2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene

• 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: 2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene
• 英文别名: 2,2-dichloro-4,4,6,6-tetrakis(phenylthio)cyclotriphosphazene；2,2-Dichloro-4,4,6,6-tetrakis(phenylsulfanyl)-1,3,5-triaza-2lambda5,4lambda5,6lambda5-triphosphacyclohexa-1,3,5-triene；2,2-dichloro-4,4,6,6-tetrakis(phenylsulfanyl)-1,3,5-triaza-2λ5,4λ5,6λ5-triphosphacyclohexa-1,3,5-triene
• 化学式: C₂₄H₂₀Cl₂N₃P₃S₄
• 分子量: 642.534
• InChiKey: AJFHDXOSOSCTMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene 、 酚酞 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 144.0h， 以34%的产率得到3,3-Bis[4-[[2-chloro-4,4,6,6-tetrakis(phenylsulfanyl)-5-aza-1,3-diazanida-4lambda5-phospha-2,6-diphosphoniacyclohex-4-en-2-yl]oxy]phenyl]-2-benzofuran-1-one
  参考文献：
  名称：

  Nucleophilic substitution reactions of phenolphthalein with different substituted cyclotriphosphazene derivatives

  摘要：

  In the present work, the partially or fully substituted phenolphthalein bridged cyclotriphosphazene derivatives and their spectral properties were reported for the first time. The reactions of phenolphthalein (2), with racemic trans-2,4-bis(dibenzylamino)-2,4,6,6-tetrachlorocyclotriphosphazene (3), 2,2,4,4-tetra(anilino)-6,6-dichlorocyclotriphosphazene (4), 2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene (5) and 2,2,4,4,6-pentaphenoxy-6-chlorocyclotriphosphazene (6) in THF gave phenolphthalein bridged cyclotriphosphazene compounds 7-10. All these compounds (7-10) were fully characterized by elemental analysis, FT-IR, mass (MS), H-1, C-13 and P-31 NMR, electronic absorption and fluorescence spectroscopies. The fluorescence properties of novel phenolphthalein bridged dibenzylamino, anilino, thiophenoxy and phenoxy substituted cyclotriphosphazene compounds (7-10) were investigated and compared in dichloromethane. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.07.006
• 作为产物：
  描述：

  苯硫酚 在 六氯环三磷腈 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene
  参考文献：
  名称：

  Synthesis of Arylthiochlorocyclotriphosphazenes

  摘要：

  We investigated the reaction between hexachlorocyclotriphosphazene ((NPCl2)(3): HCCP) and thiols in the presence of bases. In MeCN/Et3N, two and/or four arylthio units were introduced in gem-mode selectively by controlling the amount of thiols: thus, HCCP was treated with 2 and/or 4 equivalents of ArSH/Et3N in MeCN to afford 2,2-dithiolated and/or 2,2,4,4-tetrathiolated products, respectively. Neither mono-thiosubstituted products, tri-thiosubstituted products, nor regioisomers (non-geminal products) were obtained. In contrast, when other solvents such as THE and Et2O or other bases such as NaH or K2CO3 were used, a mixture of dithiolated products, tetrathiolated products, and hexathiolated products was obtained.

  DOI：

  10.3987/com-19-14100

文献信息

• Synthesis of N,N-spiro-bridged bis(cyclotriphosphazene) derivatives bearing aryl thio groups and their comparison with alkoxy and amino derivatives
  作者：Ceylan Mutlu Balcı、Duygu Palabıyık、Serap Beşli

  DOI：10.1016/j.ica.2024.121953

  日期：2024.5

  In this study, bis (1a, b) and tetrakis (2a, b) cyclotriphosphazenes containing aryl thio groups were reacted with n-butyl amine. Deprotonation reactions of the obtained mono amino bis phenylthio (3a, b) and bis naphthylthio (4a, b) cyclotriphosphazenes were carried out in the presence of NaH base. New N,N-spiro bridged biscyclotriphosphazenes containing bis geminal phenylthio (5a-I and 5a-II) and

  在本研究中，含有芳硫基的双( 1a，b )和四( 2a，b )环三磷腈与正丁胺反应。所得单氨基双苯硫基( 3a，b )和双萘硫基( 4a，b )环三磷腈在NaH碱存在下进行去质子化反应。产生了含有双偕苯硫基（5a-I和5a-II）和萘硫基（5b-I和5b-II ）基团的新N,N-螺桥双环三磷腈。通过MALDI-TOF、 31 P和1 H NMR光谱以及单晶X射线晶体学（5a-I和5b-I ）对新合成的化合物进行表征。使用紫外/可见光和荧光光谱测定化合物1a、b、2a、b、5a-I和5b-I的光物理性质。同时，对N,N-螺桥双环磷腈的结构与之前合成的含有不同官能团的双环磷腈的结构进行了综合评价。
• Synthesis of Arylthiochlorocyclotriphosphazenes
  作者：Manabu Kuroboshi、Masaki Mikasa、Hideo Tanaka

  DOI：10.3987/com-19-14100

  日期：——

  We investigated the reaction between hexachlorocyclotriphosphazene ((NPCl2)(3): HCCP) and thiols in the presence of bases. In MeCN/Et3N, two and/or four arylthio units were introduced in gem-mode selectively by controlling the amount of thiols: thus, HCCP was treated with 2 and/or 4 equivalents of ArSH/Et3N in MeCN to afford 2,2-dithiolated and/or 2,2,4,4-tetrathiolated products, respectively. Neither mono-thiosubstituted products, tri-thiosubstituted products, nor regioisomers (non-geminal products) were obtained. In contrast, when other solvents such as THE and Et2O or other bases such as NaH or K2CO3 were used, a mixture of dithiolated products, tetrathiolated products, and hexathiolated products was obtained.
• Nucleophilic substitution reactions of phenolphthalein with different substituted cyclotriphosphazene derivatives
  作者：Gönül Yenilmez Çiftçi、Elif Şenkuytu、Mahmut Durmuş、Adem Kılıç

  DOI：10.1016/j.poly.2013.07.006

  日期：2013.10

  In the present work, the partially or fully substituted phenolphthalein bridged cyclotriphosphazene derivatives and their spectral properties were reported for the first time. The reactions of phenolphthalein (2), with racemic trans-2,4-bis(dibenzylamino)-2,4,6,6-tetrachlorocyclotriphosphazene (3), 2,2,4,4-tetra(anilino)-6,6-dichlorocyclotriphosphazene (4), 2,2,4,4-tetrathiophenoxy-6,6-dichlorocyclotriphosphazene (5) and 2,2,4,4,6-pentaphenoxy-6-chlorocyclotriphosphazene (6) in THF gave phenolphthalein bridged cyclotriphosphazene compounds 7-10. All these compounds (7-10) were fully characterized by elemental analysis, FT-IR, mass (MS), H-1, C-13 and P-31 NMR, electronic absorption and fluorescence spectroscopies. The fluorescence properties of novel phenolphthalein bridged dibenzylamino, anilino, thiophenoxy and phenoxy substituted cyclotriphosphazene compounds (7-10) were investigated and compared in dichloromethane. (C) 2013 Elsevier Ltd. All rights reserved.