N-(4-fluorobenzyl)-N'-methylpropane-1,3-diamine

• 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-(4-fluorobenzyl)-N'-methylpropane-1,3-diamine
• 英文别名: N'-[(4-fluorophenyl)methyl]-N-methylpropane-1,3-diamine
• 化学式: C₁₁H₁₇FN₂
• mdl: MFCD07408159
• 分子量: 196.268
• InChiKey: QDKQHTDTAQQNBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-fluorobenzyl)-N'-methylpropane-1,3-diamine 在 六氯环三磷腈 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以81%的产率得到2,2,4,4-Tetrachloro-11-[(4-fluorophenyl)methyl]-7-methyl-1,3,5,7,11-pentaza-2lambda5,4lambda5,6lambda5-triphosphaspiro[5.5]undeca-1(6),2,4-triene
  参考文献：
  名称：

  Phosphorus–nitrogen compounds part 27. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups

  摘要：

  A number of partly (7-9) and fully (10a-12d. Scheme 1) substituted mono(4-fluorobenzyl)spiro cyclotriphosphazenes was prepared. The structures of the compounds were determined by MS, FTIR, 1D and 2D NMR techniques. The crystal structures of 9, llb and 12b were verified by X-ray diffraction analysis. In vitro cytotoxic activity of the phosphazenes (10a-12d) against HeLa cervical cancer cell lines was evaluated. Compound 12c was found to be the most effective, as it is a cytotoxic reagent that might activate apoptosis by altering mitochondrial membrane potential. Compounds 10b, lib and 12b showed very good activity against yeast strains Candida tropicalis and Candida albicans. BamHI and HindIII digestion results demonstrate that the compounds (10a-12a, 10b-12b, 10d-12d), and (9,10c-12c) bind with GIG and A/A nucleotides, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.046
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到N-(4-fluorobenzyl)-N'-methylpropane-1,3-diamine
  参考文献：
  名称：

  Phosphorus–nitrogen compounds part 27. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups

  摘要：

  A number of partly (7-9) and fully (10a-12d. Scheme 1) substituted mono(4-fluorobenzyl)spiro cyclotriphosphazenes was prepared. The structures of the compounds were determined by MS, FTIR, 1D and 2D NMR techniques. The crystal structures of 9, llb and 12b were verified by X-ray diffraction analysis. In vitro cytotoxic activity of the phosphazenes (10a-12d) against HeLa cervical cancer cell lines was evaluated. Compound 12c was found to be the most effective, as it is a cytotoxic reagent that might activate apoptosis by altering mitochondrial membrane potential. Compounds 10b, lib and 12b showed very good activity against yeast strains Candida tropicalis and Candida albicans. BamHI and HindIII digestion results demonstrate that the compounds (10a-12a, 10b-12b, 10d-12d), and (9,10c-12c) bind with GIG and A/A nucleotides, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.046

文献信息

• The reactions of 2-<i>trans</i>-6-bis(4-fluorobenzyl)spirocyclotetraphosphazene with primary amines: spectroscopic and crystallographic characterizations
  作者：Gamze Elmas

  DOI：10.1080/10426507.2017.1359595

  日期：2017.11.2

  GRAPHICAL ABSTRACT ABSTRACT The substitution reactions of 2-trans-6-bis(4-fluorobenzyl)spirocyclotetraphosphazene (3; with a yield of 59%) are carried out with excess alkylamines, benzylamine, n-hexylamine, n-butylamine, n-propylamine and iso-propylamine in THF. As a result of these reactions, the fully substituted tetrabenzylamino (3a), tetrahexylamino (3b), tetrabutylamino (3c), tetrapropylamino

  图形摘要摘要 2-trans-6-bis(4-fluorobenzyl)spirocyclotetraphosphazene (3; 产率 59%) 与过量的烷基胺、苄胺、正己胺、正丁胺、正丙胺进行取代反应和异丙胺的 THF 溶液。作为这些反应的结果，完全取代的四苄基氨基 (3a)、四己基氨基 (3b)、四丁基氨基 (3c)、四丙基氨基 (3d) 和四异丙基氨基 (3e) 2-反-6-双-(4-氟苄基) 螺环四磷腈是以高产率获得。分离出的化合物 (3a-3e) 的结构特征通过元素分析、质谱 (ESI-MS)、傅里叶变换红外 (FTIR)、异核单量子相干 (HSQC)、异核多键相关 (HMBC) 和1H、13C1H}、31P1H} 核磁共振技术。3a 的固态和分子结构是使用 X 射线晶体学确定的。其晶胞中存在两个独立的分子。
• Phosphorus-Nitrogen compounds part 47: The conventional and microwave-assisted syntheses of dispirocyclotriphosphazene derivatives with (4-fluoro/4-nitrobenzyl) pendant arms: Structural and stereogenic properties and DNA interactions
  作者：Güler İnci Tanrıkulu、Mehtap Yakut Özgür、Aytuğ Okumuş、Zeynel Kılıç、Tuncer Hökelek、Betül Aydın、Leyla Açık

  DOI：10.1016/j.ica.2019.03.018

  日期：2019.5

  iphosphazene (1b) reacted with excess pyrrolidine to give fully substituted (1c) phosphazene. The structures of the new compounds were elucidated by elemental analyses, ESI-MS, FTIR, 1H, 13C, and 31P NMR techniques. The molecular and crystal structures of 1a, 3b and 6 were identified by single crystal X-ray crystallography. The absolute configurations of 3b and 6 were unambiguously established as SS

  摘要六氯环三磷腈N3P3Cl6与两个等摩尔量的N-烷基-N'-单（4-氟苄基）二胺（1-3），FC6H4 NH（CH2）nNHR1（n = 2和3，R1 = CH3）的Cl交换反应或C2H5）和N-烷基-N'-单（4-硝基苄基）二胺（4和5），NO2C6H4 NH（ ）nNHR1（n = 2，R1 = 或 ）导致单（ （4-氟苄基）（1a-3a）和单（4-硝基苄基）（4a和5a）螺环三磷腈为次要产物，以及反-双（4-氟苄基）（1b-3b）和反-双（4-硝基苄基）（ 4b和5b）螺环三磷腈为主要产物。双（4-氟苄基）螺环三磷腈（1b）与过量的吡咯烷反应，得到完全取代的（1c）磷腈。通过元素分析，ESI-MS，FTIR，1H，13C和31P NMR技术阐明了新化合物的结构。通过单晶X射线晶体学鉴定1a，3b和6的分子和晶体结构。使用X射线晶体学数据，将3b和6的绝对构型
• The comparative reactions of 2‐ <i>cis</i> ‐4‐ansa and spiro cyclotetraphosphazenes with difunctional ligands: Structural and stereogenic properties, electrochemical, antimicrobial and cytotoxic activity studies
  作者：Aytuğ Okumuş、Gamze Elmas、Zeynel Kılıç、Arzu Binici、Nagehan Ramazanoğlu、Leyla Açık、Bünyemin Çoşut、Tuncer Hökelek、Remziye Güzel、Beste Çağdaş Tunalı、Mustafa Türk、Hülya Şimşek

  DOI：10.1002/aoc.6150

  日期：2021.4

  one‐electron oxidation of Fe‐redox centre. As an example, the chirality of 3c was investigated by 31P NMR spectroscopy on the addition of (R)‐(+)‐2,2,2‐trifluoro‐1‐(9′‐anthryl)‐ethanol, chiral solvating agent (CSA). The circular dichroism (CD) (for 3d and 3e), HPLC (for 3d, 3e and 3f) and X‐ray (for 3f) display that these compounds have chirality (RS′ or SR′) in the solution and solid state. This paper

  在这项研究中，获得了两种化合物，分别是单二茂铁基-2-顺式-4-二氯安ans（2,4-安沙; 3）和单二茂铁-螺-螺（螺; 4）六氯环四磷腈。 N 4 P 4 Cl 8（1）与等摩尔量的3-（N-二茂铁基甲基氨基）-1-丙醇钠（2）的Cl置换反应。2,4-ansa（3）与过量的二胺和二烷氧化物的反应导致ansa-cyclotetraphosphazenes（3a-3e）的形成。斯皮罗（4）与过量的二胺和二氧化烯反应生成单二茂铁基-螺环-环四磷腈（4a–4d）。尽管2,4-柄（3）中产生的二螺（3A）与ñ - （4-氟苄基） - ñ '-methylethane -1,2-二胺，它提供两个单螺（图3b）和二螺（图3c）与ñ - （4-氟苄基）-N'-甲基丙烷-1,3-二胺。然而，螺（4）产生一个trispiro（4A）与ñ - （4-氟苄基） - ñ '-methylethane -1,2-二胺和2
• Synthesis of Bis(2,2,3,3-tetrafluoro-1,4-butanedialkoxy)-2-trans-6-bis(4-fluorobenzyl)spirocyclotetraphosphazene: Structural Characterization, Biological Activity and DFT Studies
  作者：Gamze Elmas、Zeynel Kılıç、Bünyemin Çoşut、Gürkan Keşan、Leyla Açık、Merve Çam、Beste Çağdaş Tunalı、Mustafa Türk、Tuncer Hökelek

  DOI：10.1007/s10870-020-00851-4

  日期：2021.6

  The Cl replacement reaction of octachlorocyclotetraphosphazene, N4P4Cl8 (1), with two equimolar amounts of N-(4-fluorobenzyl)-N′-methylpropane-1,3-diamine led to the formation of 4,4,8,8-tetrachloro-2-trans-6-bis-N-(4-fluorobenzyl)-N′-methylpropane-1,3-diamino-cyclotetraphosphazene (2). The reaction of 2 with excess sodium 2,2,3,3-tetrafluoro-1,4-butanedioxide afforded the bis(2,2,3,3-tetrafluoro-1,4-butanedialkoxy)-2-trans-6-bis(4-fluorobenzyl)spirocyclotetraphosphazene (2a). The elemental analyses, mass spectrum (ESI–MS), FTIR, HSQC, HMBC, 1H, 13C and 31P NMR spectral data of 2a were consistent with the proposed structure. The crystal structure of 2a was elucidated by X-ray diffraction method. The spectroscopic data of the molecules (2 and 2a) in the ground state were investigated by the Density Functional Theory (DFT) from the crystal structures. On the other hand, compound 2a was found to be the most active against S. aureus G(+) (MIC value: 125 µM). Whilst, any antifungal activity of 2a was not observed against C. albicans and C. tropicalis. This compound also exhibits cytotoxic activity against L929 fibroblast and MCF-7 breast cancer cells. The interaction of 2a with pBR322 DNA was researched using gel electrophoresis. It is understood that the change in DNA conformation by interstrand of 2a with A/A and G/G nucleobases in DNA. The synthesis, spectroscopic and crystallographic characterizations, biological activities and DFT studies of bis(2,2,3,3-tetrafluoro-1,4-butanedialkoxy)-2-trans-6-bis(4-fluorobenzyl)spirocyclotetraphosphazene were presented.

  八氯环磷氮烷 N4P4Cl8 (1) 与两个等摩尔量的 N-(4-氟苄基)-N′-甲基丙烷-1,3-二胺发生 Cl 置换反应，生成 4,4,8,8-四氯-2-反式-6-双-N-(4-氟苄基)-N′-甲基丙烷-1,3-二胺环磷氮烷 (2)。将 2 与过量的 2,2,3,3-四氟-1,4-丁二氧化钠反应，得到了双(2,2,3,3-四氟-1,4-丁二酰氧基)-2-反式-6-双(4-氟苄基)螺环四磷杂环(2a)。2a 的元素分析、质谱（ESI-MS）、傅立叶变换红外光谱（FTIR）、HSQC、HMBC、1H、13C 和 31P NMR 光谱数据均与所提出的结构相符。X 射线衍射法阐明了 2a 的晶体结构。根据晶体结构，利用密度泛函理论（DFT）研究了分子（2 和 2a）在基态时的光谱数据。另一方面，发现化合物 2a 对金黄色葡萄球菌 G（+）的活性最强（MIC 值：125 µM）。同时，没有观察到 2a 对白僵菌和热带僵菌有任何抗真菌活性。该化合物还对 L929 成纤维细胞和 MCF-7 乳腺癌细胞具有细胞毒性。凝胶电泳法研究了 2a 与 pBR322 DNA 的相互作用。据了解，2a 与 DNA 中的 A/A 和 G/G 核碱基的链间作用改变了 DNA 的构象。介绍了双(2,2,3,3-四氟-1,4-丁二酰氧基)-2-反式-6-双(4-氟苄基)螺环四磷嗪的合成、光谱和晶体学表征、生物活性和 DFT 研究。
• Phosphorus-nitrogen compounds. Part 44. The syntheses of N,N-spiro bridged cyclotriphosphazene derivatives with (4-fluorobenzyl) pendant arms: Structural and stereogenic properties, DNA interactions, antimicrobial and cytotoxic activities
  作者：Ezel Öztürk、Aytuğ Okumuş、Zeynel Kılıç、Adem Kılıç、Hande Kayalak、Leyla Açık、Nebahat Aytuna Çerçi、Mustafa Türk、Tuncer Hökelek

  DOI：10.1016/j.ica.2018.10.028

  日期：2019.2

  (2d, 2e, 2h and 2i). The structures of 2a and 2f are determined by X-ray crystallography. The stereogenic properties of 2a and 2f having four potential stereogenic P–centers are investigated by crystallography. The monospiro (2b–2e) and dispiro (2f–2i) products have one and two equivalent chiral centers, respectively. The dispiro derivatives may have two meso (trans-trans and cis-cis) and two racemate

  通过晶体学研究了具有四个潜在的立体P中心的2a和2f的立体学性质。单螺（2b–2e）和双螺（2f–2i）产品分别具有一个和两个等效的手性中心。该双螺衍生物可具有两种内消旋体（反式和反式和顺式-顺式）和两种外消旋物（反式-顺式和顺式-反式）的混合物。然而，发现2f的结构为反式-反式（内消旋）异构体。此外，还评估了2d和2h的体外抗菌和细胞毒性活性。该化合物对大肠杆菌和蜡状芽孢杆菌具有显着的生长抑制作用。化合物2d具有高度的抗癌和凋亡活性。该双螺衍生物可具有两种内消旋体（反式和反式和顺式-顺式）和两种外消旋物（反式-顺式和顺式-反式）的混合物。然而，发现2f的结构为反式-反式（内消旋）异构体。此外，还评估了2d和2h的体外抗菌和细胞毒性活性。该化合物对大肠杆菌和蜡状芽孢杆菌具有显着的生长抑制作用。化合物2d具有高度的抗癌和凋亡活性。该双螺衍生物可具有两种内消旋体（反式和反式和顺式-顺式）和两种