spiro[3-(N-ferrocenylmethylamino)-1-propanoxy]-4,4,6,6-tetrachlorocyclotriphosphazatriene | 1253964-15-6

• 英文名称: spiro[3-(N-ferrocenylmethylamino)-1-propanoxy]-4,4,6,6-tetrachlorocyclotriphosphazatriene
• CAS: 1253964-15-6
• 化学式: C₁₄H₁₇Cl₄FeN₄OP₃
• 分子量: 547.895
• InChiKey: NSUYTCFUCXAGME-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：

  四氢吡咯 、 spiro[3-(N-ferrocenylmethylamino)-1-propanoxy]-4,4,6,6-tetrachlorocyclotriphosphazatriene 在 N(C₂H₅)3 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到spiro[3-(N-ferrocenylmethylamino)-1-propanoxy]-4,4,6,6-tetrapyrrolidinocyclotriphosphazatriene
  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：

  六氯环三磷腈 、 sodium 3-(N-ferrocenylmethylamino)-1-propanoxide 在 N(C₂H₅)3 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到spiro[3-(N-ferrocenylmethylamino)-1-propanoxy]-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

文献信息

• Phosphorus-nitrogen compounds: Part 43. Syntheses, spectroscopic characterizations and antimicrobial activities of cis- and trans-N/O dispirocyclotriphosphazenes containing ferrocenyl pendant arms
  作者：Yasemin Tümer、Nuran Asmafiliz、Zeynel Kılıç、Betül Aydın、Leyla Açık、Tuncer Hökelek

  DOI：10.1016/j.molstruc.2018.07.050

  日期：2018.12

  and 4) were also isolated from the reaction mixtures as by-products. The characterizations of the new compounds (5–8) were elucidated using MS, FTIR and 1H, 13C and 31P NMR techniques. The molecular structure of 6 was established by X-ray crystallography. As expected, compounds 5, 6, 7 and 8 have two stereogenic P-atoms. The compounds 5 and 6 are likely to be in cis (meso) forms, whereas the compounds

  摘要 六氯环三磷腈 N3P3Cl6 与配体的两种等摩尔量的钠盐反应合成了含有二茂铁基悬臂的顺式（5 和 6）和反式二螺二茂二茂铁基磷腈（7 和 8）；[2-(N-二茂铁基甲基氨基)-1-乙氧化物(1)和3-(N-二茂铁基甲氨基)-1-丙氧化物(2)]。单螺二茂铁基环三磷腈（3和4）也作为副产物从反应混合物中分离出来。使用 MS、FTIR 和 1H、13C 和 31P NMR 技术阐明了新化合物 (5-8) 的表征。6的分子结构是通过X射线晶体学确定的。正如预期的那样，化合物 5、6、7 和 8 具有两个立体 P 原子。化合物 5 和 6 可能呈顺式（内消旋）形式，而化合物 7 和 8 呈反式（外消旋）形式。除了，评估了环三磷腈对 G(+) 和 G(-) 细菌和真菌的抗菌活性。还研究了化合物与 pBR322 质粒 DNA 的相互作用。
• Phosphorus–nitrogen compounds. Part 41. Ferrocenyl pendant-armed spirocyclopiperidinocyclotriphosphazatrienes: Langmuir–Blodgett thin films and biological activity studies
  作者：Nuran Asmafiliz、Mehmet Civan、Neşe Uzunalioğlu、Arda Özben、Zeynel Kiliç、Hande Kayalak、Leyla Açik、Tuncer Hökelek

  DOI：10.1007/s12039-018-1545-x

  日期：2018.11

  structures of all the new compounds were determined using spectroscopic techniques. The ultrathin Langmuir–Blodgett (LB) films of two compounds (3 and 12) were prepared. The characterization of the LB films using p-polarized grazing angle (GAIR) and horizontal attenuated total reflectance (HATR) techniques was carried out. The molecular and crystal structure of the compound 6 was examined using X-ray crystallography

  抽象的N / N或N / O螺monoferrocenylcyclotriphosphazatrienes（该氯置换反应15）与哌啶导致geminal-（6 - 10）和四- piperidinophosphazenes与monoferrocenyl挂件臂（11 - 15）。所有新化合物的结构均使用光谱技术确定。准备了两种化合物（3和12）的超薄Langmuir-Blodgett（LB）膜。使用p偏振掠角（GAIR）和水平衰减全反射（HATR）技术对LB膜进行了表征。化合物6的分子和晶体结构用X射线晶体学检查。此外，六种化合物（之间的相互作用6，7，11，12，14和15）和pBR322的质粒DNA通过琼脂糖凝胶电泳分析。 图形概要 内容提要制备了其中两种化合物的超薄Langmuir-Blodgett（LB）膜。确定了代表性实例的分子和晶体结构。另外，通过琼脂糖凝胶电泳研究了其中一些与pBR322质粒DNA之间的相互作用。
• Phosphorus-nitrogen compounds. Part 39. Syntheses and Langmuir-Blodgett thin films and antimicrobial activities of N/N and N/O spirocyclotriphosphazenes with monoferrocenyl pendant arm
  作者：Nuran Asmafiliz、Mehmet Civan、Arda Özben、Zeynel Kılıç、Nagehan Ramazanoğlu、Leyla Açık、Tuncer Hökelek

  DOI：10.1002/aoc.4223

  日期：2018.4

  The Cl substitution reactions of the N/N (1‐3) and N/O (4 and 5) spirocyclic monoferrocenylphosphazenes with 1,4‐dioxa‐8‐azaspiro[4,5]decane (DASD) produce the mono‐ (1a‐5a), geminal‐ (1b‐5b) and tetrakis‐DASD‐substituted ferrocenylspirocyclotriphosphazenes (1c‐5c). The mono‐ and geminal‐DASD‐substituted phosphazenes have two and one stereogenic P‐centers, respectively. The structures of the compounds

  在N / N的氯取代反应（1 - 3）和N / O（4和5）的螺环monoferrocenylphosphazenes与1,4-二氧杂-8-氮杂螺[4,5]癸烷（DASD）产生单- （1A ‐ 5a），双生的（1b ‐ 5b）和四-DASD取代的二茂铁基螺环三磷腈（1c ‐ 5c）。单-和双-DASD取代的磷腈分别具有两个和一个立体立体P中心。通过光谱技术确定化合物的结构。3a和2b的分子结构用X射线晶体学评估。此外，还制备了3a和2b的超薄且有序的Langmuir-Blodgett（LB）膜。LB膜的表征使用p偏振掠角（GAIR）和水平衰减全反射（HATR）技术完成。另一方面，研究了八种磷腈衍生物对G（+）和G（-）细菌和真菌的抗菌活性。此外，通过琼脂糖凝胶电泳研究了化合物与质粒DNA之间的相互作用。