6-Dimethylamino-<2>naphthoesaeure-methylester | 5043-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-Dimethylamino-<2>naphthoesaeure-methylester
• 英文别名: Methyl 6-(dimethylamino)-2-naphthoate；methyl 6-(dimethylamino)naphthalene-2-carboxylate
• CAS: 5043-06-1
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: YNDOGGZQRKTTKV-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149.5 °C
• 沸点：
  374.5±17.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  6-Dimethylamino-<2>naphthoesaeure-methylester 在 正丁基锂 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 生成
  参考文献：
  名称：

  Longer-Wavelength-Absorbing, Extended Chalcogenorhodamine Dyes

  摘要：

  Extended rhodamines were prepared by inserting an additional fused benzene ring into the rhodamine xanthylium core. The synthesis of "bent" dyes 4-E (E = S, Se, Te) began with regioselective lithiation of the 1-position of N,N-diisopropyl 6-dimethylamino-2-naphthamide (11b) with n-BuLi/TMEDA (>= 25:1 1- vs 3-lithiation) followed by addition of a dichalcogenide electrophile. The synthesis of "linear" dyes 5-E (E = S, Se, Te) began with regioselective lithiation of the 3-position of N,N-diethyl 6-dimethylamino-2-naphthamide (11a) with lithium tetramethylpiperidide (>= 50:1 3- vs 1-lithiation) followed by addition of a dichalcogenide electrophile. Dyes 4-E and 5-E have absorption maxima in the 633-700 nm range. Dyes 4-E generate singlet oxygen upon irradiation while dyes 4-S and 5-S are highly fluorescent, with quantum yields for fluorescence of 0.47 and 0.18, respectively. DFT calculations were performed on the 4-E and 5-E chromophores. For the dyes 4-E, the lowest energy excitation is due solely to the HOMO-LUMO transition. For dyes 5-E, the lowest energy excitation is a combination of two excitations, both having contributions from the HOMO to LUMO and HOMO-1 to LUMO.

  DOI：

  10.1021/acs.organomet.6b00255
• 作为产物：
  描述：

  6-氨基-2-萘酸 、 碘甲烷 在 sodium carbonate 、 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以99%的产率得到6-Dimethylamino-<2>naphthoesaeure-methylester
  参考文献：
  名称：

  Longer-Wavelength-Absorbing, Extended Chalcogenorhodamine Dyes

  摘要：

  Extended rhodamines were prepared by inserting an additional fused benzene ring into the rhodamine xanthylium core. The synthesis of "bent" dyes 4-E (E = S, Se, Te) began with regioselective lithiation of the 1-position of N,N-diisopropyl 6-dimethylamino-2-naphthamide (11b) with n-BuLi/TMEDA (>= 25:1 1- vs 3-lithiation) followed by addition of a dichalcogenide electrophile. The synthesis of "linear" dyes 5-E (E = S, Se, Te) began with regioselective lithiation of the 3-position of N,N-diethyl 6-dimethylamino-2-naphthamide (11a) with lithium tetramethylpiperidide (>= 50:1 3- vs 1-lithiation) followed by addition of a dichalcogenide electrophile. Dyes 4-E and 5-E have absorption maxima in the 633-700 nm range. Dyes 4-E generate singlet oxygen upon irradiation while dyes 4-S and 5-S are highly fluorescent, with quantum yields for fluorescence of 0.47 and 0.18, respectively. DFT calculations were performed on the 4-E and 5-E chromophores. For the dyes 4-E, the lowest energy excitation is due solely to the HOMO-LUMO transition. For dyes 5-E, the lowest energy excitation is a combination of two excitations, both having contributions from the HOMO to LUMO and HOMO-1 to LUMO.

  DOI：

  10.1021/acs.organomet.6b00255

文献信息

• Difluoroboron β-diketonate dye with intense red/near-infrared fluorescence in solutions and solid states
  作者：Nan Liu、Peng-Zhong Chen、Jian-Xin Wang、Li-Ya Niu、Qing-Zheng Yang

  DOI：10.1016/j.cclet.2019.04.058

  日期：2019.11

  β-diketonate (BF2bdk) complexes have attracted much attention due to their outstanding photophysical properties. However, BF2bdk with near-infrared fluorescence usually suffer from emission quenching in solid state due to the π–π stacking in aggregation. Herein, we report a BF2bdk dye exhibiting donor-acceptor (D-A) structure with the difluoroboron moiety acting as the electron acceptor and the aminonaphthalene

  摘要β-二酮硼酸二氟硼（BF2bdk）配合物因其出色的光物理性质而备受关注。但是，由于π-π聚集在一起，具有近红外荧光的BF2bdk通常遭受固态发射猝灭。在本文中，我们报道了一种BF2bdk染料，表现出供体-受体（DA）结构，其中二氟硼部分充当电子受体，氨基萘作为电子供体。它在溶液和聚集体中的红色/近红外区域都具有强烈的摩尔消光系数，大斯托克斯位移和强荧光。它用于活细胞的近红外成像。
• Discovery of a Sensitive, Selective, and Tightly Binding Fluorogenic Substrate of Bovine Plasma Amine Oxidase
  作者：Ke-Qing Ling、Lawrence M. Sayre

  DOI：10.1021/jo8018945

  日期：2009.1.2

  We report a novel fluorogenic substrate of bovine plasma amine oxidase (BPAO), namely, (2-(6-(aminomethyl)naphthalen-2-yloxy)ethyl)trimethylammonium (ANETA), which displays extremely tight binding to BPAO (Km 183 ± 14 nM) and yet is metabolized fairly quickly (kcat 0.690 ± 0.010 s−1), with the aldehyde turnover product (2-(6-formylnaphthalen-2-yloxy)ethyl)trimethylammonium serving as a real time reporting

  我们报告了牛血浆胺氧化酶 (BPAO) 的一种新型荧光底物，即 (2-(6-(氨基甲基)萘-2-基氧基)乙基)三甲基铵 (ANETA)，它与 ​​BPAO ( K m 183 ± 14 nM) 并且代谢相当快 ( k cat 0.690 ± 0.010 s -1），醛转换产物（2-（6-甲酰基萘-2-基氧基）乙基）三甲基铵作为酶活性的实时报告荧光团。这允许开发比分光光度法苄胺检测灵敏度高 2 个数量级的荧光非耦合检测。ANETA 的发现涉及通过基于结构的设计精心设计先导化合物 6-甲氧基-2-萘甲胺，该设计将 BPAO 的辅助阳离子结合位点视为控制结合亲和力的最重要的结构特征。基于结构的设计进一步确保了高选择性：ANETA 是 BPAO 的良好底物，但不是猪肾二胺氧化酶 (pkDAO) 或大鼠肝单胺氧化酶 (MAO-B) 的底物。ANETA 代表了第一个高度敏感、选择性、直接实时了解酶活性。
• Convenient Synthesis of <i>p</i>-Aminobenzoic Acids and their Methyl Esters
  作者：Marek Pietrzak、Beata Jędrzejewska、Dorota Mądrzejewska、Agnieszka Bajorek

  DOI：10.1080/00304948.2017.1260396

  日期：2017.1.2

  derivatives of benzoic acid was provided. Our need of various p-aminobenzoic acids and their esters for the preparation of a few boron-dipyrromethene (BODIPY) dyes, and other dyes containing difluoroborane moiety as spectroscopic probes prompted us to re-investigate and modify the reaction reported by Ott and his group nearly fifty years ago after our unsuccessful attempts to obtain these acids in good yields

  氨基具有重要的生物学和工业重要性，因为它们是生物体和氨基酸的基本组成部分。胺的性质取决于氮上取代基的类型、空间位阻和溶剂化效应。通常，胺的碱性随着胺上烷基数量的增加而增加，而芳基取代基通常使孤对电子离域进入环，导致碱性降低。这些因素可能导致氨基对此类化合物的光谱和氧化还原性质以及发生分子间和分子内电子转移 (ICT) 过程的可能性产生重大影响。芳香胺通常毒性很大，很容易通过皮肤吸收，有些是强致癌物。然而，对它们的结构进行适当的修改，可以得到具有所需特性的化合物，例如生物活性化合物、聚合物、自由基光引发剂、染料、光伏电池、发光二极管、光谱探针、现代医学技术和许多其他领域领域。对氨基苯甲醛是制备各种胺的方便且常用的起始试剂。Babu 和 Balasubramaniam 提出了一种通过醛氧化合成对二甲氨基苯甲酸的简单方法。然而，它需要亚氯酸钠，亚氯酸钠是危险的，而且不太普遍。而且，该方法与使用过
• Longer-Wavelength-Absorbing, Extended Chalcogenorhodamine Dyes
  作者：Mark W. Kryman、Theresa M. McCormick、Michael R. Detty

  DOI：10.1021/acs.organomet.6b00255

  日期：2016.6.13

  Extended rhodamines were prepared by inserting an additional fused benzene ring into the rhodamine xanthylium core. The synthesis of "bent" dyes 4-E (E = S, Se, Te) began with regioselective lithiation of the 1-position of N,N-diisopropyl 6-dimethylamino-2-naphthamide (11b) with n-BuLi/TMEDA (>= 25:1 1- vs 3-lithiation) followed by addition of a dichalcogenide electrophile. The synthesis of "linear" dyes 5-E (E = S, Se, Te) began with regioselective lithiation of the 3-position of N,N-diethyl 6-dimethylamino-2-naphthamide (11a) with lithium tetramethylpiperidide (>= 50:1 3- vs 1-lithiation) followed by addition of a dichalcogenide electrophile. Dyes 4-E and 5-E have absorption maxima in the 633-700 nm range. Dyes 4-E generate singlet oxygen upon irradiation while dyes 4-S and 5-S are highly fluorescent, with quantum yields for fluorescence of 0.47 and 0.18, respectively. DFT calculations were performed on the 4-E and 5-E chromophores. For the dyes 4-E, the lowest energy excitation is due solely to the HOMO-LUMO transition. For dyes 5-E, the lowest energy excitation is a combination of two excitations, both having contributions from the HOMO to LUMO and HOMO-1 to LUMO.