3,5-dimethoxy-N-(4-methoxybenzyl)aniline | 134054-81-2

• 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: 3,5-dimethoxy-N-(4-methoxybenzyl)aniline
• 英文别名: N-(4-methoxybenzyl)-3,5-dimethoxybenzeneamine；N-(4-Methoxybenzyl)-3,5-dimethoxyaniline；3,5-dimethoxy-N-[(4-methoxyphenyl)methyl]aniline
• CAS: 134054-81-2
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: URDGSWSJNMUJLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxy-N-(4-methoxybenzyl)aniline 、 对苯醌 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以58%的产率得到5,7-dimethoxy-9-(4-methoxybenzyl)-9H-carbazol-3-ol
  参考文献：
  名称：

  通过富电子苯胺和醌的单步合成3-羟基咔唑

  摘要：

  在室温下，通过在PhMe / AcOH（4：1）中富电子苯胺和醌的环化反应，可以一步合成3-羟基咔唑。这种化学方法可以耐受各种取代的苯醌和萘醌，但是对苯胺的电子和空间特性均敏感。所需的3-羟基咔唑衍生物通常以中等收率生产。

  DOI：

  10.1016/j.tetlet.2016.11.009
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3,5-dimethoxy-N-(4-methoxybenzyl)aniline
  参考文献：
  名称：

  Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization

  摘要：

  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.

  DOI：

  10.1021/jm00112a036

文献信息

• Electrophile-Induced Dearomatizing Spirocyclization of <i>N</i>-Arylisonicotinamides: A Route to Spirocyclic Piperidines
  作者：Gareth Arnott、Heloise Brice、Jonathan Clayden、Emma Blaney

  DOI：10.1021/ol801092s

  日期：2008.7.17

  Treatment of N-arylisonicotinamides with trifluoromethanesulfonic anhydride triggers intramolecular nucleophilic attack of the aryl ring on the 4-position of the pyridinium intermediate. The products are spirocyclic dihydropyridines which can be converted to valuable spirocyclic piperidines related to biologically active molecules such as MK-677.
• 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.
• Single-step synthesis of 3-hydroxycarbazoles by annulation of electron-rich anilines and quinones
  作者：Eugenia Pushkarskaya、Brian Wong、Chong Han、Simona Capomolla、Chunang Gu、Brian M. Stoltz、Haiming Zhang

  DOI：10.1016/j.tetlet.2016.11.009

  日期：2016.12

  A single-step synthesis of 3-hydroxycarbazoles has been achieved via annulation of electron-rich anilines and quinones in PhMe/AcOH (4:1) at room temperature. This chemistry tolerates various substituted benzoquinones and naphthoquinones, however, is sensitive to both the electronic and steric properties of the anilines. The desired 3-hydroxycarbazole derivatives are generally produced in moderate

  在室温下，通过在PhMe / AcOH（4：1）中富电子苯胺和醌的环化反应，可以一步合成3-羟基咔唑。这种化学方法可以耐受各种取代的苯醌和萘醌，但是对苯胺的电子和空间特性均敏感。所需的3-羟基咔唑衍生物通常以中等收率生产。