N-(4-fluorobenzyl)-N'-ethylethane-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'-ethylethane-1,2-diamine
• 英文别名: N-ethyl-N'-(4-fluorobenzyl)-1,2-ethandiamine；N-(4-florobenzyl)-N'-ethyl-1,2-diaminoethane；N-ethyl-N'-(4-fluorobenzyl)-1,2-diaminoethane；N-ethyl-N'-[(4-fluorophenyl)methyl]ethane-1,2-diamine
• 化学式: C₁₁H₁₇FN₂
• 分子量: 196.268
• InChiKey: GSMNYBWEJDLNHQ-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：
  0.45
• 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'-ethylethane-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83%的产率得到7,7,9,9-Tetrachloro-1-ethyl-4-[(4-fluorophenyl)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82%的产率得到N-(4-fluorobenzyl)-N'-ethylethane-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
• 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
• Phosphorus–nitrogen compounds. Part 64. Comparative reactions of spiro and ansa (N/O) cyclotetraphosphazenes with bulky (4-fluorobenzyl) N/N and N/O donor type bidentate reagents: structure, stereogenic properties and cytotoxic activity studies
  作者：Gamze Elmas、Arzu Binici、Mehtap Yakut、Aytuğ Okumuş、Zeynel Kılıç、Bünyemin Çoşut、Tuncer Hökelek、Nebahat Aytuna Çerçi、Leyla Açık

  DOI：10.1039/d2nj02280j

  日期：——

  iro(N/O) (ansa-2b) and 2-cis-4-dichloro-ansa-6-trans-8-dispiro(N/O) (ansa-2c). The reactions of 2,4-ansa (3) with excess L2 led to the formation of 2-cis-4-dichloro-ansa-2-trans-6-spiro(N/N) (trans-3a) and 2-cis-4-dichloro-ansa-2-cis-6-spiro(N/N) (cis-3a) cyclotetraphosphazenes. However, the reactions of 2,4-ansa (3) with excess L3 afforded monospiro 2-cis-4-dichloro-ansa-4-trans-6-spiro(N/O) (trans-3b)

  八氯环四磷腈 N 4 P 4 Cl 8 ( 1 ) ( OCCP , 四聚体) 与等摩尔量的 3-( N - 二茂铁基甲基氨基)-1-丙醇钠 ( L1 ) 反应生成二茂铁基-螺-( 2 )和二茂铁基-2-顺-4-二氯-ansa-( 3 )环四磷腈。两种起始化合物都用于生产新的无机-有机杂化多杂环螺环和 ansa 环四磷腈。Spiro ( 2 ) 用过量的N -(4-fluorobenzyl) -N '-ethyl-1,2-diaminoethane (L2 )得到2-反式-6-二螺环(反式-2a )和2-反式-4-顺-6-反式-8-四螺环(四螺环-2a )环四磷腈。螺环 ( 2 ) 也与过量的 3-(4-氟苄氨基)-1-丙醇钠 ( L3 ) 反应生成 2-反式-6- 双螺环 ( trans -2b )、2-顺-6- 双螺环 ( cis -2b ) ), 2- cis -4- trans -6-trispiro
• Phosphorus–nitrogen compounds. Part 73. Dispiromono and dispirobicyclotetraphosphazene derivatives: syntheses, and spectroscopic, crystallographic and thermal studies
  作者：Gamze Elmas、Aytuğ Okumuş、Zeynel Kılıç、Tuncer Hökelek

  DOI：10.1039/d4nj00569d

  日期：——

  Reactions of octachlorocyclotetraphosphazene (OCCP), N4P4Cl8 (1), with two equimolar amounts of N-ethyl-N′-(4-fluorobenzyl)-1,2-diaminoethane (L1) gave the trans-monocyclic-(2) and cis-monocyclic-(3) bis(ethyl-4-fluorobenzylspiro)cyclotetraphosphazenes. The obtained trans-monocyclic-bis-(2) reacted separately with excess n-propyl and iso-propylamines to afford the monocyclic (4c and 4d) and bicyclic

  八氯环四磷腈 ( OCCP )、N 4 P 4 Cl 8 ( 1 ) 与两等摩尔量的N -乙基-N ' -(4-氟苄基)-1,2-二氨基乙烷 ( L1 ) 反应，得到反式-单环-( 2 )和顺式-单环-( 3 )双(乙基-4-氟苄基螺)环四磷腈。获得的反式单环双-( 2 )分别与过量的正丙胺和异丙胺反应，分别得到单环( 4c和4d )和双环( 5b和5c )环四磷腈。还研究了反式单环双( 2 )与正丙胺以1:1/1:2摩尔比的反应，以阐明双环磷腈的形成途径。形成三氯-正丙氨基-( 4a )、二氯-双(正丙氨基)-( 4b )和一氯-2-反式-6-双(4-氟苄基螺)二环-( 5a )四磷腈。因此，确定了2的四聚体环中有多少Cl原子被胺取代，并提出了形成双环产物的途径。此外，顺式单环双( 3 )的反应仅用过量的正丙胺进行。获得单环-( 6a )和双环-( 7a )环四磷腈。对新型磷腈进行了光谱、晶体学（2和4c