N-(4-fluorobenzyl)-N'-methylethane-1,2-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'-methylethane-1,2-diamine
• 英文别名: N'-[(4-fluorophenyl)methyl]-N-methylethane-1,2-diamine
• 化学式: C₁₀H₁₅FN₂
• 分子量: 182.241
• InChiKey: FWVQLQQIOINENG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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'-methylethane-1,2-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78%的产率得到7,7,9,9-Tetrachloro-4-[(4-fluorophenyl)methyl]-1-methyl-1,4,6,8,10-pentaza-5lambda5,7lambda5,9lambda5-triphosphaspiro[4.5]deca-5(10),6,8-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86%的产率得到N-(4-fluorobenzyl)-N'-methylethane-1,2-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

• 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
• 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
• Phosphorus–nitrogen compounds. Part 37. Syntheses and structural characterizations, biological activities of mono and bis(4-fluorobenzyl)spirocyclotetraphosphazenes
  作者：Gamze Elmas、Aytuğ Okumuş、Pelin Sevinç、Zeynel Kılıç、Leyla Açık、Mustafa Atalan、Mustafa Türk、Gökberk Deniz、Tuncer Hökelek

  DOI：10.1039/c7nj00478h

  日期：——

  established by X-ray crystallography. The antibacterial activities of the compounds against G(+) and G(−) bacteria and their antifungal activities against yeast strains were scrutinized. The results indicated that 4a and 5a were the most active compounds, especially to yeast strains. In addition, it was found that the most active compound toward DNA was 8. The cytotoxic activities of the cyclotetraphosphazenes

  八氯环四磷腈N 4 P 4 Cl 8与一等摩尔量的（4-氟苄基）二胺（1-3）的Cl取代反应提供了单（4-氟苄基）螺环四磷腈（4-6）作为次要产物。但是，N 4 P 4 Cl 8与两个等摩尔量的（4-氟苄基）二胺（1-3）的反应导致形成单（4-6），2-反式-6-双（7-9）作为主要产品）和2-顺-6-双（4-氟苄基）螺环四磷腈（10-12）。2-顺式使用柱色谱法分离和纯化-6-bis化合物（10和12），为次要产物，而无法分离出化合物11。使单-螺（4-6）和2-反--6-双-螺（7-9）环四磷腈与过量的吡咯烷在THF中反应，得到完全取代的六吡咯烷酮（4a-6a）和四吡咯烷酮（7a-9a）产品产量高。化合物9也与哌啶，吗啉和1,4-二氧杂-8-氮杂螺[4,5]癸烷（DASD）反应，得到四氨基产物（9b，9c和9d），由于其非常高的产量。环四磷腈的元素分析，质谱（ESI-MS），傅立叶变换红外（FTIR）光谱和1