1-amino-4,5-bis(dimethylamino)naphthalene | 199342-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-amino-4,5-bis(dimethylamino)naphthalene
• 英文别名: 4-amino-1,8-bis(dimethylamino)naphthalene；4-N,4-N,5-N,5-N-tetramethylnaphthalene-1,4,5-triamine
• CAS: 199342-45-5
• 化学式: C₁₄H₁₉N₃
• 分子量: 229.325
• InChiKey: SVYQPYQJDKNEPW-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-amino-4,5-bis(dimethylamino)naphthalene 在 ammonium hydroxide 、 水 作用下， 以 乙腈 为溶剂， 反应 73.0h， 生成
  参考文献：
  名称：

  α-Amino acid-assisted autoxidation of naphthalene proton sponge affording 1,4-naphthoquinone nitrogen derivatives

  摘要：

  DOI：

  10.1016/j.mencom.2023.02.015
• 作为产物：
  描述：

  1,8-bis(dimethylamino)-4-nitronaphthalene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 2.0h， 以100%的产率得到1-amino-4,5-bis(dimethylamino)naphthalene
  参考文献：
  名称：

  Immobilized Proton Sponge on Inorganic CarriersThe Synergic Effect of the Support on Catalytic Activity

  摘要：

  DOI：

  10.1016/s0021-9517(02)93692-4

文献信息

• Aryl diazonium nanomagnetic sulfate and potassium iodide: an iodination process
  作者：Eskandar Kolvari、Ali Amoozadeh、Nadiya Koukabi、Somayeh Otokesh、Mohsen Isari

  DOI：10.1016/j.tetlet.2014.02.073

  日期：2014.7

  procedure for the synthesis of iodoarenes is developed which involves the sequential diazotization–iodination of aromatic amines with sodium nitrite, nanomagnetic supported sulfonic acid, and potassium iodide under solvent-free conditions at room temperature.

  开发了一种简单高效的碘代芳烃合成方法，该方法涉及在无溶剂条件下于室温下用亚硝酸钠，纳米磁性负载的磺酸和碘化钾对芳族胺进行连续重氮化-碘化。
• A Simple and Effective Procedure for theN-Permethylation of Amino-Substituted Naphthalenes
  作者：Vladimir I. Sorokin、Valery A. Ozeryanskii、Alexander F. Pozharskii

  DOI：10.1002/ejoc.200390085

  日期：2003.2

  ohols) with good to excellent yields. Steric hindrance does not prevent the reaction. Some amines with electron-withdrawing groups, especially at nonconjugated positions, are also alkylated. The procedure allows the combination of a reduction (catalytic or by tin dichloride in acidic media) and a methylation in a one-pot process. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  多种氨基取代的萘可以通过 Me2SO4/Na2CO3/H2O（醇）系统进行 N-全甲基化，收率非常好。空间位阻不会阻止反应。一些带有吸电子基团的胺，特别是在非共轭位置，也被烷基化。该程序允许在一锅法中将还原（催化或通过酸性介质中的二氯化锡）和甲基化相结合。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Novel Polyfunctional Tautomeric Systems Containing Salicylideneamino and Proton Sponge Moieties
  作者：Valery A. Ozeryanskii、Alexander F. Pozharskii、Wojciech Schilf、Bohdan Kamieński、Wanda Sawka-Dobrowolska、Lucjan Sobczyk、Eugeniusz Grech

  DOI：10.1002/ejoc.200500574

  日期：2006.2

  In the case of 7, proton transfer to the imine nitrogen atom occurs in the solid state, accompanied by a remarkable shortening of the OHN bridge (2.553 A). In dinitro derivative 8, the OH proton jumps to the dimethylamino groups, giving a new tautomeric form with the formation of a homoconjugated [NHN]+ cation. Protonation of 6 and 7, affecting the (dimethylamino)naphthyl moiety, disrupts the π-coupling

  已经合成了第一个含有带有 5'-溴 (6)、5'-硝基 (7) 和 3',5'-二硝基 (8) 取代基的质子海绵残基的水杨基芳胺。X 射线衍射和 1H、13C 和 15N NMR 和红外光谱表明，6 和 7 包含非常强的邻羟基席夫碱典型的 OHN 桥。与二甲氨基萘基环的额外 π 电子耦合体现在几何和红外参数中。在 7 的情况下，质子转移到亚胺氮原子发生在固态，伴随着 OHN 桥的显着缩短 (2.553 A)。在二硝基衍生物 8 中，OH 质子跃迁到二甲氨基，形成新的互变异构形式，形成同共轭 [NHN]+ 阳离子。6 和 7 的质子化，影响（二甲氨基）萘基部分，破坏 π 偶联并使这些分子与常见的芳香席夫碱不同，对水解高度敏感，而 8 已经自质子化，在湿 DMSO 中与相应的水杨醛和芳胺在大约 10 小时内达到平衡。室温下为 1:1 比例。（© Wiley-VCH Verlag GmbH & Co
• Magnetic Superbasic Proton Sponges Are Readily Removed and Permit Direct Product Isolation
  作者：Elia M. Schneider、Renzo A. Raso、Corinne J. Hofer、Martin Zeltner、Robert D. Stettler、Samuel C. Hess、Robert N. Grass、Wendelin J. Stark

  DOI：10.1021/jo501913z

  日期：2014.11.21

  Workup in organic synthesis can be very time-consuming, particularly when using reagents with both a solubility similar to that of the desired products and a tendency not to crystallize. In this respect, reactions involving organic bases would strongly benefit from a tremendously simplified separation process. Therefore, we synthesized a derivative of the superbasic proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) and covalently linked it to the strongest currently available nanomagnets based on carbon-coated cobalt metal nanoparticles. The immobilized magnetic superbase reagent was tested in Knoevenagel- and ClaisenSchmidt-type condensations and showed conversions of up to 99%. High yields of up to 97% isolated product could be obtained by simple recrystallization without using column chromatography. Recycling the catalyst was simple and fast with an insignificant decrease in catalytic activity.
• A proton sponge-based fluorescent switch
  作者：Yi Xiao、Meiyan Fu、Xuhong Qian、Jingnan Cui

  DOI：10.1016/j.tetlet.2005.07.050

  日期：2005.9

  A proton-triggered fluorescent switch was developed through direct connection of a proton sponge, 1,8-bis(dimethyl-amino) naphthalene to a fluorophore, 4-aminonaphthalimide. The molecular fluorescent switch was based on a photoinduced electron transfer (PET) mechanism. The fluorescent switch exhibited significant fluorescence enhancement upon binding the lowconcentration protons in high pH aqueous solution. The high pK(a) value (around 11) of the fluorescent switch could be ascribed to the nature of the proton sponge. (c) 2005 Elsevier Ltd. All rights reserved.