under microwave irradiation by a clean and very efficient process (yields: 75-100%). In the case of volatile amine, methylamine, 1,3-dimethylurea dispersed on montmorillonite Kl 0 is used as an amine precursor to prepare the corresponding imines.

  在没有任何催化剂、固体载体或溶剂的情况下，纯净的非挥发性胺与各种芳香醛反应，在微波照射下通过清洁且非常有效的工艺反应 8 分钟后得到亚胺（产率：75-100% ）。在挥发性胺的情况下，分散在蒙脱石Kl 0 上的甲胺、1,3-二甲基脲用作胺前体以制备相应的亚胺。
• Fluorometric sensing of Hg2+ ions in aqueous medium by nano-aggregates of a tripodal receptor
  作者：Ajnesh Singh、Simanpreet Kaur、Narinder Singh、Navneet Kaur

  DOI：10.1039/c3ob42200c

  日期：——

  Two new tripodal receptors (1–2) have been synthesized and characterized by various spectroscopic techniques. The nano-aggregates of 1 and 2 (N1 and N2) have been prepared by a re-precipitation method in aqueous medium and have shown different photo-physical properties. Nano-aggregates of 1 (N1) can selectively recognize Hg2+ in aqueous medium in the presence of other metal ions with enhancement in fluorescent intensity. The response was linearly proportional to the concentration of Hg2+ in the range 0–10 μM with a detection limit of 2.4 nM. The mechanism of selective binding of Hg2+ by N1 has also been supported by theoretical studies. To the best of our knowledge, this work represents the first report on substituted thiourea based nano-aggregates for nano-molar detection of mercury in aqueous medium.

  合成并表征了两种新的三足受体（1-2），采用了多种光谱技术。通过在水相中重沉淀法制备了1和2的纳米聚集体（N1和N2），并显示出不同的光物理特性。1的纳米聚集体（N1）能够在存在其他金属离子的情况下选择性识别水相中的Hg2+，并增强荧光强度。该响应与0-10 μM范围内Hg2+的浓度成线性比例关系，检测限为2.4 nM。理论研究也支持了N1对Hg2+选择性结合的机制。根据我们所知，这项工作是基于取代硫脲的纳米聚集体在水相中进行纳摩尔级汞检测的首次报道。
• Novel caffeic acid amide antioxidants: Synthesis, radical scavenging activity and performance under storage and frying conditions
  作者：Felix Aladedunye、Yohann Catel、Roman Przybylski

  DOI：10.1016/j.foodchem.2011.08.021

  日期：2012.2

  Twelve novel dihydro-caffeic acid amides were synthesised in good yields and fully characterised by 1H NMR, 13C NMR, and MS. Their radical scavenging activities were assessed by DPPH assay. Additionally, their abilities to protect polyunsaturated oils under accelerated storage and frying conditions were evaluated. All the new compounds possessed significantly higher radical scavenging activities than

  以高收率合成了十二种新颖的二氢咖啡酸酰胺，并通过1 H NMR进行了全面表征，131 H NMR和MS。通过DPPH分析评估了它们的自由基清除活性。此外，评估了它们在加速储存和油炸条件下保护多不饱和油的能力。所有这些新化合物都具有比α-生育酚和丁基化羟基甲苯（BHT）更高的自由基清除活性。N-癸基-N-（3,5-二甲氧基-4-羟基苄基）-3-（3,4-二羟基苯基）丙酰胺的自由基清除活性分别比α-生育酚和BHT高1.7和4倍。在储存期结束时，用α-生育酚和BHT强化的菜籽油三酰甘油（CTAG）中氢过氧化物的各自含量分别比含酰胺的CTAG高6.1和1.4倍。油炸试验表明，含有N-癸基-N-苄基-3-（3,4-二羟基苄基）丙酰胺的CTAG为1.3、1.4，通过总极性化合物的量评估，其稳定性分别比用二氢咖啡酸，α-生育酚和BHT强化的油高1.6倍。而且，这些化合物具有显着的热稳定性，使其适合油炸应用。
• Development of chemosensor for Sr²⁺using organic nanoparticles: application of sensor in product analysis for oral care
  作者：Simanpreet Kaur、Amanpreet Kaur、Navneet Kaur、Narinder Singh

  DOI：10.1039/c4ob01234h

  日期：——

  A new series of compounds has been developed for the recognition of metal ions and it was found that the position of substituent in the organic compound proved to be the deciding factor for the development of a chemosensor. Reprecipitation method was used to develop organic nanoparticles (ONPs) in aqueous medium and the suspension of ONP in aqueous medium remained stable for one month. These ONPs were studied for their recognition abilities using fluorescence spectroscopy and only ONPs of compound 1 resulted in a sensor for Sr2+ and the sensor activities were found to be unaffected by the presence of any other cation. The sensor was successfully used to investigate the level of Sr2+ in an oral gel, as well as toothpastes used to cure sensitive teeth.

  开发了一系列新的化合物来识别金属离子，并且发现有机化合物中取代基的位置被证明是化学传感器开发的决定因素。采用再沉淀法在水介质中制备有机纳米粒子（ONP），ONP在水介质中的悬浮液可保持稳定1个月。使用荧光光谱研究了这些 ONP 的识别能力，只有化合物 1 的 ONP 产生了 Sr2+ 传感器，并且发现传感器活性不受任何其他阳离子存在的影响。该传感器已成功用于研究口腔凝胶以及用于治疗敏感牙齿的牙膏中的 Sr2+ 水平。