2,4-(2',2',3',3'-tetrafluoro-1',4'-butanedioxy)-2,4,6,6-tetrachlorocyclotriphosphazatriene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: 2,4-(2',2',3',3'-tetrafluoro-1',4'-butanedioxy)-2,4,6,6-tetrachlorocyclotriphosphazatriene
• 英文别名: 1,8,10,10-Tetrachloro-4,4,5,5-tetrafluoro-2,7-dioxa-9,11,12-triaza-1lambda5,8lambda5,10lambda5-triphosphabicyclo[6.3.1]dodeca-1(12),8,10-triene；1,8,10,10-tetrachloro-4,4,5,5-tetrafluoro-2,7-dioxa-9,11,12-triaza-1λ5,8λ5,10λ5-triphosphabicyclo[6.3.1]dodeca-1(12),8,10-triene
• 化学式: C₄H₄Cl₄F₄N₃O₂P₃
• 分子量: 436.822
• InChiKey: XLPRFGMIUKONIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,4-(2',2',3',3'-tetrafluoro-1',4'-butanedioxy)-2,4,6,6-tetrachlorocyclotriphosphazatriene 、 正丁胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到
  参考文献：
  名称：

  The synthesis and thermal properties of fluorodioxy-substituted N,N-spiro bridged cyclotriphosphazenes

  摘要：

  Fluorodioxy substituted mono-spiro (1a,b), di-spiro (2a,b) and mono-ansa (3a-c) cyclotriphosphazene derivatives were reacted with n-butylamine to obtain fluorodioxy cyclotriphosphazenes bearing a P-NH group. Then, the fluorodioxy cyclotriphosphazene derivatives containing one NH moiety (4a,b; 5a,5b and 6a-c) which can give a deprotonation reaction were treated with sodium hydride giving rise to new types of bis-cyclophosphazenes bridged with a four-membered cyclophosphazane ring in a spiro arrangement (7, 8, 9a,b and 10a-c). The deprotonation reactions of substituted cyclotriphosphazenes were investigated for the first time and rigid and stable spiro- and ansa-derivatives of N,N-spiro bridged biscyclotriphosphazenes were obtained. Additionally, the thermal stabilities of all new compounds were investigated and found that the thermal stability increases with the formation of N,N-spiro bridge. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.01.014
• 作为产物：
  描述：

  四氟丁二醇 在 六氯环三磷腈 作用下， 生成 2,4-(2',2',3',3'-tetrafluoro-1',4'-butanedioxy)-2,4,6,6-tetrachlorocyclotriphosphazatriene 、 1,1-(2',2',3',3'-tetrafluoro-1',4'-butanedioxy)-3,3,5,5-tetrachlorocyclotriphosphazene
  参考文献：
  名称：

  Synthesis, cytotoxicity and apoptosis of cyclotriphosphazene compounds as anti-cancer agents

  摘要：

  In the present study, a number of new dispirobino and dispiroansa spermine derivatives of cyclotriphosphazene (8-10, 13) were synthesized and characterized by elemental analysis, mass spectrometry, H-1 and P-31 NMR spectroscopy. At first, in vitro cytotoxic activity of cyclotriphosphazene compounds (1-14) against HT-29 (human colon adenocarcinoma), Hep2 (Human epidermoid larynx carcinoma), and Vero (African green monkey kidney) cell lines was investigated. Our study showed that most of these compounds stimulate apoptosis and they have cytotoxic effects for HT-29 and Hep2 cells. Additionally, these compounds (1-14) were investigated for their antibacterial activity against gram-positive (Staphylococcus aureus), gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria and for their antifungal activity against Candida albicans, and were shown to be inactive. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.018

文献信息

• Retention of Configuration in the Nucleophilic Substitution Reactions of Some Nine-Membered Ansa Derivatives of Cyclotriphosphazatriene
  作者：Serap Beşli、Simon J. Coles、David B. Davies、Michael B. Hursthouse、Hanife İbişo??lu、Adem Kılıç、Robert A. Shaw

  DOI：10.1002/chem.200400311

  日期：2004.10.4

  X-ray crystallographic evidence shows that nucleophilic substitution reactions of two different types of cyclophosphazene derivatives with relatively rigid nine-membered ansa rings leads to the first demonstration of retention of configuration in these molecular systems.

  X射线晶体学证据表明，两种不同类型的环磷腈衍生物具有相对刚性的九元ansa环的亲核取代反应导致这些分子系统中构型的保留首次得到证明。
• The synthesis and thermal properties of fluorodioxy-substituted N,N-spiro bridged cyclotriphosphazenes
  作者：Ceylan Mutlu Balcı、Serap Beşli

  DOI：10.1016/j.poly.2017.01.014

  日期：2017.4

  Fluorodioxy substituted mono-spiro (1a,b), di-spiro (2a,b) and mono-ansa (3a-c) cyclotriphosphazene derivatives were reacted with n-butylamine to obtain fluorodioxy cyclotriphosphazenes bearing a P-NH group. Then, the fluorodioxy cyclotriphosphazene derivatives containing one NH moiety (4a,b; 5a,5b and 6a-c) which can give a deprotonation reaction were treated with sodium hydride giving rise to new types of bis-cyclophosphazenes bridged with a four-membered cyclophosphazane ring in a spiro arrangement (7, 8, 9a,b and 10a-c). The deprotonation reactions of substituted cyclotriphosphazenes were investigated for the first time and rigid and stable spiro- and ansa-derivatives of N,N-spiro bridged biscyclotriphosphazenes were obtained. Additionally, the thermal stabilities of all new compounds were investigated and found that the thermal stability increases with the formation of N,N-spiro bridge. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthesis, cytotoxicity and apoptosis of cyclotriphosphazene compounds as anti-cancer agents
  作者：Tuba Yıldırım、Kemal Bilgin、Gönül Yenilmez Çiftçi、Esra Tanrıverdi Eçik、Elif Şenkuytu、Yıldız Uludağ、Leman Tomak、Adem Kılıç

  DOI：10.1016/j.ejmech.2012.03.018

  日期：2012.6

  In the present study, a number of new dispirobino and dispiroansa spermine derivatives of cyclotriphosphazene (8-10, 13) were synthesized and characterized by elemental analysis, mass spectrometry, H-1 and P-31 NMR spectroscopy. At first, in vitro cytotoxic activity of cyclotriphosphazene compounds (1-14) against HT-29 (human colon adenocarcinoma), Hep2 (Human epidermoid larynx carcinoma), and Vero (African green monkey kidney) cell lines was investigated. Our study showed that most of these compounds stimulate apoptosis and they have cytotoxic effects for HT-29 and Hep2 cells. Additionally, these compounds (1-14) were investigated for their antibacterial activity against gram-positive (Staphylococcus aureus), gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria and for their antifungal activity against Candida albicans, and were shown to be inactive. (C) 2012 Elsevier Masson SAS. All rights reserved.