4,4,6,6-tetrachloro-3-methyl-3,4-dihydrospiro[1.3.2]benzoxazaphosphorine[2λ5,4λ5,6λ5][1,3,5,2,4,6]triazatriphosphorine | 1236129-59-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4,4,6,6-tetrachloro-3-methyl-3,4-dihydrospiro[1.3.2]benzoxazaphosphorine[2λ5,4λ5,6λ5][1,3,5,2,4,6]triazatriphosphorine
• 英文别名: (2R)-4,4,6,6-tetrachloro-3'-methylspiro[1,3,5-triaza-2lambda5,4lambda5,6lambda5-triphosphacyclohexa-1,3,5-triene-2,2'-4H-1,3,2lambda5-benzoxazaphosphinine]；(2R)-4,4,6,6-tetrachloro-3'-methylspiro[1,3,5-triaza-2λ5,4λ5,6λ5-triphosphacyclohexa-1,3,5-triene-2,2'-4H-1,3,2λ5-benzoxazaphosphinine]
• CAS: 1236129-59-1
• 化学式: C₈H₉Cl₄N₄OP₃
• 分子量: 411.919
• InChiKey: HNMFEFDAEJQFGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基-N-甲基苄胺盐酸盐 在 六氯环三磷腈 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以78%的产率得到4,4,6,6-tetrachloro-3-methyl-3,4-dihydrospiro[1.3.2]benzoxazaphosphorine[2λ5,4λ5,6λ5][1,3,5,2,4,6]triazatriphosphorine
  参考文献：
  名称：

  Phosphorus−Nitrogen Compounds. 21. Syntheses, Structural Investigations, Biological Activities, and DNA Interactions of New N/O Spirocyclic Phosphazene Derivatives. The NMR Behaviors of Chiral Phosphazenes with Stereogenic Centers upon the Addition of Chiral Solvating Agents

  摘要：

  The reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N/O-donor-type N-alkyl (or aryl)-o-hydroxybenzylamines (la-le) produce mono- (2a-2e), di- (3a-3d), and tri- (4a and 4b) spirocyclic phosphazenes. The tetrapyrrolidino monospirocyclic phosphazenes (2f-2i) are prepared from the reactions of partly substituted compounds (2a-2d) with excess pyrrolidine. The dispirodipyrrolidinophosphazenes (3e-3h) and trispirophosphazenes (3i-3k) are obtained from the reactions of trans-dispirophosphazenes with excess pyrrolidine and sodium (3-amino-1-propanoxide), respectively. Compounds 3a-3d have cis and trans geometric isomers. Only the trans isomers of these compounds are isolated. Compounds 3a-3h have two stereogenic P atoms. They are expected to be in cis (meso) and trans (racemic) geometric isomers. In the trans trispiro compounds (3i-3k), there are three stereogenic P atoms. They are expected to be in racemic mixtures. The stereogenic properties of 3a-3k are confirmed by P-31 NMR spectroscopy upon the addition of the chiral solvating agent; (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol. The molecular structures of 3i-3k, 4a, and 4b look similar to a propeller, where the chemical environment of one P atom is different from that of others. Additionally, 4a and 4b are also expected to exist as cis-trans-trans and cis-cis-cis geometric isomers, but both of them are found to be in cis-trans-trans geometries. The solid-state structures of 2a, 2e, 2f, 3e, and 31 are determined by X-ray crystallography. The compounds 2f-2i, 3e-3i, and 3k are screened for antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against yeast strains. These compounds (except 3f) have shown a strong affinity against most of the bacteria. Minimum inhibitory concentrations (MIC) are determined for 2f-2i, 3e-3i, and 3k. DNA binding and the nature of interaction with pUC18 plasmid DNA are studied. The compounds 2f-2i, 3e-3i, and 3k induce changes on the DNA mobility. The prevention of BamHI and HindIII digestion (except 2g) with compounds indicates that the compounds bind with nucleotides in DNA.

  DOI：

  10.1021/ic100781v

文献信息

• Phosphorus−Nitrogen Compounds. 21. Syntheses, Structural Investigations, Biological Activities, and DNA Interactions of New N/O Spirocyclic Phosphazene Derivatives. The NMR Behaviors of Chiral Phosphazenes with Stereogenic Centers upon the Addition of Chiral Solvating Agents
  作者：Muhammet Işıklan、Nuran Asmafiliz、Ezgi Elif Özalp、Elif Ece İlter、Zeynel Kılıç、Bünyemin Çoşut、Serkan Yeşilot、Adem Kılıç、Aslı Öztürk、Tuncer Hökelek、L. Yasemin Koç Bilir、Leyla Açık、Emel Akyüz

  DOI：10.1021/ic100781v

  日期：2010.8.2

  The reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N/O-donor-type N-alkyl (or aryl)-o-hydroxybenzylamines (la-le) produce mono- (2a-2e), di- (3a-3d), and tri- (4a and 4b) spirocyclic phosphazenes. The tetrapyrrolidino monospirocyclic phosphazenes (2f-2i) are prepared from the reactions of partly substituted compounds (2a-2d) with excess pyrrolidine. The dispirodipyrrolidinophosphazenes (3e-3h) and trispirophosphazenes (3i-3k) are obtained from the reactions of trans-dispirophosphazenes with excess pyrrolidine and sodium (3-amino-1-propanoxide), respectively. Compounds 3a-3d have cis and trans geometric isomers. Only the trans isomers of these compounds are isolated. Compounds 3a-3h have two stereogenic P atoms. They are expected to be in cis (meso) and trans (racemic) geometric isomers. In the trans trispiro compounds (3i-3k), there are three stereogenic P atoms. They are expected to be in racemic mixtures. The stereogenic properties of 3a-3k are confirmed by P-31 NMR spectroscopy upon the addition of the chiral solvating agent; (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol. The molecular structures of 3i-3k, 4a, and 4b look similar to a propeller, where the chemical environment of one P atom is different from that of others. Additionally, 4a and 4b are also expected to exist as cis-trans-trans and cis-cis-cis geometric isomers, but both of them are found to be in cis-trans-trans geometries. The solid-state structures of 2a, 2e, 2f, 3e, and 31 are determined by X-ray crystallography. The compounds 2f-2i, 3e-3i, and 3k are screened for antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against yeast strains. These compounds (except 3f) have shown a strong affinity against most of the bacteria. Minimum inhibitory concentrations (MIC) are determined for 2f-2i, 3e-3i, and 3k. DNA binding and the nature of interaction with pUC18 plasmid DNA are studied. The compounds 2f-2i, 3e-3i, and 3k induce changes on the DNA mobility. The prevention of BamHI and HindIII digestion (except 2g) with compounds indicates that the compounds bind with nucleotides in DNA.