1-(4-吗啉基甲基)-2-萘酚 | 27438-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(4-吗啉基甲基)-2-萘酚
• 中文别名: 1-(吗啉甲基)-2-萘酚
• 英文名称: 2-hydroxy-1-(N-morpholinomethyl)naphthalene
• 英文别名: 1-(Morpholinomethyl)naphthol-(2)；1-(morpholinomethyl)naphthalen-2-ol；1-morpholinomethyl-2-naphthol；1-(N-morpholinomethyl)-2-naphthol；1-(N-morpholinyl)methyl-2-naphthol；1-(Morpholin-4-ylmethyl)-2-naphthol；1-(morpholin-4-ylmethyl)naphthalen-2-ol
• CAS: 27438-39-7
• 化学式: C₁₅H₁₇NO₂
• mdl: MFCD00021614
• 分子量: 243.305
• InChiKey: VNKDDFRRCCZWOU-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C
• 沸点：
  406.3±30.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)
• 溶解度：
  >36.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-(4-吗啉基甲基)-2-萘酚 在 氢氧化钾 、 镍 作用下， 生成 1-甲基萘-2-醇
  参考文献：
  名称：

  Mannich Compounds of 2-Naphthol Derivatives.

  摘要：

  研究了一些 2-萘酚及其四氢化合物的曼尼希反应。2-萘酚（I）与吗啉的曼尼希反应生成 1-（吗啉甲基）化合物（II），2-羟基-1-萘酸（V）也通过同样的反应得到了这种化合物。另一方面，2-四氢萘酚（XVI）通过曼尼希反应得到 3-（吗啉甲基）衍生物（XV）。2-Hydroxy-3-naphthoic acid (VI) 及其四氢化合物 (IX) 分别被引入 1-（吗啉甲基）衍生物 XVII 和 XIX。还研究了这些曼尼希化合物的一些转化过程。

  DOI：

  10.1248/cpb.12.112
• 作为产物：
  描述：

  4-methoxymethyl-morpholine 、 1,1-亚甲基-2-萘酚 以 苯 为溶剂， 生成 1-(4-吗啉基甲基)-2-萘酚
  参考文献：
  名称：

  A New Approach to the Synthesis of Phenol-Containing Macroheterocycles

  摘要：

  A one-step method for the synthesis of new phenol-containing cryptands and cryptohemispherands by treating N,N'-bis(methoxymethyl)diazacrowns with the appropriate bis- and trisphenols is reported. This method, based on a special Mannich reaction, gives cyclized products without-the need for protecting groups and high dilution conditions. Unusually high yields of cryptohemisherands were realized using a relatively high concentration of the starting materials (50 mmol/L) and in the absence of metal cations as template agents in the reaction mixture. These excellent yields can be explained by intramolecular hydrogen bonding which prevents polycondensation. This new method also allowed preparation of new phenol-containing cylindrical tricyclic ligands by first forming bisphenol-substituted diaza-18-crown-6 at 80 degrees C followed by its reaction with a second bis(methoxymethyl)-substituted diaza-18-crown-6 at 144 degrees C. Crystal structures of two cryptohemispherands are reported herein. A shorter internal distance between N and O atoms in 27 as compared to 6 (R = NO2, n = m = 2) indicates intramolecular hydrogen bonding in phenol-containing macrocycle 27.

  DOI：

  10.1021/jo00120a040

文献信息

• Cu(II)-Catalyzed <i>ortho</i>-Selective Aminomethylation of Phenols
  作者：Jin-Ling Dai、Nan-Qi Shao、Jin Zhang、Run-Ping Jia、Dong-Hui Wang

  DOI：10.1021/jacs.7b06785

  日期：2017.9.13

  A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2-Csp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical

  已经开发出一种 Cu(II) 催化的游离酚与三氟硼酸盐的邻位选择性官能化，以在温和条件下提供 Csp2-Csp3 偶联产物。发现苯酚和氨基甲基三氟硼酸钾底物上的各种官能团是相容的，以中等至极好的收率提供相应的产品。提出了一种涉及六元过渡态的单电子转移自由基偶联机制，以合理化反应中的高水平邻位选择性。该协议提供了对邻氨基甲基取代酚、非天然氨基酸和其他生物活性小分子的直接访问。
• Synthesis of unsymmetrical dinucleating ligands bearing nitrogen and oxygen donor atoms
  作者：David E. Fenton、George Papageorgiou

  DOI：10.1016/0040-4020(96)00222-0

  日期：1996.4

  The synthesis of unsymmetrical dinucleating ligands bearing nitrogen and oxygen donor atoms is described. The Schiff-base condensation of functionalised salicylaldehyde derivatives with primary amines gave rise to unsymmetrical unsaturated ligands, whereas condensation with secondary amines followed by in situ reduction of the iminium species with sodium borohydride, led to the formation of unsymmetrical

  描述了带有氮和氧供体原子的不对称双核配体的合成。功能化水杨醛衍生物与伯胺的席夫碱缩合产生不对称的不饱和配体，而与仲胺的缩合随后用硼氢化钠原位还原亚胺类，导致形成不对称的饱和配体。后者也通过4-氯间苯二酚的曼尼希串联反应制备。
• Novel synthesis of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans
  作者：Po-Jung Jimmy Huang、T. Stanley Cameron、Amitabh Jha

  DOI：10.1016/j.tetlet.2008.10.083

  日期：2009.1

  (retro-aldol product). This Mannich base then disproportionates into a quinone methide intermediate and the secondary amine is regenerated. It then forms an enamine intermediate with 2,2-dialkylacetaldehyde (another retro-aldol product). Finally, the quinone methide intermediate undergoes electrocyclic ring closure with enamines to produce the title compounds.

  由2-萘酚，仲胺和3-羟基-2,2-二烷基丙醛制备2,2-二烷基-3-二烷基氨基-2,3-二氢-1 H-萘并[ 2,1- b ]吡喃。催化量p的存在-甲苯磺酸。该一锅法反应涉及3-羟基-2,2-二烷基丙醛的逆醛醇缩合，然后由2-萘酚，仲胺和甲醛（逆醛醇产物）形成曼尼希碱中间体。然后，该曼尼希碱歧化成醌甲基化物中间体，并再生仲胺。然后，它与2，2-二烷基乙醛（另一种逆醛醇产物）形成烯胺中间体。最后，醌甲基化物中间体与烯胺经历电环闭合以产生标题化合物。
• Reaction of Push–Pull Enaminoketones and <i>in Situ</i> Generated <i>ortho</i>-Quinone Methides: Synthesis of 3-Acyl-4<i>H</i>-chromenes and 2-Acyl-1<i>H</i>-benzo[<i>f</i>]chromenes as Precursors for Hydroxybenzylated Heterocycles
  作者：Anton V. Lukashenko、Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.6b02716

  日期：2017.2.3

  developed. The chromenes are presumably formed through an initial oxa-Diels–Alder reaction, followed by an elimination of amine. The possibility of further transformations of given chromenes to o-hydroxybenzylated pyrazoles, isoxazoles, and pyridines has been demonstrated.

  已经开发了一种简单有效的方法，可以由邻醌甲基化物前体和推挽式烯酮合成吡喃环中含有三氟乙酰基或芳酰基的4 H-苯二甲基和1 H-苯并[ f ]苯二甲基。苯并二氢吡喃酮可能是通过最初的Oxa-Diels-Alder反应形成，然后消除胺而形成的。已经证明给定的色烯进一步转化为邻羟基苄基化的吡唑，异恶唑和吡啶的可能性。
• Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block
  作者：Matthias Mastalir、Ernst Pittenauer、Günter Allmaier、Karl Kirchner

  DOI：10.1021/jacs.7b05253

  日期：2017.7.5

  well-defined hydride Mn(I) PNP pincer complex, recently developed in our laboratory, catalyzes this process in a very efficient way, and a total of 28 different aminomethylated products were synthesized and isolated yields of up to 91%. In a preliminary study, a related Fe(II) PNP pincer complex was shown to catalyze the methylation of 2-naphtol rather than its aminomethylation displaying again the divergent

  该研究代表了锰催化的环境良性、实用的三组分氨甲基化活化芳香化合物的第一个例子，包括萘酚、苯酚、吡啶、吲哚、咔唑和噻吩，结合胺和甲醇作为 C1 源。这些反应通过一系列脱氢和缩合步骤以高原子效率进行，从而产生选择性的 CC 和 CN 键形成，从而释放氢和水。我们实验室最近开发了一种明确定义的氢化物 Mn(I) PNP 钳形复合物，以非常有效的方式催化了这一过程，总共合成了 28 种不同的氨甲基化产物，分离产率高达 91%。在初步研究中，