4-[(4-hydroxy-3-methoxybenzylidene)amino]benzoic acid | 63098-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[(4-hydroxy-3-methoxybenzylidene)amino]benzoic acid
• 英文别名: 4-(4-hydroxy-3-methoxybenzylideneamino)benzoic acid；4-vanillylidenamino-benzoic acid；4-Vanillylidenamino-benzoesaeure；4-Vanillalamino-benzoesaeure；N-(3-Methoxy-4-hydroxybenzyliden)-4-aminobenzoesaeure；4-(((4-Hydroxy-3-methoxyphenyl)methylene)amino)benzoic acid；4-[(4-hydroxy-3-methoxyphenyl)methylideneamino]benzoic acid
• CAS: 63098-82-8
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: OGFYWVVHQHRQRU-UHFFFAOYSA-N

物化性质

• 熔点：
  209 °C
• 沸点：
  509.0±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氨基邻苯二甲腈 、 4-[(4-hydroxy-3-methoxybenzylidene)amino]benzoic acid 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.83h， 以53%的产率得到4-[2-hydroxy-3-methoxy-4-(4-carboxybenzylideneamino)phenylazo]phthalonitrile
  参考文献：
  名称：

  Azo-coupled zinc phthalocyanines: Towards broad absorption and application in dye-sensitized solar cells

  摘要：

  The synthesis of symmetrical azo-coupled zinc phthalocyanines (7, 8, 10 and 11) incorporating two spectrally complementary photogenerators (azo dyes and phthalocyanines) by N=N double bonds in a single structure was described. The four sensitizers were fully characterized by Fourier Transform infrared spectroscopy, UV-Vis spectroscopy, proton nuclear magnetic resonance, mass spectrometry, elemental analyses, thermogravimetric analysis and cyclic voltammetry. All the azo-coupled phthalocyanines exhibited broad absorptions covering the range 300-800 nm. The cyclic voltammetry studies indicated that the LUMO and HOMO energy levels of four synthesized azo-coupled phthalocyanines could ensure efficient electron injection and thermodynamically favorable dye regeneration. Thermal stability studies showed that the four sensitizers were stable above 200 degrees C. The new compounds were tested in dye-sensitized solar cells and compound 8 showed the best photovoltaic performance, yielding 2.7% power conversion efficiency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.10.026
• 作为产物：
  描述：

  对氨基苯甲酸 、 香草醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 以60%的产率得到4-[(4-hydroxy-3-methoxybenzylidene)amino]benzoic acid
  参考文献：
  名称：

  肉桂醛和香兰素衍生的甲亚胺的合成：体外对甲酰胆碱酯酶的抑制，抗氧化剂和硅分子对接研究

  摘要：

  在本研究中，我们报告了在三乙胺存在下，使用乙醇作为绿色溶剂，从肉桂醛（C1 - C3）和香兰素（V1 - V3）衍生出甲亚胺的合成方法。对合成的化合物进行了表征，并通过DPPH和乙酰胆碱酯酶（AChE）抑制试验研究了它们的自由基清除活性和抗阿尔茨海默氏性质。通过分子对接和ADME预测确定了化合物的抗阿尔茨海默氏症性质。化合物C1和V1被认为具有IC 50的潜力分别为0.01±0.09 µM和0.31±0.03 µM。以DPPH和ABTS计，C1的抗氧化活性为16.22±0.02 µM和17.2±0.02 µM，而V1的抗氧化活性分别为14.07±0.02 µM和15.06±0.03 µM。在基于分子对接和ADME预测的计算机研究中，偶氮甲碱衍生物作为有效的抗阿尔茨海默病药物的重要性。

  DOI：

  10.1007/s00044-017-2104-6

文献信息

• Synthesis, composition and use of novel therapeutic and cosmetic Schiff base products formed by reaction of a carbonyl containing moeity with a transimination nucleophilic catalyst and the use of transimination nucleophilic catalysts to increase the rate at which carbonyl containing therapeutic and cosmetic actives form Schiff base products with biological amines
  申请人：Isaacman Steven

  公开号：US09365532B1

  公开（公告）日：2016-06-14

  The present invention relates to the synthesis, composition and use of novel moieties formed by reacting a transimination nucleophilic catalyst, molecular or polymeric, with carbonyl-containing therapeutic or cosmetic moieties. The resultant Schiff base product is highly reactive towards transimination with a biological amine. The catalyst and carbonyl-containing moiety can be molecular or polymeric, and the resultant chemical and physical properties of the Schiff base products can be engineered by appropriate selection of said catalyst. The present invention also relates to the synthesis, composition and use of novel moieties that are used as actives in sunless tanning preparations. The present invention also relates to the use of transimination nucleophilic catalysts to increase the rate at which a carbonyl-containing moiety reacts with a biological amine. The present invention also relates to the use of transimination nucleophilic catalysts to increase the rate and efficacy of commercial sunless tanning preparations. Improvements on stability and efficacy of said preparations are disclosed. While the invention has been described in terms of its preferred embodiments, those skilled in the art will recognize that the invention can be practiced with modification within the spirit and scope of the appended claims. Accordingly, the present invention should not be limited to the embodiments as described above, but should further include all modifications and equivalents thereof within the spirit and scope of the description provided herein.

  本发明涉及通过将转移胺亲核催化剂（分子或聚合物）与含羰基的治疗或化妆品基团反应而形成的新颖基团的合成、组成和使用。所得的席夫碱产物对生物胺的转移胺反应具有高度的反应性。催化剂和含羰基基团可以是分子或聚合物，并且通过适当选择所述催化剂可以调控席夫碱产物的化学和物理性质。本发明还涉及合成、组成和使用作为无阳光晒黑制剂中活性成分的新颖基团。本发明还涉及使用转移胺亲核催化剂来增加含羰基基团与生物胺反应的速率。本发明还涉及使用转移胺亲核催化剂来提高商业无阳光晒黑制剂的速率和功效。所述制剂的稳定性和功效的改进被披露。虽然本发明已根据其首选实施方式进行了描述，但技术领域的专业人士将认识到，本发明可以在附图权利要求的精神和范围内进行修改实施。因此，本发明不应仅限于上述描述的实施方式，而应进一步包括本文所提供的描述的精神和范围内的所有修改和等效物。
• 用于识别超氧阴离子的荧光探针及其制备方 法和应用、光纤探头及其制备方法
  申请人：黄淮学院

  公开号：CN107162930B

  公开（公告）日：2019-11-22

  本发明涉及一种用于识别超氧阴离子的荧光探针及其制备方法和应用、光纤探头及其制备方法，属于荧光探针技术领域。用于识别超氧阴离子的荧光探针，具有式Ⅰ所示的结构：式Ⅰ中，Ar和Ar’分别独立地选自苯基、喹啉基、异喹啉基、稠环基、取代基取代的苯基或取代基取代的稠环基，取代基独立地选自羟基或碳原子数为1～4的烷基，R1为碳原子数为1～4的烷基，R2为羟基或氢。本发明中荧光探针具有针对超氧阴离子的荧光敏感性，可与超氧阴离子反应，并导致荧光淬灭，通过探测荧光即可快速识别超氧阴离子，检测灵敏度较高，适用于超氧阴离子的便捷检测。
• Manchot; Furlong, Chemische Berichte, 1909, vol. 42, p. 4389
  作者：Manchot、Furlong

  DOI：——

  日期：——
• Wheeler, Journal of the American Chemical Society, 1913, vol. 35, p. 977
  作者：Wheeler

  DOI：——

  日期：——