N-(4-methoxybenzylidene)octan-1-amine | 20172-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxybenzylidene)octan-1-amine
• 英文别名: (4-methoxy-benzylidene)-octyl-amine；p-Methoxybenzylidene-octyl-amine；1-(4-methoxyphenyl)-N-octylmethanimine
• CAS: 20172-76-3
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: FERXSVGPUVMBKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzylidene)octan-1-amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以0.651 g的产率得到[(4-methoxyphenyl)methyl]octylamine
  参考文献：
  名称：

  Antiparasitic activity of new gibbilimbol analogues and SAR analysis through efficiency and statistical methods

  摘要：

  Chagas' disease and leishmaniasis are parasitic infections enrolled among the neglected tropical diseases, which urge for new treatments. In the search for new chemical entities as prototypes, gibbilimbols A/B have shown antiparasitic activity against Trypanosoma cruzi and Leishmania infantum, and then a set of analogues (LINS03 series) of this natural product were synthesized and evaluated in vitro against the parasites. In the present paper we reported five new compounds with activity against these protozoan parasites, and quite low cytotoxicity. Moreover, the interference of plasma membrane permeability of these analogues were also evaluated. We found that [(4-methoxyphenyl) methyl] octylamine (4) was noteworthy due to its high activity against the amastigote form of both parasites (IC50 1.3-5.8 mu M) and good selectivity index. In order to unveil the SAR for this chemotype, we also presented a group efficiency analysis and PCA and HCA study, which indicated that the methoxyl provides good activity with lower cytotoxicity to mammalian cells. The results from SAR analyses suggest different mechanisms of action between the neutral and basic compounds. In summary, the analogues represent important activity against these parasites and must be prototypes for further exploitation.

  DOI：

  10.1016/j.ejps.2018.06.023
• 作为产物：
  描述：

  辛胺 、 4-甲氧基苯甲醛 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-(4-methoxybenzylidene)octan-1-amine
  参考文献：
  名称：

  胡椒（Piper malacophyllum）及其类似物的新烯基衍生物：对克氏锥虫和婴儿利什曼原虫的抗寄生虫活性

  摘要：

  从Piper malacophyllum中分离出的链烯基苯分子显示出有希望的抗寄生虫活性和低细胞毒性。制备了几种合成类似物以优化对克鲁斯锥虫和婴儿利什曼原虫的活性。胺类似物是最有前途的。

  DOI：

  10.1111/cbdd.12986

文献信息

• Direct and mild palladium-catalyzed aerobic oxidative synthesis of imines from alcohols and amines under ambient conditions
  作者：Lan Jiang、Luolu Jin、Haiwen Tian、Xueqin Yuan、Xiaochun Yu、Qing Xu

  DOI：10.1039/c1cc14242a

  日期：——

  By ligand, TEMPO, and base screening, we developed a mild and green one-pot imine synthesis from alcohols and amines via a low-loading palladium-catalyzed tandem aerobic alcohol oxidation-dehydrative condensation reaction that can be readily carried out in open air at room temperature.

  通过配体，TEMPO和碱筛选，我们通过低负载钯催化的串联好氧醇氧化脱水缩合反应开发了一种由醇和胺合成的温和绿色一锅式亚胺合成方法，该反应可轻松地在露天进行。室内温度。
• Table salt as a catalyst for the oxidation of aromatic alcohols and amines to acids and imines in aqueous medium: effectively carrying out oxidation reactions in sea water
  作者：Susanta Hazra、Ajay Kishor Kushawaha、Deepak Yadav、Pritam Dolui、Mayukh Deb、Anil J. Elias

  DOI：10.1039/c9gc00497a

  日期：——

  carboxylic acids, ketones and imines. Oxidation of aromatic alcohols was carried out using NaCl (20 mol%) as the catalyst, NaOH (50 mol%) and aq. TBHP (4 equiv.) as the oxidant in 55–92% isolated yields. Oxidation of aromatic amines to imines was achieved by using only 20 mol% of NaCl and aq. TBHP (4 equiv.) in 32–93% isolated yields. The chlorine species formed during the reaction as the active oxidation

  已经基于氯化物开发了一种简单，有效，可持续和经济的氧化醇和胺的方法，氯化物是一种富含海的阴离子催化剂，用于实际合成各种羧酸，酮和亚胺。使用NaCl（20 mol％）作为催化剂，NaOH（50 mol％）和NaOH水溶液进行芳族醇的氧化。TBHP（4当量）作为氧化剂，分离产率为55-92％。通过仅使用20mol％的NaCl和NaCl水溶液将芳族胺氧化为亚胺。TBHP（4当量），分离产率为32–93％。该反应作为活性氧化催化剂中形成的氯物质已被确定为CLO 2 -醇类和C10 - / CLO 2 -通过对照实验获得胺。该方法几乎没有色谱纯化方法，因此适合大规模合成。我们已经将羧酸和亚胺的合成规模扩大到了30克，收率很高，并且还使用过滤后的海水作为溶剂和催化剂，有效地进行了这种新方法。
• New alkenyl derivative from <i>Piper malacophyllum</i> and analogues: Antiparasitic activity against <i>Trypanosoma cruzi</i> and <i>Leishmania infantum</i>
  作者：Marina T. Varela、Marta L. Lima、Mariana K. Galuppo、Andre G. Tempone、Alberto de Oliveira、João Henrique G. Lago、João Paulo S. Fernandes

  DOI：10.1111/cbdd.12986

  日期：2017.11

  Alkenylbenzene molecules isolated from Piper malacophyllum have shown promising antiparasitic activity and low cytotoxicity. Several synthetic analogues were prepared to optimize the activity against Trypanosoma cruzi and Leishmania infantum. The amine analogues were the most promising.

  从Piper malacophyllum中分离出的链烯基苯分子显示出有希望的抗寄生虫活性和低细胞毒性。制备了几种合成类似物以优化对克鲁斯锥虫和婴儿利什曼原虫的活性。胺类似物是最有前途的。
• Cycloadditionen von Heterocumulenen an C?N-Bindungssysteme. 3. Mitteilung. Bildung von Dihydro-1,3,5-oxadiazin- und Perhydro-s-triazinthionen bei der Reaktion von Iminodithiocarbonaten und Azomethinen mit Aroylisothiocyanaten
  作者：Karlheinz Milzner、Karl Seckinger

  DOI：10.1002/hlca.19740570615

  日期：——

  The iminodithiocarbonates 5a–5g and the N-(p-methoxybenzylidene)amines 6a–61 undergo 4 + 2-cycloaddition with the aroyl isothiocyanates 4a–4f to yield the expected dihydro-1,3,5-oxadiazine-4-thiones 7, 8 and 14.

  亚氨基二硫代碳酸酯5a-5g和N-（对甲氧基苄叉基）胺6a-61与芳基异硫氰酸酯4a-4f进行4 + 2-环加成反应，得到预期的二氢-1,3,5-恶二嗪-4-硫酮7， 8和14。
• Efficient and versatile synthesis of imines from alcohols and amines over CdS-SnS2 of heterostructure under visible-light irradiation
  作者：Xi-Ping Tan、Lang Chen、Sheng Shen、Jun-Kang Guo、Chak-Tong Au、Shuang-Feng Yin

  DOI：10.1016/j.apcata.2022.118660

  日期：2022.6

  Imines are important N-containing intermediates in organic synthesis. The photocatalytic production of specific imines through direct coupling of alcohols and amines under mild conditions has been widely explored. However, the reported processes are not practical due to negative factors such as low photocatalytic efficiency, involvement of non-stoichiometric raw materials, limited scope of substrates

  亚胺是有机合成中重要的含氮中间体。在温和条件下通过醇和胺的直接偶联光催化生产特定亚胺已被广泛探索。然而，由于光催化效率低、涉及非化学计量原料、基材范围有限以及需要不环保的添加剂等负面因素，所报道的工艺并不实用。在此，我们报道了通过一步水热法合成具有致密异质结的CdS-SnS 2光催化剂。以空气为氧化剂，无需添加剂，制备的CdS-SnS 2复合材料在可见光照射下从具有不同官能团的伯胺和醇生成亚胺表现出良好至优异的活性（胺的转化率高达 98%，对相应亚胺的选择性高达 99.9%）。与大多数报告的方法不同，本议定书涉及等量的酒精和胺。提出了一种基于活性物质猝灭的反应机理。目前的工作为在温和条件下通过醇和胺的交叉偶联合成亚胺提供了一种有效、通用和原子经济的方法。