N'-(1-ferrocenylmethyl)-N-ethylethylenediamine | 1253964-12-3

• 英文名称: N'-(1-ferrocenylmethyl)-N-ethylethylenediamine
• 英文别名: N-(1-ferrocenylmethyl)-N-ethlyethylenediamine；N-(ferrocenylmethyl)-N-ethylethylenediamine
• CAS: 1253964-12-3
• 化学式: C₁₅H₂₂FeN₂
• 分子量: 286.2
• InChiKey: BMFHYLISGHOMGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  六氯环三磷腈 、 N'-(1-ferrocenylmethyl)-N-ethylethylenediamine 在 N(C₂H₅)3 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到spiro(ethane-1,2-diamino)[N-(ferrocenylmethyl)-N-ethyl]-4,4,6,6-tetrachlorocyclotriphosphazatriene
  参考文献：
  名称：

  Phosphorus–nitrogen compounds: Part 19. Syntheses, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic monoferrocenylcyclotriphosphazenes

  摘要：

  The reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N-alkyl-N-ferrocenylmethylethylene diamines, FcCH(2)NH(CH2)(2)NHR1 [R-1 = Me (1) and Et (2)], and sodium [3-(N-ferrocenylmethylamino)-1-propanoxide] (3) produce spirocyclic monoferrocenyl tetrachlorophosphazenes (1a-3a). The tetrapyrroli-dinophosphazenes (1b-3b) are prepared from the reactions of corresponding phosphazenes (1a-3a) with excess pyrrolidine. The reaction of 1a with excess morpholine affords geminal-morpholino phosphazene (1c), whilst the reactions of 2a and 3a give diethylaminotrimorpholino (2c) and fully substituted morpholino products (3c), respectively. The structural investigations of the compounds are examined by Fourier transform IR, MS, H-1, C-13, P-31 NMR, DEPT, HETCOR, and HMBC techniques. The crystal structures of 3b and 3c are determined using X-ray crystallography. Cyclic voltammetric and chronoamperometric data show that compounds 1a-3a, 1b-3b, and 1c-3c exhibit electrochemically reversible one-electron oxidation of Fc redox centers which are hardly affected by the substituents on the phosphazene ring. The compounds 1b, 2b, 3b, and 3c are screened for antibacterial activities against Gram-positive and Gram-negative bacteria and for antifungal activities against yeast strains. In addition, the antituberculosis activities (in vitro) of these compounds are evaluated against INH-susceptible reference strain M. tuberculosis H37Rv, and six multi-drug resistant clinical M. tuberculosis isolates. Compound 2b is found to be the most active against the susceptible the reference strain. In addition, 1b, 2b, and 3c are active against all the multidrug-resistant clinical isolates at the highest concentrations. Gel electrophoresis data indicate that the compounds promote the formation of strand breaks in plasmid DNA. Almost all the concentrations lost of supercoiled DNA suggests that the compound 3b is very efficient plasmid-modifier. The compounds inhibit BamHI cleavage of pUC18 DNA while restricting HindIII. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.07.017
• 作为产物：
  描述：

  N-乙基乙二胺 、 二茂铁甲醛 、 sodium tetrahydroborate 以 甲醇 为溶剂， 以93%的产率得到N'-(1-ferrocenylmethyl)-N-ethylethylenediamine
  参考文献：
  名称：

  Phosphorus–nitrogen compounds: Part 19. Syntheses, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic monoferrocenylcyclotriphosphazenes

  摘要：

  The reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N-alkyl-N-ferrocenylmethylethylene diamines, FcCH(2)NH(CH2)(2)NHR1 [R-1 = Me (1) and Et (2)], and sodium [3-(N-ferrocenylmethylamino)-1-propanoxide] (3) produce spirocyclic monoferrocenyl tetrachlorophosphazenes (1a-3a). The tetrapyrroli-dinophosphazenes (1b-3b) are prepared from the reactions of corresponding phosphazenes (1a-3a) with excess pyrrolidine. The reaction of 1a with excess morpholine affords geminal-morpholino phosphazene (1c), whilst the reactions of 2a and 3a give diethylaminotrimorpholino (2c) and fully substituted morpholino products (3c), respectively. The structural investigations of the compounds are examined by Fourier transform IR, MS, H-1, C-13, P-31 NMR, DEPT, HETCOR, and HMBC techniques. The crystal structures of 3b and 3c are determined using X-ray crystallography. Cyclic voltammetric and chronoamperometric data show that compounds 1a-3a, 1b-3b, and 1c-3c exhibit electrochemically reversible one-electron oxidation of Fc redox centers which are hardly affected by the substituents on the phosphazene ring. The compounds 1b, 2b, 3b, and 3c are screened for antibacterial activities against Gram-positive and Gram-negative bacteria and for antifungal activities against yeast strains. In addition, the antituberculosis activities (in vitro) of these compounds are evaluated against INH-susceptible reference strain M. tuberculosis H37Rv, and six multi-drug resistant clinical M. tuberculosis isolates. Compound 2b is found to be the most active against the susceptible the reference strain. In addition, 1b, 2b, and 3c are active against all the multidrug-resistant clinical isolates at the highest concentrations. Gel electrophoresis data indicate that the compounds promote the formation of strand breaks in plasmid DNA. Almost all the concentrations lost of supercoiled DNA suggests that the compound 3b is very efficient plasmid-modifier. The compounds inhibit BamHI cleavage of pUC18 DNA while restricting HindIII. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.07.017

文献信息

• Phosphorus–nitrogen compounds. Part 29. Syntheses, crystal structures, spectroscopic and stereogenic properties, electrochemical investigations, antituberculosis, antimicrobial and cytotoxic activities and DNA interactions of ansa-spiro-ansa cyclotetraphosphazenes
  作者：Gamze Elmas、Aytuğ Okumuş、L.Yasemin Koç、Hossien Soltanzade、Zeynel Kılıç、Tuncer Hökelek、Hakan Dal、Leyla Açık、Zafer Üstündağ、Devrim Dündar、Makbule Yavuz

  DOI：10.1016/j.ejmech.2014.10.005

  日期：2014.11

  A number of novel ansa-spiro-ansa (asa) cyclotetraphosphazenes (1a–5b) was prepared in the range of 63–90 % yields. The structures of the compounds were verified by MS, FTIR, 1H, 13C1H} and 31P1H} NMR, heteronuclear single quantum coherence (HSQC), and heteronuclear multiple-bond correlation (HMBC) techniques. The crystal structures of 1b, 2c and 5a were determined by X-ray crystallography. The compound

  制备了许多新颖的ansa-spiro-ansa（asa）环四磷腈（1a - 5b），产率为63-90％。通过MS，FTIR，1 H，13 C 1 H}和31 P 1 H} NMR，异核单量子相干（HSQC）和异核多键相关（HMBC）技术验证了化合物的结构。通过X射线晶体学确定1b，2c和5a的晶体结构。化合物2c中通过在改变分析31 p 1除了手性溶剂之外，还具有1 H NMR谱。（R）-（+）-2,2,2-三氟-1-（9'-蒽基）-乙醇（CSA），以研究其立体感。结果支持发现化合物2c存在于外消旋混合物中。单二茂铁基-螺-芳基-环四磷腈的循环伏安和计时安培数据显示了Fe氧化还原中心的电化学可逆单电子氧化。评价了单二茂铁基-螺旋-asa化合物（3a – 5b）对参考菌株结核分枝杆菌H37Rv和结核分枝杆菌的抗结核活性。对利福平和异烟肼有抗药性的临床菌株。这些化合物似乎不是用作临
• Phosphorus–nitrogen compounds. Part 35. Syntheses, spectroscopic and electrochemical properties, and antituberculosis, antimicrobial and cytotoxic activities of mono-ferrocenyl-spirocyclotetraphosphazenes
  作者：Aytuğ Okumuş、Gamze Elmas、Reşit Cemaloğlu、Betül Aydın、Arzu Binici、Hülya Şimşek、Leyla Açık、Mustafa Türk、Remziye Güzel、Zeynel Kılıç、Tuncer Hökelek

  DOI：10.1039/c6nj00204h

  日期：——

  The syntheses, in vitro antituberculosis and cytotoxic activities of cyclotetraphosphazenes were investigated.

  翻译结果：研究了环四磷氮杂烷的合成、体外抗结核和细胞毒性活性。
• Syntheses, spectroscopic and crystallographic characterizations of<i>cis</i>- and<i>trans</i>-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activities
  作者：Yasemin Tümer、Nuran Asmafiliz、C. Tuğrul Zeyrek、Zeynel Kılıç、Leyla Açık、S. Pınar Çelik、Mustafa Türk、B. Çağdaş Tunalı、Hüseyin Ünver、Tuncer Hökelek

  DOI：10.1039/c7nj03643d

  日期：——

  performed using MS, FTIR, 1H, 13C and 31P NMR techniques. The crystal structures of 5 (with 8), 6, 7 and 9 were determined by X-ray crystallography. The most important result of this study was that the trans chiral phosphazenes crystallized as only one enantiomer. Studies of the antibacterial and antifungal activity of the phosphazenes (4–9) showed that compounds 6 and 7 were effective against P. vulgaris

  通过六氯环三磷腈（N 3 P 3 Cl 6）与分子式为FcCH 2 NH（CH 2）的N-烷基-N-单二茂铁基二胺的反应，获得了新的顺式（4-6）和反式-二螺环二茂铁基磷腈衍生物（7-9）。）n NHR [ n = 2，R = CH 3（1）; n = 2，R = C 2 H 5（2）和n = 3，R = CH 3（3）]。使用MS，FTIR，1 H，13 C和31 P NMR技术对产物进行表征。的晶体结构5（含8），6，7和9是由X-射线晶体学测定。该研究的最重要结果是反式手性磷腈结晶为仅一种对映体。对磷腈类化合物的抗菌和抗真菌活性的研究（4-9）表明，化合物6和7对寻常型肺炎克雷伯氏菌和肺炎克雷伯氏菌是有效的。。研究了4-9对L929成纤维细胞和DLD-1结肠癌细胞的细胞毒活性。DLD-1细胞系中4和7的坏死作用大于L929细胞系。DFT计算进行了使用B3LYP与LANL2DZ基组功能
• Phosphorus–nitrogen compounds: part 71. Novel unsymmetrically-substituted dispiro-cyclotriphosphazenes: synthesis, characterization, antituberculosis activity, and phototunable charge storage studies
  作者：Reşit Cemaloğlu、İpek Berberoğlu、Mehtap Yakut、Arzu Binici、Nuran Asmafiliz、Zeynel Kılıç、Remziye Güzel、Gülbahar Erdal、Hülya Şimşek、Tuncer Hökelek

  DOI：10.1039/d3nj04099b

  日期：——

  tetrachloromonospirophosphazenes as starting materials. Several spectroscopic techniques (mass spectrometry, FTIR, and 1H, 13C, and 31P NMR), as well as elemental analysis, were employed to characterize the new phosphazenes. All unsymmetrically substituted phosphazenes are expected to be racemic mixtures (RR′/SS′ and RS′/SR′) due to two different stereogenic P-centers. In addition, the molecular and crystal

  本研究的目的是合成和表征新型有机-无机杂化多杂环二氯二螺( N / N )环三磷腈并阐明其抗结核活性。为了实现这一目标，首先以二茂铁基二胺（4和5）和带有苄基的四氯单螺磷腈为起始原料，得到反式（6a-11a）和顺式（6b-11b）不对称二氯二螺（N / N ）环三磷腈。采用多种光谱技术（质谱、FTIR、1 H、13 C 和31 P NMR）以及元素分析来表征新型磷腈。由于两个不同的立构P中心，所有不对称取代的磷腈预计都是外消旋混合物（RR '/ SS '和RS '/ SR '）。此外，还通过单晶X射线晶体学阐明了cis - 6b、cis - 10b和cis - 11b异构体的分子和晶体结构。它们分别属于中心对称的C 2/ c、P 2 1 / c和P空间群；因此，它们的晶格必须包含两种对映体：RR '/ SS '或SR '/ RS '。此外，在可逆循环伏安图中仅观察到二茂铁基二螺磷腈的一个氧化还原波。磷腈的
• Phosphorus-nitrogen compounds. Part 72. Bisspiro(N/N)cyclotri-phosphazenes with 4-chlorobenzyl and ferrocenyl pendant arms: Synthesis, structural characterization, dye-sensitized solar cell fabrication and antituberculosis activity studies
  作者：İpek Berberoğlu、Reşit Cemaloğlu、Arzu Binici、Mehtap Yakut、Nuran Asmafiliz、Zeynel Kılıç、Remziye Güzel、Hülya Şimşek、Tuncer Hökelek

  DOI：10.1016/j.molstruc.2024.138305

  日期：2024.8

  FTIR and 31P NMR spectroscopies. Two different stereogenic P-centers are present in the unsymmetrically substituted inorganic-organic fused hybrid rings. These compounds may be in the form of racemic mixtures (RR'/SS' and RS'/SR'). The molecular and crystal structures of trans (6a and 7a) and cis (6b and 7b) isomers were elucidated by single-crystal X-ray structural crystallography. The space groups

  在本研究中，制备了具有 4-氯苄基和二茂铁基侧臂的二氯双螺（N/N）环三磷腈，以研究其光谱和晶体学特征以及抗结核活性。四氯(4-氯苄基)螺(N/N)环三磷腈与二茂铁基二胺(4和5)的氯取代反应产生含有不对称二氨基螺环的二氯双螺(N/N)环三磷腈。所有环三磷腈均通过质谱、FTIR 和 31P NMR 光谱进行表征。两个不同的立体异构P中心存在于不对称取代的无机-有机稠合杂环中。这些化合物可以是外消旋混合物的形式（RR'/SS'和RS'/SR'）。通过单晶X射线结构晶体学阐明了反式（6a和7a）和顺式（6b和7b）异构体的分子和晶体结构。 trans-6a、cis-6b、trans-7a和cis-7b的空间群分别是中心对称的P -1 、P bca 、P 21/n 和P bca 。因此，晶格包含两种对映体。 6a、6b、7a和7b的P2原子的绝对构型分别是R、R、S和S。确定磷腈6a、6b和10b中对结核分枝杆菌H37Rv(ATCC