N,N'-Bis(4-fluorobenzyl)propane-1,3-diamine | 1242902-13-1

• 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,N'-Bis(4-fluorobenzyl)propane-1,3-diamine
• 英文别名: N,N'-bis[(4-fluorophenyl)methyl]propane-1,3-diamine
• CAS: 1242902-13-1
• 化学式: C₁₇H₂₀F₂N₂
• mdl: MFCD15732421
• 分子量: 290.356
• InChiKey: YIZHYPMWWQDQDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-Bis(4-fluorobenzyl)propane-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 58.0h， 生成 7,11-bis(4-fluorobenzyl)-2-chloro-2,4,4-trimorpholin-4-yl-1,3,5,7,11-pentaaza-2λ5,4λ5,6λ5-triphosphaspiro[5.5]undeca-1,3,5-triene
  参考文献：
  名称：

  Phosphorus–nitrogen compounds part 22. Syntheses, structural investigations, biological activities and DNA interactions of new mono and bis (4-fluorobenzyl) spirocyclophosphazenes

  摘要：

  The reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with mono (1 and 2) and bis(4-fluorobenzyl) diamines (3-5), FPhCH2NH(CH2)(n)NHR (R=H or FPhCH2-), produce mono (1a and 2a) and bis(4-fluorobenzyl) monospirocyclophosphazenes (3a-5a). The tetraaminomonospirocyclophosphazenes (1b-2d) are obtained from the reactions of the partly substituted phosphazenes (1a and 2a) with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The tetrachlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4a and 5a) with excess pyrrolidine, morpholine and DASD afford the fully substituted bis(4-fluorobenzyl) monospirocyclophosphazenes (4b, 4d-5d) in boiling THF. In addition, monochlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4e and 41) have also been isolated from the reactions with excess morpholine and DASD in boiling THF. The structural investigations of the compounds have been verified by elemental analyses, MS. FTIR, H-1, C-13, F-19 (for 1d and 2d). P-31 NMR, HSQC and HMBC techniques. The crystal structures of 3a, 4a, 5a and 2b have been determined by X-ray crystallography. The compounds 2a-5a, 1b-2d, 4b, 4d-5d, 4e and 41 have been screened for antibacterial effects on bacteria and for antifungal activity against yeast strains. The compounds 1b and 4b showed antimicrobial activity against three species of bacteria, Bacillus subtilis, Bacillus cereus and Staphylococcus aureus, and two fungi, Candida albicans and Candida tropicalis. Minimum inhibitory concentrations (MIC) were determined for 1b and 4b. The MIC values were found to be 5000 mu M for each bacteria. The most effective compound, 4b has exhibited activity with a MIC of 312 mu M for C albicans and 625 mu M for C. tropicalis. DNA-binding and the nature of the interaction with pBR322 plasmid DNA are studied. All of the compounds induce changes on the DNA mobility and intensity. Prevention of Hind[l] digestion with the compounds indicates that the compounds bind with AT nucleotides in DNA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.08.035
• 作为产物：
  描述：

  对氟苯甲醛 在 reducting agent 作用下， 以 甲醇 为溶剂， 生成 N,N'-Bis(4-fluorobenzyl)propane-1,3-diamine
  参考文献：
  名称：

  Phosphorus–nitrogen compounds part 22. Syntheses, structural investigations, biological activities and DNA interactions of new mono and bis (4-fluorobenzyl) spirocyclophosphazenes

  摘要：

  The reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with mono (1 and 2) and bis(4-fluorobenzyl) diamines (3-5), FPhCH2NH(CH2)(n)NHR (R=H or FPhCH2-), produce mono (1a and 2a) and bis(4-fluorobenzyl) monospirocyclophosphazenes (3a-5a). The tetraaminomonospirocyclophosphazenes (1b-2d) are obtained from the reactions of the partly substituted phosphazenes (1a and 2a) with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The tetrachlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4a and 5a) with excess pyrrolidine, morpholine and DASD afford the fully substituted bis(4-fluorobenzyl) monospirocyclophosphazenes (4b, 4d-5d) in boiling THF. In addition, monochlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4e and 41) have also been isolated from the reactions with excess morpholine and DASD in boiling THF. The structural investigations of the compounds have been verified by elemental analyses, MS. FTIR, H-1, C-13, F-19 (for 1d and 2d). P-31 NMR, HSQC and HMBC techniques. The crystal structures of 3a, 4a, 5a and 2b have been determined by X-ray crystallography. The compounds 2a-5a, 1b-2d, 4b, 4d-5d, 4e and 41 have been screened for antibacterial effects on bacteria and for antifungal activity against yeast strains. The compounds 1b and 4b showed antimicrobial activity against three species of bacteria, Bacillus subtilis, Bacillus cereus and Staphylococcus aureus, and two fungi, Candida albicans and Candida tropicalis. Minimum inhibitory concentrations (MIC) were determined for 1b and 4b. The MIC values were found to be 5000 mu M for each bacteria. The most effective compound, 4b has exhibited activity with a MIC of 312 mu M for C albicans and 625 mu M for C. tropicalis. DNA-binding and the nature of the interaction with pBR322 plasmid DNA are studied. All of the compounds induce changes on the DNA mobility and intensity. Prevention of Hind[l] digestion with the compounds indicates that the compounds bind with AT nucleotides in DNA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.08.035

文献信息

• Phosphorus–nitrogen compounds: part 70. Syntheses of tetraaminomono/bis(4-fluorobenzyl)spiro(<i>N</i>/<i>N</i>)cyclotriphosphazenes: structural characterization, Hirshfeld surface analysis and comparative evaluation of esterase activities of hCA I and hCA II isoenzymes
  作者：Aytuğ Okumuş、Gamze Elmas、Arzu Binici、Ekrem Tunca、Tuncer Hökelek、Zeynel Kılıç

  DOI：10.1039/d3nj00721a

  日期：——

  data identified the structures of the new products. In addition, the solid-state structure of 2b was confirmed by X-ray crystallography. Hirshfeld surface analysis of 2b indicates that the most important contributions for the crystal packing are from H⋯H (61.2%), H⋯C/C⋯H (24.8%) and H⋯F/F⋯H (9.3%) interactions. On the other hand, the inhibitory effects of these cyclotriphosphazenes on the esterase activities

  通过六氯环三磷腈、N 3 P 3 Cl 6（三聚体；HCCP ）与N -（ 4-氟苄基)-1,3-二氨基丙烷( L1 )和N , N'-双(4-氟苄基)-1,3-二氨基丙烷( L2 )。四氨基单-( 1a和1b ) 和双-(4-氟苄基)螺( N / N)环三磷腈 ( 2a和2b ) 分别由螺1和2与过量的乙基哌嗪和苯基哌嗪在沸腾的 THF 中进行缩合反应制备。元素分析、FTIR、ESI-MS、31 P、13 C 和1 H NMR 数据确定了新产品的结构。此外，通过X射线晶体学证实了2b的固态结构。2b的 Hirshfeld 表面分析表明对晶体堆积最重要的贡献来自 H⋯H（61.2%）、H⋯C/C⋯H（24.8%）和 H⋯F/F⋯H（9.3%）相互作用。另一方面，在体外研究了这些环三磷腈对 hCA I 和 hCA II 同工酶的酯酶活性的抑制作用。确定化合物2b表现出比化合物2a更强的抑制作用。