6-(3-chloropropoxy)-N-propylnaphthalen-1-amine | 1392209-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(3-chloropropoxy)-N-propylnaphthalen-1-amine
• CAS: 1392209-35-6
• 化学式: C₁₆H₂₀ClNO
• 分子量: 277.794
• InChiKey: YLPQTWBIFUMRKA-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±25.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(3-chloropropoxy)-N-propylnaphthalen-1-amine 、 5-((3-chloropropyl)amino)-2-nitrosophenol hydrochloride 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以37%的产率得到3-chloro-N-(2-(3-chloropropoxy)-5-(propylamino)-9H-benzo[a]phenoxazin-9-ylidene)propan-1-aminium chloride
  参考文献：
  名称：

  Synthesis and photophysical properties of side-chain chlorinated benzo[a]phenoxazinium chlorides

  摘要：

  Novel water-soluble benzo[a]phenoxazinium chlorides mono- or disubstituted with 3-chloropropyl groups at the amine of position 9, and also at the hydroxyl function at position 2, were synthesized. These compounds possessing one, two or three chlorinated terminals displayed fluorescence emission in ethanol and water in the range 644-666 nm and 649-676 nm, respectively, with fluorescence quantum yields from 0.26 to 0.38.It was found that this type of molecules is involved in acid-base equilibrium and tautomerization with localized positive charge. Ab-initio ground and excited state DFT calculations were made for the various possible tautomers of a model compound. Preliminary studies of the photophysical behaviour of these compounds in AOT/cyclohexane reverse micelles with low water content (omega(o)=[Water]/[AOT]<= 5) showed that they interact strongly with the head groups in the interface feeling the presence of an increased amount of water. At very low omega(o) values, AOT molecules promote the tautomerization process allowing it to follow both in absorption and emission spectra. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.035
• 作为产物：
  描述：

  5-氨基-2-萘酚 在 caesium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.5h， 生成 6-(3-chloropropoxy)-N-propylnaphthalen-1-amine
  参考文献：
  名称：

  Synthesis and photophysical properties of side-chain chlorinated benzo[a]phenoxazinium chlorides

  摘要：

  Novel water-soluble benzo[a]phenoxazinium chlorides mono- or disubstituted with 3-chloropropyl groups at the amine of position 9, and also at the hydroxyl function at position 2, were synthesized. These compounds possessing one, two or three chlorinated terminals displayed fluorescence emission in ethanol and water in the range 644-666 nm and 649-676 nm, respectively, with fluorescence quantum yields from 0.26 to 0.38.It was found that this type of molecules is involved in acid-base equilibrium and tautomerization with localized positive charge. Ab-initio ground and excited state DFT calculations were made for the various possible tautomers of a model compound. Preliminary studies of the photophysical behaviour of these compounds in AOT/cyclohexane reverse micelles with low water content (omega(o)=[Water]/[AOT]<= 5) showed that they interact strongly with the head groups in the interface feeling the presence of an increased amount of water. At very low omega(o) values, AOT molecules promote the tautomerization process allowing it to follow both in absorption and emission spectra. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.035

文献信息

• Bifunctionalised long-wavelength fluorescent probes for biological applications
  作者：A. Daniela G. Firmino、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tetlet.2012.07.004

  日期：2012.9

  The synthesis of benzo[a]phenoxazinium chlorides which are bifunctionalised in position 2 with 4-ethoxy-4-oxobutoxyl, 3-hydroxypropoxyl or 3-chloropropoxyl groups, and in position 9 with the (aminopropyl)amino group, was efficiently performed. The covalent labelling of valine was carried out by using one of the new fluorophores obtained. Photophysical studies in the homogeneous media of ethanol, distilled

  有效地合成了在2-位带有4-乙氧基-4-氧代丁氧基，3-羟基丙氧基或3-氯丙氧基的双官能化苯并[ 9]在（氨基丙基）氨基的双官能化的苯并[ a ]苯恶嗪氯化物。通过使用获得的新的荧光团之一进行缬氨酸的共价标记。在乙醇，蒸馏水和模拟生理条件的均质介质中进行的光物理研究表明，所有化合物均在610至651 nm范围内吸收和发射。
• Synthesis and photophysical properties of side-chain chlorinated benzo[a]phenoxazinium chlorides
  作者：B. Rama Raju、A. Daniela G. Firmino、A. Luísa S. Costa、Paulo J.G. Coutinho、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tet.2013.01.035

  日期：2013.3

  Novel water-soluble benzo[a]phenoxazinium chlorides mono- or disubstituted with 3-chloropropyl groups at the amine of position 9, and also at the hydroxyl function at position 2, were synthesized. These compounds possessing one, two or three chlorinated terminals displayed fluorescence emission in ethanol and water in the range 644-666 nm and 649-676 nm, respectively, with fluorescence quantum yields from 0.26 to 0.38.It was found that this type of molecules is involved in acid-base equilibrium and tautomerization with localized positive charge. Ab-initio ground and excited state DFT calculations were made for the various possible tautomers of a model compound. Preliminary studies of the photophysical behaviour of these compounds in AOT/cyclohexane reverse micelles with low water content (omega(o)=[Water]/[AOT]<= 5) showed that they interact strongly with the head groups in the interface feeling the presence of an increased amount of water. At very low omega(o) values, AOT molecules promote the tautomerization process allowing it to follow both in absorption and emission spectra. (c) 2013 Elsevier Ltd. All rights reserved.