2-甲氧基-4-苯基氨基甲基-苯酚 | 58285-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基-4-苯基氨基甲基-苯酚
• 英文名称: 4-anilinomethyl-2-methoxyphenol
• 英文别名: 4-(Anilinomethyl)-2-methoxy-phenol；4-(anilinomethyl)-2-methoxyphenol
• CAS: 58285-77-1
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: UKQLNPDOROJMTD-UHFFFAOYSA-N

物化性质

• 熔点：
  250 °C(Solv: methanol (67-56-1))
• 沸点：
  398.6±27.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基-4-苯基氨基甲基-苯酚 、 硫代异氰酸苯酯 以 氯仿 为溶剂， 以71%的产率得到1-(4-Hydroxy-3-methoxybenzyl)-1, 3-diphenylthiourea (1b)
  参考文献：
  名称：

  Synthesis and biological evaluation of novel N, N′-disubstituted urea and thiourea derivatives as potential anti-melanoma agents

  摘要：

  Two series of urea and thiourea derivatives (1a-11a, 1b-11b) have been synthesized; all the 22 compounds were reported for the first time. Their anti-proliferative activities against the melanoma cell line B16-F10 were evaluated. Among the compounds tested, compound 6b exhibited the most potent activity in melanoma cells growth inhibition (IC50 = 0.33 mu M). The bioassay tests showed that anti-proliferative activities of these novel compounds were possibly caused by inhibition of ERK1/2 phosphorylation level. Therefore, compound 6b can be a potential anti-melanoma agent and an inhibitor of ERK1/2 phosphorylation deserving further research.

  DOI：

  10.3109/14756366.2011.608665
• 作为产物：
  描述：

  N-(4-hydroxy-3-methoxybenzylidene)aniline 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-甲氧基-4-苯基氨基甲基-苯酚
  参考文献：
  名称：

  Synthesis and biological evaluation of novel N, N′-disubstituted urea and thiourea derivatives as potential anti-melanoma agents

  摘要：

  Two series of urea and thiourea derivatives (1a-11a, 1b-11b) have been synthesized; all the 22 compounds were reported for the first time. Their anti-proliferative activities against the melanoma cell line B16-F10 were evaluated. Among the compounds tested, compound 6b exhibited the most potent activity in melanoma cells growth inhibition (IC50 = 0.33 mu M). The bioassay tests showed that anti-proliferative activities of these novel compounds were possibly caused by inhibition of ERK1/2 phosphorylation level. Therefore, compound 6b can be a potential anti-melanoma agent and an inhibitor of ERK1/2 phosphorylation deserving further research.

  DOI：

  10.3109/14756366.2011.608665

文献信息

• Synthesis of an Fe–Pd bimetallic catalyst for <i>N</i>-alkylation of amines with alcohols <i>via</i> a hydrogen auto-transfer methodology
  作者：Peng-yu Wu、Guo-ping Lu、Chun Cai

  DOI：10.1039/d0gc03725g

  日期：——

  systems, and thus the exploration of a highly efficient and recyclable heterogeneous catalyst remains meaningful. In this work, a novel bimetallic catalyst, Fe10Pd1/NC500 derived from bimetallic MOF NH2-MIL-101(Fe10Pd1), has been prepared, and the catalyst exhibits superior catalytic performance for the N-alkylation of amines with alcohols via a hydrogen auto-transfer methodology. High yields of the

  从经济和环境的角度来看，结合脱氢，中间反应和氢化的氢自动转移（HAT）或借用氢（BH）方法被认为是一锅合成的绝佳策略。尽管已经为开发用于HAT反应的催化剂做出了很多努力，但是在大多数报道的催化系统中仍然需要苛刻的条件，外部碱或大量的贵金属，因此，探索一种高效且可回收的多相催化剂仍然有意义。在这项工作中，一种新型的双金属催化剂Fe 10 Pd 1 / NC500衍生自双金属MOF NH 2 -MIL-101（Fe 10 Pd 1），并且通过氢自动转移方法，该催化剂对胺与醇的N-烷基化表现出优异的催化性能。在120℃下，醇/胺的摩尔比为2∶1，不需要的外部添加剂或溶剂就可以得到高产率的所需产物。与单金属催化剂相比，观察到了催化性能的显着提高，这可以归因于双金属合金内部的“协同效应”。已经揭示出N掺杂的碳载体可提供必要的碱性，从而避免了对外部碱的需求。此外，Fe 10 Pd 1显示了宽的基材范围和出色的可重复使用性/
• Niobium Oxide Supported on Cubic Spinel Cobalt Oxide as an Efficient Heterogeneous Catalyst for the Synthesis of Imines via Dehydrogenative Coupling of Amines and Alcohols
  作者：Balasaheb D. Bankar、Krishnan Ravi、Saravanan Subramanian、Ankush V. Biradar

  DOI：10.1007/s10562-022-03943-2

  日期：2022.12

  results are confirmed further by PXRD d-spacing. Whereas cobalt oxide exists in (2 2 2), (3 1 1), and (1 1 1) facet, which confirms the crystal cubic spinel structure of Co3O4. The TPD ammonia desorption Nb2O5/Co3O4 result confirms the presence of 0.441 mmol/g acidic sites. The synthesized Nb2O5/Co3O4 catalyst effectively transformed aromatic amines and benzyl alcohols to imines through a dehydrogenative

  开发用于脱氢转化的可持续化学过程为选择性合成含氮化合物带来了可喜的结果。我们报道了使用共沉淀法合成 Nb 2 O 5 /Co 3 O 4催化剂，然后是水热法。FESEM、NH 3 -TPD、PXRD、FT-IR吡啶吸附研究和XPS用于表征合成材料的化学和结构性质。FESEM分析显示Nb均匀地分布在Co 3 O 4的表面上。3.3 wt% Nb 在 Co 3 O 4上显示出 (2 5 0) 和 (0 0 1) 晶面，并且这些结果通过 PXRD d-间距进一步证实。而氧化钴存在于(2 2 2)、(3 1 1)和(1 1 1)晶面，这证实了Co 3 O 4的晶体立方尖晶石结构。TPD 氨解吸 Nb 2 O 5 /Co 3 O 4结果证实存在 0.441 mmol/g 酸性位点。合成的Nb 2 O 5 /Co 3 O 4催化剂通过脱氢偶联反应有效地将芳香胺和苯甲醇转化为亚胺。3.3 wt% Nb 2
• Redox-Neutral Intramolecular Dearomative Spirocyclization of Phenols Induced by Visible Light
  作者：Linlin Zhang、Fengchi Hu、Lei Shen、Lijuan Gao、Yunhong Yang、Zhiqiang Pan、Chengfeng Xia

  DOI：10.1021/acs.orglett.3c01257

  日期：2023.5.5

  spirocyclohexadienone. Mechanistic experiments revealed that the aryl halide was reduced to aryl radical via the single-electron transfer (SET) process under visible light irradiation. The electrophilic addition of an aryl radical with the phenolate anion moiety gave a radical anion intermediate, which recycled the photocatalyst by a second SET process.

  本文描述的是由可见光诱导的氧化还原中性分子内脱芳环化。光化学环化由酚盐阴离子衍生的光催化剂催化，并产生螺环己二烯酮。机理实验表明，芳基卤化物在可见光照射下通过单电子转移 (SET) 过程还原为芳基自由基。芳基与酚盐阴离子部分的亲电加成产生自由基阴离子中间体，通过第二个 SET 过程回收光催化剂。
• A reusable MOF supported single-site nickel-catalyzed direct N-alkylation of anilines with alcohols
  作者：Yuanyuan Lu、Huining Chai、Kun Yu、Chaonan Huang、Yujie Li、Jinyu Wang、Jiping Ma、Weiqiang Tan、Guangyao Zhang

  DOI：10.1016/j.tet.2022.132993

  日期：2022.10

  The direct N-alkylation of amines with alcohols is an efficient route through a borrowing hydrogen (BH) strategy. Herein, a highly selective, and reusable Ni(II)-bipyridine-based metal-organic framework (MOF) catalyst was designed for this organic transformation. This earth-abundant metal-based metal-organic framework (MOF) catalyst significantly outperform their homogeneous analogues and the immobilized

  胺与醇的直接N-烷基化是通过借氢 (BH) 策略的有效途径。在此，为这种有机转化设计了一种高选择性、可重复使用的 Ni(II)-联吡啶基金属有机骨架 (MOF) 催化剂。这种富含地球的金属基金属有机骨架 (MOF) 催化剂显着优于其均相类似物，并且固定化催化剂可重复使用至少 4 个循环，而目标产物的产率不会显着降低。
• Rai, Mangat; Kumar, Surinder; Singh, Baldev, Journal of the Indian Chemical Society, 1982, vol. 59, # 1, p. 80 - 81
  作者：Rai, Mangat、Kumar, Surinder、Singh, Baldev、Krishan, Kewal、Singh, Ajit

  DOI：——

  日期：——