4-methoxy-N-octylbenzamide | 145575-70-8

• 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-octylbenzamide
• 英文别名: N-octyl-4-methoxybenzamide；octyl 4-methoxybenzylamide；LINS03018
• CAS: 145575-70-8
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: PFPZBGVQHQRDIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-octylbenzamide 在 氯化亚砜 作用下， 反应 24.0h， 生成 C₁₆H₂₄ClNO
  参考文献：
  名称：

  Car催化将碳二亚胺插入芳族和杂芳族亚胺酸酯的CH键中，合成1,3-二氨基异二氢吲哚

  摘要：

  据报道，由C或杂芳族酰亚胺和碳二亚胺通过C键活化activation催化的1，3-二亚氨基异吲哚啉及其相关化合物的synthesis催化合成。该反应是过渡金属催化的碳二亚胺插入芳族或杂芳族CH键的第一个例子，也是合成1，3-二亚氨基二氢吲哚及其相关化合物的新方法。使用这种方法很容易获得不对称的1,3-二亚氨基异吲哚啉。使用多种底物，反应以良好至优异的产率进行。

  DOI：

  10.1021/acs.orglett.6b01012
• 作为产物：
  描述：

  4-甲氧基-2-苯基苯乙酮 在 sodium azide 、 碘 、 caesium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 4-methoxy-N-octylbenzamide
  参考文献：
  名称：

  2,2-二叠氮基-1,2-二芳基酮：与伯胺的合成及反应性

  摘要：

  描述了通过碘与叠氮化钠直接氧化叠氮化1,2-二叠氮基1,2-diarylethanones的合成方法。反应性研究表明，在碱性条件下用伯胺处理后，叠氮化物会分裂为酰胺和腈。

  DOI：

  10.1002/ejoc.201900292

文献信息

• Transamidation of amides with amines under solvent-free conditions using a CeO2 catalyst
  作者：Masazumi Tamura、Takuya Tonomura、Ken-ichi Shimizu、Atsushi Satsuma

  DOI：10.1039/c2gc16316k

  日期：——

  with n-octylamine. CeO2 acts as a reusable and effective heterogeneous catalyst for transamidation under solvent-free conditions. Transamidation of a variety of amides and amines produced the corresponding N-alkyl amides in high yields. This method provides the first example of a heterogeneous catalyst for transamidation using aliphatic amines as substrates. Characterization of acid–base properties

  各种金属之中 氧化物，氧化铈（CeO 2）表现出最高的氨基转移催化活性。吡啶甲酰胺 和 正辛胺。CeO 2充当可重用和有效的异构体催化剂 在下转氨 溶剂无条件。多种氨基转移酰胺类 和 胺类以高收率生产了相应的N-烷基酰胺。此方法提供了异构的第一个示例催化剂 用于使用脂肪族的转酰胺基 胺类作为底物。酸碱性质的表征和动力学研究表明，弱路易斯酸位点与相邻强碱位点的协同作用在氨基转移反应中起着重要作用。
• Highly Efficient Microwave-Assisted CO Aminocarbonylation with a Recyclable Pd(II)/TPP-β-Cyclodextrin Cross-Linked Catalyst
  作者：Emanuela Calcio Gaudino、Diego Carnaroglio、Katia Martina、Giovanni Palmisano、Andrea Penoni、Giancarlo Cravotto

  DOI：10.1021/op5003374

  日期：2015.4.17

  The incorporation of the carbonyl moiety into organic molecules using a three-component matrix, including carbon monoxide, an organic halide, and a nucleophilic component, offers a simple and versatile approach to the formation of carboxylic acids, anhydrides, esters, amides, and ketones. The design of a sustainable synthetic protocol for aminocarbonylation can be efficiently accomplished using a multifaceted

  使用三组分基质（包括一氧化碳，有机卤化物和亲核组分）将羰基部分掺入有机分子，为形成羧酸，酸酐，酯，酰胺和酮提供了一种简单而通用的方法。氨基羰基化的可持续合成方案的设计可以使用结合了固态绿色催化剂和合适的使能技术的多方面策略有效完成。在微波反应器中在压力下安全和协同使用一氧化碳可能会在氨基羰基化反应中产生技术突破。而且，
• Diamine-functionalized porous graphene oxide sheets decorated with palladium oxide nanoparticles for the oxidative amidation of aldehydes
  作者：Digvijay Sah、Surabhi、Padmini Gupta、Javaid Shabir、Manjeet Dhama、Subho Mozumdar

  DOI：10.1039/d2nj03807b

  日期：——

  In this work, a simple and stepwise strategy has been adopted for the successful synthesis of diamine functionalized porous graphene oxide sheets decorated with ultra-small palladium oxide nanoparticles. The successful synthesis, stepwise functionalization, morphology and elemental composition have been authenticated by using numerous physicochemical characterization techniques such as FT-IR, TGA,

  在这项工作中，采用简单而逐步的策略成功合成了装饰有超小氧化钯纳米粒子的二胺功能化多孔氧化石墨烯片。通过使用多种物理化学表征技术，如 FT-IR、TGA、粉末 XRD、SEM、HR-TEM、EDAX、元素映射、CHNS、ICP-MS 和 XPS 分析，对成功的合成、逐步功能化、形态和元素组成进行了验证. 制备的纳米催化剂已被用作可回收的催化剂，用于醛与胺的氧化酰胺化。这种纳米催化剂的主要特点包括反应条件温和、后处理程序简单、产品收率高、无任何有害副产物以及可循环使用多个催化循环。
• Fe3+-exchanged clay catalyzed transamidation of amides with amines under solvent-free condition
  作者：Md. Ayub Ali、S.M.A. Hakim Siddiki、Kenichi Kon、Ken-ichi Shimizu

  DOI：10.1016/j.tetlet.2013.12.111

  日期：2014.2

  Fe3+-exchanged montmorillonite is shown to be an effective and reusable heterogeneous catalyst for the transamidation of various amides and amines under solvent-free condition. The catalyst shows high yields and wide substrate scope. (C) 2014 Elsevier Ltd. All rights reserved.
• Antiparasitic activity of new gibbilimbol analogues and SAR analysis through efficiency and statistical methods
  作者：Marina T. Varela、Maiara M. Romaneli、Marta L. Lima、Samanta E.T. Borborema、Andre G. Tempone、João P.S. Fernandes

  DOI：10.1016/j.ejps.2018.06.023

  日期：2018.9

  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.