4-(naphthalen-1-ylamino)butanoic acid | 16306-59-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(naphthalen-1-ylamino)butanoic acid
• CAS: 16306-59-5
• 化学式: C₁₄H₁₅NO₂
• mdl: MFCD00598967
• 分子量: 229.279
• InChiKey: UCITWWOZBABSKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(naphthalen-1-ylamino)butanoic acid 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids

  摘要：

  A series of monoreactive functional benzo[a]phenoxazinium chlorides with a carboxyl, hydroxyl, amine or chloromethyl group were used as labels in the preparation of long-wavelength fluorescent amino acid bioconjugates. UV-visible and fluorescence studies of all compounds were carried out in ethanol and water at physiological pH. The absorption and emission of all compounds synthesised were in the range 555-640 nm and 632-681 nm, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.005
• 作为产物：
  描述：

  ethyl 4-(naphthalen-1-ylamino)butanoate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到4-(naphthalen-1-ylamino)butanoic acid
  参考文献：
  名称：

  Synthesis of fluorescent water-soluble functionalised benzo[a]phenoxazinium salts

  摘要：

  In order to develop long-wavelength functionalised oxazine dyes with good water solubility and high photostability for biological applications, a series of novel side-chain functionalised benzo[a]phenoxazinium salts were synthesised and characterised. These polycyclic cationic compounds showed strong fluorescence in ethanol and water (pH 7.4), with an emission wavelengths higher than 637 nm, as well as high quantum yields and moderate Stokes' shifts. The photostability of the fluorophores synthesised, under irradiation at 419 nm, was good to excellent in ethanol and moderate in water at physiological pH. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.133

文献信息

• New NIR dyes based on quinolizino[1,9-hi]phenoxazin-6-iminium chlorides: synthesis, photophysics and antifungal activity
  作者：B. Rama Raju、Maria Inês P.S. Leitão、Maria João Sousa、Paulo J.G. Coutinho、M. Sameiro T. Gonçalves

  DOI：10.1016/j.dyepig.2019.107870

  日期：2020.2

  9-hi]phenoxazinium chlorides were evaluated against the yeast Saccharomyces cerevisiae in a broth microdilution assay. It was found that their antifungal activity depended on the substituent at 14-amino position in benzo[a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chlorides, and also on the addition of a fused benzene ring, which occurs in naphtho[2,3-a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chloride. The

  制备了一系列新的基于聚吲哚和萘-1-胺衍生物或蒽-1-胺的喹啉并[1,9- hi ]苯恶嗪鎓染料。这些喹啉并[1，9- hi ]苯恶嗪氯化物的N-末端含有芳族或脂族取代基，以及诸如氯，羟基和羧基的官能团。在酸性和碱性条件下，在无水乙醇和水性介质中研究了这些化合物的光物理行为。这些荧光团分别显示最大675 nm和712 nm的最大吸收和发射，可作为生物学测定中的替代传感工具。 在肉汤微量稀释试验中，针对酵母酿酒酵母评估了所有喹喔啉[1,9- hi ]苯氧嗪鎓氯化物。发现它们的抗真菌活性取决于苯并[ a ]喹啉并[1,9 - hi ]苯恶嗪-14（5 H）-亚胺氯化物中14-氨基位置的取代基，还取决于稠合苯环的添加。发生在萘并[2,3- a ]喹啉并[ 1,9 - hi ]苯恶嗪-14（5 H）-亚氯化亚胺中。苯并[ a ]喹啉并[1,9 - hi ]苯恶嗪-14（5 H）-在杂环核的14-氨基位置具有3-氯丙基取代基的氯化亚胺。
• Ultrasound promoted synthesis of Nile Blue derivatives
  作者：B. Rama Raju、Diogo M.F. Sampaio、M.M. Silva、Paulo J.G. Coutinho、M. Sameiro T. Gonçalves

  DOI：10.1016/j.ultsonch.2013.05.010

  日期：2014.1

  Ultrasound irradiation was used for the first time towards the synthesis of new Nile Blue related benzo[a]phenoxazinium chlorides possessing isopentylamino, (2-cyclohexylethyl)amino and phenethylamino groups at 5-position of the heterocyclic system. The efficacy of sonochemistry was investigated with some of our earlier reported synthesis of benzo[a]phenoxazinium chlorides. This newer protocol proved competent in terms of reaction times and enhanced yields. Photophysical studies carried out in ethanol, water and simulated physiological conditions, revealed that emission maxima occurred in the range 644-656 nm, with high fluorescent quantum yields. Other attractive feature exhibited by these materials includes good thermal stability. These properties might be useful in the development of fluorescent probes for biotechnology. (C) 2013 Elsevier B.V. All rights reserved.
• Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids
  作者：Vânia H.J. Frade、Paulo J.G. Coutinho、João C.V.P. Moura、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tet.2006.12.005

  日期：2007.2

  A series of monoreactive functional benzo[a]phenoxazinium chlorides with a carboxyl, hydroxyl, amine or chloromethyl group were used as labels in the preparation of long-wavelength fluorescent amino acid bioconjugates. UV-visible and fluorescence studies of all compounds were carried out in ethanol and water at physiological pH. The absorption and emission of all compounds synthesised were in the range 555-640 nm and 632-681 nm, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of fluorescent water-soluble functionalised benzo[a]phenoxazinium salts
  作者：Vânia H.J. Frade、M. Sameiro T. Gonçalves、João C.V.P. Moura

  DOI：10.1016/j.tetlet.2006.09.133

  日期：2006.11

  In order to develop long-wavelength functionalised oxazine dyes with good water solubility and high photostability for biological applications, a series of novel side-chain functionalised benzo[a]phenoxazinium salts were synthesised and characterised. These polycyclic cationic compounds showed strong fluorescence in ethanol and water (pH 7.4), with an emission wavelengths higher than 637 nm, as well as high quantum yields and moderate Stokes' shifts. The photostability of the fluorophores synthesised, under irradiation at 419 nm, was good to excellent in ethanol and moderate in water at physiological pH. (c) 2006 Elsevier Ltd. All rights reserved.