spiro(butane-1,4-diamino)[N,N'-bis(1-ferrocenylmethyl)]-4,4,6,6-tetrachlorocyclotriphosphazatriene | 1193342-75-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: spiro(butane-1,4-diamino)[N,N'-bis(1-ferrocenylmethyl)]-4,4,6,6-tetrachlorocyclotriphosphazatriene
• 英文别名: cyclopenta-1,3-diene;iron(2+);2,2,4,4-tetrachloro-7,12-bis(cyclopenta-2,4-dien-1-ylmethyl)-1,3,5,7,12-pentaza-2λ5,4λ5,6λ5-triphosphaspiro[5.6]dodeca-1(6),2,4-triene
• CAS: 1193342-75-4
• 化学式: C₂₆H₃₀Cl₄Fe₂N₅P₃
• 分子量: 758.985
• InChiKey: OYTHQANMXSKAAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.84
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  spiro(butane-1,4-diamino)[N,N'-bis(1-ferrocenylmethyl)]-4,4,6,6-tetrachlorocyclotriphosphazatriene 、 香草醛 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以68%的产率得到4,4′,4″,4′″-[(7,11-diferrocenyl-1,3,5,7,12-pentaaza-2λ⁵,4λ⁵,6λ⁵-triphosphaspiro[6.5]dodeca-1,3,5-triene-2,4,4,4-tetrayl)tetrakis(oxy)]tetrakis(3-methoxybenzaldehyde)
  参考文献：
  名称：

  Phosphorus–nitrogen compounds: Part 28. Syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing vanillinato and pendant ferrocenyl groups

  摘要：

  The gradually Cl replacement reactions of spirocyclic mono (1 and 2) and bisferrocenyl cyclotriphosphazenes (3-5) with the potassium salt of 4-hydroxy-3-methoxybenzaldehyde (potassium vanillinate) gave mono (1a-5a), geminal (gem-1b-5b), non-geminal (cis-1b, cis-5b and trans-2b-5b), tri (1c-5c) and tetra-substituted phosphazenes (1d-5d). Some phosphazenes have stereogenic P-center(s). The chirality of 4c was verified using chiral HPLC column. Electrochemical behaviors were influenced only by the number of ferrocene groups, but not the length of the amine chains and the substituent(s). The structures of the new phosphazenes were determined by FTIR, MS, H-1, C-13 and P-31 NMR, HSQC and HMBC spectral data. The solid-state structures of cis-1b and 4d were examined by single crystal X-ray diffraction techniques. The twelve phosphazene derivatives were screened for antimicrobial activity and the compounds 5a, cis-1b and 2c exhibited the highest antibacterial activity against G(+) and G(-) bacteria. In addition, it was found that overall gem-1b inhibited the growth of Mycobacterium tuberculosis. The compounds 1d, 2d and 4d were tested in HeLa cancer cell lines. Among these compounds, 2d had cytotoxic effect on HeLa cell in the first 48 h. Moreover, interactions between compounds 2a, gem-1b, gem-2b, cis-1b, 2c, 3c, 4c, 5c, 1d, 2d and 4d, and pBR322 plasmid DNA were investigated. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.06.036
• 作为产物：
  描述：

  六氯环三磷腈 、 在 N(CH₂CH₃)3 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 以53%的产率得到spiro(butane-1,4-diamino)[N,N'-bis(1-ferrocenylmethyl)]-4,4,6,6-tetrachlorocyclotriphosphazatriene
  参考文献：
  名称：

  磷氮化合物。18.新型螺环单-和双-二茂铁基磷腈衍生物的合成，立体异构性质，结构和电化学研究，生物学活性和DNA相互作用

  摘要：

  hexachlorocyclotriphosphazatriene的反应中，N 3 P 3氯6，具有单- （1和2）和bisferrocenyldiamines（3 - 5），FCCH 2 NH（CH 2）Ñ NHR 1（R 1 = H或FCCH 2 - ），产生单- （6和7）和螺bisferrocenylphosphazenes（8 - 10）。完全取代的磷腈（11 - 15和18 - 21）从对应的部分取代的磷腈（的反应得到的6 - 10）与过量的吡咯烷和NH 2（CH 2）3分别ONA。的反应6用1-氮杂-12-冠-4，得到偕（16）和三（17）的冠醚取代的磷腈。化合物的结构研究已通过元素分析，质谱，傅里叶变换IR，1 H，13 C和31 P NMR以及DEPT，COSY，HETCOR和HMBC技术进行了验证。的晶体结构7，10，11，并且已经通过X射线晶体学确定了15。在16和1

  DOI：

  10.1021/ic901039k

文献信息

• Syntheses of Chiral Phosphazenes with Stereogenic Centers: NMR Behavior in the Presence of a Chiral Solvating Agent
  作者：Nuran Asmafiliz

  DOI：10.1002/hc.21139

  日期：2014.3

  morpholine, the corresponding geminal–phosphazenes (1b–5b) were isolated. In addition, the condensation reactions of 1 equiv of 1–5 and 3 equiv of morpholine resulted in the formation of di-(1b–5b), tri-(2c–5c), and tetra-substituted phosphazenes. The tri-substituted compounds were isolated as major products. Some new phosphazenes have stereogenic P center(s). The stereogenic properties of 1a and 2c were investigated

  四氯单（1和2）和双二茂铁基螺环三磷腈（3-5）与吗啉在四氢呋喃中的缩合反应得到部分吗啉取代的二茂铁基磷腈。当反应用等量的 1-5 和吗啉进行时，单取代的二茂铁基磷腈 (1a, 3a-5a) 作为主要产物形成。虽然反应是用 1 当量的 1-5 和 2 当量的吗啉进行的，但相应的孪晶磷腈 (1b-5b) 被分离出来。此外，1 当量 1-5 和 3 当量吗啉的缩合反应导致形成二-(1b-5b)、三-(2c-5c) 和四取代的磷腈。三取代的化合物被分离为主要产物。一些新的磷腈具有立体的 P 中心。在手性溶剂化剂的存在下，使用 31P 核磁共振 (NMR) 光谱研究了 1a 和 2c 的立体特性；(S)-(+)-2,2,2-三氟-1-(9'-蒽基)乙醇。所有磷腈的结构均通过一维 1H、13C 和 31P NMR 以及二维异核单量子相干光谱数据进行表征。展示了磷腈的显着光谱特性。
• Phosphorus-Nitrogen Compounds: Part 25. Syntheses, Spectroscopic, Structural and Electrochemical Investigations, Antimicrobial Activities, and DNA Interactions of Ferrocenyldiaminocyclotriphosphazenes
  作者：Nuran Asmafiliz、Zeynel Kılıç、Aslı Öztürk、Yasemin Süzen、Tuncer Hökelek、Leyla Açık、Z. Betül Çelik、L. Yasemin Koç、Mehmet Lütfi Yola、Zafer Üstündağ

  DOI：10.1080/10426507.2013.779273

  日期：2013.12.1

  The condensation reactions of hexachlorocyclotriphosphazene (N3P3Cl6) with mono (1 and 2) and bisferrocenyldiamines (3-5 and 7) resulted in the formation of tetrachloro mono- (8 and 9) and bisferrocenylspirocyclotriphosphazenes (10-13). In addition the tetramorpholino mono- (8a and 9a) and bisferrocenylphosphazenes (10a-12a) were obtained from the reactions of the corresponding tetrachlorophosphazenes (8-12) with excess morpholine. The structures of all the phosphazenes were determined using FTIR, MS, H-1, C-13, and P-31 NMR and 2-dimensional NMR techniques. The structures of 9a and 13 were determined by single crystal X-ray diffraction techniques. Cyclic voltammetric investigations of compounds 8a, 9a, and 11a revealed that ferrocene redox centers undergo reversible oxidation. These ferrocenylphosphazenes appear to be quite robust electrochemically. Interactions between the compounds 8a, 9a, 11a, and 12a and pBR322 plasmid DNA were investigated by agarose gel electrophoresis. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]
• Phosphorus–nitrogen compounds: Part 26. Syntheses, spectroscopic and structural investigations, biological and cytotoxic activities, and DNA interactions of mono and bisferrocenylspirocyclotriphosphazenes
  作者：Nuran Asmafiliz、Zeynel Kılıç、Tuncer Hökelek、L. Yasemin Koç、Leyla Açık、Yasemin Süzen、Yağmur Öner

  DOI：10.1016/j.ica.2013.03.001

  日期：2013.5

  The condensation reactions of the tetrachloro mono (1 and 2) and bisferrocenylspirocyclotriphosphazenes (3-5) with 1,4-dioxa-8-azaspiro[4,5]decane (DASD) resulted in the formation of the partly and fully DASD-substituted phosphazenes. The reactions of equal amounts of 1-5 and DASD produced the mono-DASD-substituted ferrocenylphosphazenes (1a-5a), as the major product. When the reactions were carried out with 1 equiv of 1-5 and 2 equiv of DASD, corresponding geminal-phosphazenes (1b-5b) were isolated. Moreover, the reactions of 1 equiv of 1-5 and 3 equiv of DASD gave the tri-(1c-4c) and tetra-substituted (1d-5d) phosphazenes. When the excess DASD was used, the fully-substituted phosphazenes (1d-5d) were obtained. The chirality of 3a was evaluated using chiral HPLC column. The structures of all the phosphazenes were verified by FTIR, MS, H-1, C-13 and P-31 NMR, and HSQC spectral data. The crystal structures of 4a, 2b, 5b, and 1d were determined by X-ray diffraction techniques. The 10 phosphazene derivatives were screened for antimicrobial activity. Meanwhile, interactions between the compounds and pBR322 plasmid DNA were presented by agarose gel electrophoresis. The compounds 2b, 1d, 2d, and 4d were tested against HeLa cancer cell lines. Among these compounds, 4d had cytotoxic effect on HeLa cell after 24 h treatment. (C) 2013 Elsevier B. V. All rights reserved.