4-methoxy-N-(3,4,5-trimethoxybenzyl)aniline | 134029-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-N-(3,4,5-trimethoxybenzyl)aniline
• 英文别名: 4-methoxy-N-[(3,4,5-trimethoxyphenyl)methyl]aniline
• CAS: 134029-85-9
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: VZXKFUZYRHTORS-UHFFFAOYSA-N

物化性质

• 沸点：
  438.0±45.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(3,4,5-trimethoxybenzyl)aniline 、 4-methyl-N-(3,4,5-trimethoxybenzyl)aniline hydrochloride 以gave 110c (8.14 g, 80.7%) as tiny white crystals的产率得到4-methoxy-N-(3,4,5-trimethoxybenzyl)aniline hydrochloride
  参考文献：
  名称：

  Stilbene derivatives as anticancer agents

  摘要：

  本发明涉及一种具有抗癌作用的苯乙烯衍生物。该化合物可用于治疗易受其治疗的癌症，并可用于治疗此类癌症的方法。本发明还揭示了含有该化合物的制药组合物。在所披露的化合物中，有三种优选化合物，分别为（Z）-1-（4-甲氧基苯基）-2-（3,4,5-三甲氧基苯基）乙烯，（Z）-1-（4-甲基苯基）-2-（3,4,5-三甲氧基苯基）乙烯和4-甲基-3'，4'，5'-三甲氧基苯乙胺盐酸盐。

  公开号：

  US05430062A1
• 作为产物：
  描述：

  4-methoxy-N-(3,4,5-trimethoxybenzylidene)aniline 在 苯硅烷 、 C₄₃H₄₄FeN₂O₄ 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以145 mg的产率得到4-methoxy-N-(3,4,5-trimethoxybenzyl)aniline
  参考文献：
  名称：

  一种高效的基础金属催化剂：使用异常的NHC–Fe（0）配合物将胺化学选择性还原成胺

  摘要：

  A base-metal, Fe(0)-catalyzed hydrosilylation of imines to obtain amines is reported here which outperforms its noble-metal congeners with the highest TON of 17000. The catalyst, (aNHC)Fe(CO)(4), works under very mild conditions, with extremely low catalyst loading (down to 0.005 mol %), and exhibits excellent chemoselectivity. The facile nature of the imine reduction under mild conditions has been further demonstrated by reducing imines towards expensive commercial amines and biologically important N-alkylated sugars, which are difficult to achieve otherwise. A mechanistic pathway and the source of chemoselectivity for imine hydrosilylation have been proposed on the basis of the well-defined catalyst and isolable intermediates along the catalytic cycle.

  DOI：

  10.1021/acs.organomet.6b00478

文献信息

• Aluminum Metal–Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis
  作者：Neha Antil、Ajay Kumar、Naved Akhtar、Rajashree Newar、Wahida Begum、Ashutosh Dwivedi、Kuntal Manna

  DOI：10.1021/acscatal.0c04379

  日期：2021.4.2

  and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal–organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under

  化学选择性的和非均质的富含地球的金属催化剂的开发对于环境友好的化学合成至关重要。我们报告了一种高效，化学选择性和可重复使用的单中心氢化镍（II）氢化物催化剂，该催化剂基于坚固且多孔的铝金属有机骨架（MOFs）（DUT-5），用于将硝基和腈化合物加氢成相应的胺并进行氢解温和条件下制备芳基醚。镍-氢化物催化剂的制备是通过的氢氧化铝次级结构单元的金属化的Al具有（μ的式DUT-5的（事业部）2 -OH）（BPDC）（BPDC = 4,4'-联苯双酯）与NIBR 2然后与NaEt 3反应BH。DUT-5-NiH具有广泛的底物范围，在1 bar H 2下氢化芳族和脂肪族硝基和腈化合物时，具有出色的官能团耐受性至少可以回收再利用10次。通过改变腈氢化的反应条件，还选择性地提供了对称或不对称的仲胺。实验和计算研究表明，在营业额限制步骤中，镍与镍的可逆腈配位是可逆的，然后将1,2-的配位腈插入氢化镍中。此
• Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of Primary Amines
  作者：Pandula T. Kirinde Arachchige、Hanbin Lee、Chae S. Yi

  DOI：10.1021/acs.joc.8b00649

  日期：2018.5.4

  found to be effective for the direct deaminative coupling of two primary amines to form secondary amines. The catalyst 1/L1 was highly chemoselective for promoting the coupling of two different primary amines to afford unsymmetric secondary amines. The analogous coupling of aniline with primary amines formed aryl-substituted secondary amines. The treatment of aniline-d7 with 4-methoxybenzylamine led to

  从四核Ru-H与邻苯二酚配体（1 / L1）配合物原位生成的催化体系被发现对于两个伯胺的直接脱氨反应形成仲胺是有效的。催化剂1 / L1具有高度化学选择性，可促进两种不同伯胺的偶联，从而获得不对称仲胺。苯胺与伯胺的类似偶联形成芳基取代的仲胺。用4-甲氧基苄胺处理苯胺-d 7导致偶联产物在CH 2上具有明显的氘掺入（18％D）。在从4-甲氧基苄胺的偶联反应中分离出的产物的α-碳上观察到最明显的碳同位素效应（C（1）= 1.015（2））。通过测量4-甲氧基苯胺与一系列对位取代的苄胺4-XC 6 H 4 CH 2 NH 2（X = OMe，Me，H，F，CF 3）的偶联反应速率来构建Hammett图（ ρ= −0.79±0.1）。基于这些结果，提出了一种可行的偶联反应机理。催化偶联方法提供了操作上简单且化学选择性的仲胺产物合成，而无需使用任何反应性试剂或形成浪费的副产物。
• An Ullmann Coupling of Aryl Iodides and Amines Using an Air-Stable Diazaphospholane Ligand
  作者：Minghua Yang、Fei Liu

  DOI：10.1021/jo0712291

  日期：2007.11.1

  A copper-based catalytic system, using an air-stable diazaphospholane as the ligand, was developed for an efficient Ullmann reaction between aryl iodides and alkyl or heterocyclic amines.

  为了使芳基碘化物与烷基或杂环胺发生有效的乌尔曼反应，开发了一种使用空气稳定的二氮杂膦烷作为配体的铜基催化体系。
• One-pot stepwise reductive amination reaction by <i>N</i> -coordinate sulfonamido-functionalized Ru(II) complexes in water
  作者：Nilgün Kayacı、Serkan Dayan、Namık Özdemir、Osman Dayan、Nilgün Kalaycıoğlu Özpozan

  DOI：10.1002/aoc.4558

  日期：2018.12

  New complexes of formula [RuCl(p‐cymene)(L)] (7–12) were prepared with [RuCl2(p‐cymene)]2 and pre‐synthesized N‐arenesulfonly‐o‐phenylenediamines (1–6) and characterized using 1H NMR, 13C NMR, Fourier transform infrared and UV–visible spectroscopic techniques, and single‐crystal X‐ray diffraction analysis was performed for one complex (8). Complexes 7–12 were investigated in the reduced imine synthesis

  式的新的复合物将[RuCl（p -cymene）（L）]（7 - 12）用制备将[RuCl 2（p -cymene）] 2和预合成Ñ -arenesulfonly- ø苯二胺（1 - 6）和用1 H NMR，13 C NMR，傅立叶变换红外和紫外可见光谱技术进行表征，并对一种配合物进行了单晶X射线衍射分析（8）。配合物7 – 12在还原的亚胺合成反应中（在HCOONa / HCOOH存在下）进行了研究。发现最好的周转频率值是100 [ - 1为1和99ħ -1为6在4-甲氧基苯胺和3,4,5-三甲氧基苯的转移hydrogenative还原胺化反应。该反应的最重要特征是由于其在水性环境中进行，因此是一种环境友好的方法。没有使用有机溶剂，可以说这一反应代表了绿色化学。
• Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Asit K. Chakraborti、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00112a036

  日期：1991.8

  An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in the five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Several cis-stilbenes, structurally similar to combretastatins, were highly cytotoxic in all five cell lines and these were also found to be active as inhibitors of tubulin polymerization. The most active compounds also inhibited the binding of colchicine to tubulin. The most potent of the new compounds, both as a tubulin polymerization inhibitor and as a cytotoxic agent, was (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene (5a). This substance was almost as potent as combretastatin A-4 (1a), the most active of the combretastatins, as a tubulin polymerization inhibitor. Compound 5a was found to be approximately 140 times more cytotoxic against HT-29 colon adenocarcinoma cells and about 10 times more cytotoxic against MCF-7 breast carcinoma cells than combretastatin A-4. However, 5a was found to be about 20 times less cytotoxic against A-549 lung carcinoma cells, 30 times less cytotoxic against SKMEL-5 melanoma cells, and 7 times less cytotoxic against MLM melanoma cells than combretastatin A-4. The relative potencies 5a > 8a > 6a for the cis, dihydro, and trans compounds, respectively, as inhibitors of tubulin polymerization are in agreement with the relative potencies previously observed for combretastatin A-4 (1a), dihydrocombretastatin A-4 (1c), and trans-combretastatin A-4 (1b). The relative potencies 5a > 8a > 6a were also reflected in the results of the cytotoxicity assays. Structure-activity relationships of this group of compounds are also discussed.