N-(2-furylmethyl)-N-(4-nitrobenzyl)amine | 81404-57-1

• 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: N-(2-furylmethyl)-N-(4-nitrobenzyl)amine
• 英文别名: N-4-nitrobenzyl furfurylamine；N-(furan-2-ylmethyl)-1-(4-nitrophenyl)methanamine
• CAS: 81404-57-1
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: VNUBGWPQRFDTPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-furylmethyl)-N-(4-nitrobenzyl)amine 在 sulphuryl azide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以45%的产率得到2-(((azidosulfonyl)(4-nitrobenzyl)amino)methyl)furan
  参考文献：
  名称：

  氨磺酰基叠氮化物的热重排：反应性和机理研究

  摘要：

  据报道，在热条件下，氨磺酰叠氮化物会重排形成一个C–C键，同时打破两个C–N键。机理研究表明，该反应经过库尔修斯式重排形成1，1-二氮杂苯，然后可能通过协同重排过程和逐步自由基过程进行重排。该重排可用于合成复杂的生物活性分子，例如固醇和胡椒碱衍生物。

  DOI：

  10.1021/acs.joc.7b00308
• 作为产物：
  描述：

  (4-nitrobenzylidene)(furan-2-yl)methylamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 N-(2-furylmethyl)-N-(4-nitrobenzyl)amine
  参考文献：
  名称：

  糠醛胺和柠康酸酐中的柠康酸的分子内Diels-Alder反应：呋喃环中取代基对区域选择性的影响

  摘要：

  由呋喃环中的取代基和反应条件可以控制N-苄基糠胺和柠康酸酐衍生的糠基柠檬烯二酸酯分子内Diels-Alder（IMDA）反应中的区域选择性。在动力学条件下进行的反应导致在1,3-关系中具有甲基和氨基亚甲基取代基的环加成产物，而在热力学条件下，除3-甲基硫烷基外，该产物重排成更稳定的环加合物，其中取代基位于1 ，2-关系。可以根据边界轨道相互作用和空间考虑因素来解释产物的形成。

  DOI：

  10.1016/s0040-4020(01)00175-2

文献信息

• Synthetic bioregulators of poly-cis carotenoid biosynthesis
  作者：Stephen M. Poling、Wan-Jean Hsu、Henry Yokoyama

  DOI：10.1016/0031-9422(82)83148-8

  日期：——

  to induce the biosynthesis of poly- cis carotenes in the flavedo of Marsh white seedless grapefruit. The effects of these new bioregulators are the same as that of the previously reported dibenzylamines, but several of the new compounds are more effective and cause the accumulation of up to 162 μg/g dry wt of poly- cis carotenes in the flavedo as compared to the maximum of 74 μg/g dry wt observed previously

  摘要 合成了 17 种新的生物调节剂，并测试了它们在沼泽白无籽葡萄柚果皮中诱导多顺式胡萝卜素生物合成的能力。这些新的生物调节剂的作用与之前报道的二苄胺的作用相同，但有几种新化合物更有效，与相比之下，在 flavedo 中积累了高达 162 μg/g 干重的多顺式胡萝卜素。先前观察到的最大值为 74 μg/g 干重。测试的化合物是取代的N-苄基糠胺、N-苄基、N-甲基糠胺和N-烷基、N-甲基苄胺。它们证明了叔胺和仲胺刺激多顺式胡萝卜素形成的能力。N-(4-溴苄基)糠胺的相互作用，一种更有效的新化合物，
• Unexpected rearrangement of intramolecular Diels-Alder adducts of citraconic anhydride and secondary furfuryl amines
  作者：Rajappa Murali、Hans W. Scheeren

  DOI：10.1016/s0040-4039(99)00316-0

  日期：1999.4

  The intramolecular Diels-Alder reactions of citraconic anhydride with several secondary furfuryl amines have been studied at different temperatures. At high temperatures, only a single cycloadduct was isolated, whilst at room temperature, a mixture of two regioisomeric adducts were formed. One of the regioisomers rearranged to another when heated in a solvent. Some aspects of the mechanism were investigated

  柠康酸酐与几种仲糠基胺的分子内Diels-Alder反应已在不同温度下进行了研究。在高温下，仅分离出一个环加合物，而在室温下，形成了两种区域异构加合物的混合物。当在溶剂中加热时，一种区域异构体重排为另一种。对该机制的某些方面进行了研究。
• Impact of substituents on the crystal structures and anti-leishmanial activity of new homoleptic Bi(<scp>iii</scp>) dithiocarbamates
  作者：Anamika Anamika、Rajan Singh、Krishna K. Manar、Chote Lal Yadav、Akhilesh Kumar、Rakesh K. Singh、Michael. G. B. Drew、Nanhai Singh

  DOI：10.1039/c9nj04477a

  日期：——

  homoleptic Bi(III) dithiocarbamate complexes, [Bi(L1-L6)3] ( L1 = (N-4-nitrobenzyl-N-furfuryl) dithiocarbamate 1, L2 = (N-4-chlorobenzyl-N-3-methylpyridyl)dithiocarbamate 2, L3 = (N-4-bromobenzyl-N-3-methylpyridyl)dithiocarbamate 3, L4 = (N-4-dimethylaminobenzyl-N-3-methylpyridyl) dithiocarbamate 4, L5 = (1-(2-pyridyl) piperazine) dithiocarbamate 5 and L6 = (N-4-methoxybenzyl-N-benzyl) dithiocarbamate 6) have

  六种新的功能化均化Bi（III）二硫代氨基甲酸酯配合物，[Bi（L1-L6）3]（L1 =（N-4-硝基苄基-N-糠基）二硫代氨基甲酸酯1，L2 =（N-4-氯苄基-N-3-甲基吡啶基）二硫代氨基甲酸酯2，L3 =（N-4-溴苄基-N-3-甲基吡啶基）二硫代氨基甲酸酯3，L4 =​​（N-4-二甲基氨基苄基-N-3-甲基吡啶基）二硫代氨基甲酸酯4，L5 =（1-（2-吡啶基）哌嗪）二硫代氨基甲酸酯5和L6 =（N-4-甲氧基苄基-N-苄基）二硫代氨基甲酸酯6）已制备并通过元素分析，粉末X射线衍射（PXRD）和（IR，UV–Vis，1H和13C 1H} NMR）光谱。六种配合物的结构已通过X射线晶体学以固态显示，并通过DFT计算进行了评估。配合物1和（2，5和6）是类似的二聚体，其中三个二硫代氨基甲酸酯配体分别以不对称的S，S-二齿和μ2，κ2S，S-螯合/螯合-桥接方式与七个和八个坐标的
• Influence of functionalities over polymer, trimer, dimer formation and optical properties of cadmium dithiocarbamates
  作者：Krishna K. Manar、Manoj K. Yadav、Anamika、Michael G.B. Drew、Nanhai Singh

  DOI：10.1016/j.poly.2016.06.047

  日期：2016.10

  Homoleptic cadmium(II) bis(dithiocarbamate) complexes having polymeric [Cd(L)(2)](infinity) (L = C(7)H(5)0(2)CH(2)NCS(2)CH(2)C(6)H(5) (L1), 1; C6H4NO2CH2NCS2CH2C4H3O (L2), 2; C6H4FCH2NCS2CH2C4H3O (L3), 3), trinuclear [Cd(L4)(2)](3) (L4 = 4-ClC6H4CH2NCS2CH2C4H3O, 4) and dinuclear [Cd(L5)(2)](2), (L5= 3-CIC6H4CH2NCS2CH2C6H5, 5) structures have been synthesized and characterized by elemental analyses, spectroscopy (IR, H-1 and C-13 H-1} NMR and UV-Vis.) and their structures have been revealed by X-ray crystallography. In 1-3 the dithiocarbamate ligands are uniquely bonded to the Cd atoms in a mu(2),kappa(2) S, S-chelating-bridging fashion, portraying 1D coordination polymeric structures in which the cadmium (II) ions adopt six coordinate distorted octahedral structures. In 4 the six dithiocarbamate ligands are spectacularly arranged about the Cd atoms resulting in a centrosymmetric trinuclear complex in which the central metal adopts an octahedral geometry and the terminal Cd atoms are in square pyramidal environments. Complex 5 has the well-established centrosymmetric dimeric structure in which the metal atoms have a five-coordinate trigonal bipyramidal geometry. Complexes 1-4 are rare examples of polymeric and trinuclear cadmium dithiocarbamate complexes. 1-5 show luminescent characteristics in solution and in the solid state arising from the metal perturbed intra-ligand charge transfer (ILCT) states. Their TG analyses show a single step decomposition with the formation of CdS nanoparticles, which have been examined by PXRD and HRTEM. (C) 2016 Elsevier Ltd. All rights reserved.
• Design, synthesis and structure–activity relationships of antiproliferative 1,3-disubstituted urea derivatives
  作者：Huan-Qiu Li、Tao-Tao Zhu、Tao Yan、Yin Luo、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2008.04.011

  日期：2009.2

  Twenty-four new 1,3-disubstituted urea derivatives (compounds 1-24) were synthesized and reported for the first time. The antiproliferative activities of these compounds were evaluated against a panel of one human liver cell line (L02) and two human tumor cell lines (KB and K562) by applying the MTT colorimetric assay. The series of 1,3-disubstituted urea derivatives show good antiproliferative activity against human cancer cell lines (KB and K562) and no antiproliferative activity against liver cell line (L02). The potent in vitro antiproliferative activity of these derivatives and their selectivity for L02 are quite important points for an anticancer drug candidate with fewer side effects. Structure-activity relationships were also discussed based on the obtained experimental data. The hydroxyl groups on the phenyl ring reduced the antiproliferative activities of 1,3-disubstituted urea derivatives. The OH groups could be responsible for a reduction in the permeability of the cell membrane. Generally, an aromatic ring on N-3 seems to be in favor of enhancing the inhibitory activity, compounds introduced a nitro group substituent at C-3 position on the aromatic ring approved to generally decrease activity. (C) 2008 Elsevier Masson SAS. All rights reserved.