methyl 3-(naphthalen-1-ylamino)propanoate | 6580-20-7

• 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: methyl 3-(naphthalen-1-ylamino)propanoate
• 英文别名: methyl N-naphthalen-1-yl-beta-alaninate
• CAS: 6580-20-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: CXNYTJOBIQYVJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(naphthalen-1-ylamino)propanoate 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[3-(naphthalen-1-ylamino)propanoyl] alanine methyl ester
  参考文献：
  名称：

  Fluorescence derivatisation of amino acids in short and long-wavelengths

  摘要：

  3-(Naphthalen-1-ylamino)propanoic acid was coupled to the amino group of the main and lateral chains of various amino acids in order to evaluate its applicability as a fluorescent derivatising reagent. The resulting amino acid derivatives are strongly fluorescent with a maximum emission of about 415 run. Condensation of these derivatives with 5-ethylamino-4-methyl-2-nitrosophenol hydrochloride resulted in the corresponding blue benzo[a]phenoxazinium conjugates, also revealing strong fluorescence in ethanol and water at physiological pH and good quantum yields, but with emission wavelengths between 644 and 657 nm, which was preferable in biological assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.070
• 作为产物：
  描述：

  3-溴丙酸甲酯 、 1-萘胺 生成 methyl 3-(naphthalen-1-ylamino)propanoate
  参考文献：
  名称：

  短波长和长波长功能化探针的合成：氨基酸标记和光物理研究

  摘要：

  以不同的方式对短和长波长在主链和侧链的N或C末端的α-氨基酸进行荧光标记。合成的N- [3-（萘-1-基氨基）丙酰基]氨基酸甲酯在电磁波谱的可见光区域（〜415 nm）表现出强荧光。这些化合物与5-二乙基氨基-2-亚硝基苯酚或5-乙基氨基-4-甲基-2-亚硝基苯酚缩合产生苯并[ a ]吩恶嗪衍生物，最大发射波长移至高于644 nm的值。通过5-乙基氨基-4-甲基-2-亚硝基苯酚与N的反应合成新型功能化的5,9-二氨基苯并[ a ]苯恶嗪鎓盐取代的1-萘胺及其在缬氨酸N或C末端的共价标记中的使用，产生了具有长波长发射（644–653 nm）的衍生物。使用合成的化合物在不同溶剂和受控pH中进行了光物理研究。还初步评估了阳离子多环杂环化合物在乙醇和水中在生理pH值下的光稳定性。

  DOI：

  10.1016/j.tet.2007.09.042

文献信息

• Functionalized Ionic Liquid Promoted Aza-Michael Addition of Aromatic Amines
  作者：Xiao-Bing Liu、Ming Lu、Ting-Ting Lu、Guo-Liang Gu

  DOI：10.1002/jccs.201000180

  日期：2010.12

  A functionalized ionic liquid, 3‐(N,N‐dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]) has been used as catalyst for the aza‐Michael reactions of aromatic amines with α,β‐unsaturated compounds at room temperature to produce β‐amino compounds in good yields. The catalyst can be reused for several times without obvious loss of the catalytic activity.

  一种功能化的离子液体3-（N，N-二甲基十二烷基铵）丙烷磺酸硫酸氢盐（[DDPA] [HSO 4 ]）已用作室温下芳族胺与α，β-不饱和化合物的氮杂-迈克尔反应的催化剂温度以高产率生产β-氨基化合物。催化剂可以重复使用几次，而不会明显降低催化活性。
• Synthesis of short and long-wavelength functionalised probes: amino acids' labelling and photophysical studies
  作者：Vânia H.J. Frade、Síria A. Barros、João C.V.P. Moura、Paulo J.G. Coutinho、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tet.2007.09.042

  日期：2007.12

  maximum emission wavelengths shifted to values higher than 644 nm. The synthesis of novel functionalised 5,9-diaminobenzo[a]phenoxazinium salts, by reaction of 5-ethylamino-4-methyl-2-nitrosophenol and N-substituted 1-naphthylamine and their use in the covalent labelling of the N or C terminals of valine, produced derivatives with long-wavelength emissions (644–653 nm). Photophysical studies using the

  以不同的方式对短和长波长在主链和侧链的N或C末端的α-氨基酸进行荧光标记。合成的N- [3-（萘-1-基氨基）丙酰基]氨基酸甲酯在电磁波谱的可见光区域（〜415 nm）表现出强荧光。这些化合物与5-二乙基氨基-2-亚硝基苯酚或5-乙基氨基-4-甲基-2-亚硝基苯酚缩合产生苯并[ a ]吩恶嗪衍生物，最大发射波长移至高于644 nm的值。通过5-乙基氨基-4-甲基-2-亚硝基苯酚与N的反应合成新型功能化的5,9-二氨基苯并[ a ]苯恶嗪鎓盐取代的1-萘胺及其在缬氨酸N或C末端的共价标记中的使用，产生了具有长波长发射（644–653 nm）的衍生物。使用合成的化合物在不同溶剂和受控pH中进行了光物理研究。还初步评估了阳离子多环杂环化合物在乙醇和水中在生理pH值下的光稳定性。
• Yao, Ri-Sheng; Jiang, Lai-En; Wu, Sheng-Hua, Asian Journal of Chemistry, 2011, vol. 23, # 9, p. 3792 - 3794
  作者：Yao, Ri-Sheng、Jiang, Lai-En、Wu, Sheng-Hua、Deng, Sheng-Song、Yang, Yang

  DOI：——

  日期：——
• Fluorescence derivatisation of amino acids in short and long-wavelengths
  作者：Vânia H.J. Frade、Síria A. Barros、João C.V.P. Moura、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tetlet.2007.03.070

  日期：2007.5

  3-(Naphthalen-1-ylamino)propanoic acid was coupled to the amino group of the main and lateral chains of various amino acids in order to evaluate its applicability as a fluorescent derivatising reagent. The resulting amino acid derivatives are strongly fluorescent with a maximum emission of about 415 run. Condensation of these derivatives with 5-ethylamino-4-methyl-2-nitrosophenol hydrochloride resulted in the corresponding blue benzo[a]phenoxazinium conjugates, also revealing strong fluorescence in ethanol and water at physiological pH and good quantum yields, but with emission wavelengths between 644 and 657 nm, which was preferable in biological assays. (c) 2007 Elsevier Ltd. All rights reserved.