2-oxo-4-phenyl-2,5,6,7,8-pentachlorobenzo[e]-1,2,λ⁵(2H)-oxaphosphorine | 515836-36-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-oxo-4-phenyl-2,5,6,7,8-pentachlorobenzo[e]-1,2,λ⁵(2H)-oxaphosphorine
• 英文别名: 2H-1,2-Benzoxaphosphorin, 2,5,6,7,8-pentachloro-4-phenyl-, 2-oxide；2,5,6,7,8-pentachloro-4-phenyl-1,2λ5-benzoxaphosphinine 2-oxide
• CAS: 515836-36-9
• 化学式: C₁₄H₆Cl₅O₂P
• 分子量: 414.439
• InChiKey: VRRXATSMGWOVDE-UHFFFAOYSA-N

物化性质

• 熔点：
  179-181 °C(Solv: chloroform (67-66-3))
• 沸点：
  503.2±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-oxo-4-phenyl-2,5,6,7,8-pentachlorobenzo[e]-1,2,λ⁵(2H)-oxaphosphorine 在 水 作用下， 生成 2-(2-hydroxy-3,4,5,6-tetrachlorophenyl)-2-phenylvinylphosphonic acid
  参考文献：
  名称：

  摘要：

  As shown by NMR and IR spectroscopy and high-resolution mass spectrometry, the major products of the reaction of 2,2,2,4,5,6,7-heptachlorobenzo[d]-1,3,2lambda(5)-dioxaphosphole with phenylacetylene are a six-membered heterocyclic compound, 2-oxo-4-phenyl-2,5,6,7,8-pentachlorobenzo[e]-1,2,5(2H)-oxaphosphorine, and the E and Z isomers of 2-(2,3,4,4,5-pentachlorocyclohexadienon-6-yl)-2-phenylvinylphosphonic dichloride. The molecular and supramolecular structure of the heterocycle and phosphorus-containing products of its hydrolysis were studied by single crystal X-ray diffraction.

  DOI：

  10.1023/a:1023349414864
• 作为产物：
  描述：

  邻四氯苯醌 在 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-oxo-4-phenyl-2,5,6,7,8-pentachlorobenzo[e]-1,2,λ⁵(2H)-oxaphosphorine
  参考文献：
  名称：

  摘要：

  As shown by NMR and IR spectroscopy and high-resolution mass spectrometry, the major products of the reaction of 2,2,2,4,5,6,7-heptachlorobenzo[d]-1,3,2lambda(5)-dioxaphosphole with phenylacetylene are a six-membered heterocyclic compound, 2-oxo-4-phenyl-2,5,6,7,8-pentachlorobenzo[e]-1,2,5(2H)-oxaphosphorine, and the E and Z isomers of 2-(2,3,4,4,5-pentachlorocyclohexadienon-6-yl)-2-phenylvinylphosphonic dichloride. The molecular and supramolecular structure of the heterocycle and phosphorus-containing products of its hydrolysis were studied by single crystal X-ray diffraction.

  DOI：

  10.1023/a:1023349414864

文献信息

• Reaction of Phenylenedioxytrihalogenophosphoranes with Arylacetylenes. Synthesis and Spatial Structure of the Derivatives of 2-Oxo-4-Aryl-5,6-Benzo-1,2-Oxaphosphorin-2-Enes
  作者：Vladimir F. Mironov、Aidar T. Gubaidullin、Ravil R. Petrov、Igor A. Litvinov、Alfiya A. Shtyrlina、Tatyana A. Zyablikova、Nail M. Azancheev、Alexander I. Konovalov、Rashid Z. Musin

  DOI：10.1080/10426509908546260

  日期：1999.1.1

  New method of synthesis of six-membered heterocycles – 2-R-2-oxo-4-aryl-2H-benzo[e][1,2]-oxaphosphorin-3-enes has been developed. It includes the interaction of arylenedioxy trihalogenophosphoranes with arylacetylenes. The formation of phosphoryl group and P-C bond, ipso-substitution of the aromatic oxygen and halogenation of the benzene ring take place in this unusual reaction. The influence of the

  已开发出合成六元杂环的新方法 - 2-R-2-oxo-4-aryl-2H-benzo[e][1,2]-oxaphosphorin-3-enes。它包括亚芳基二氧基三卤代正膦与芳基乙炔的相互作用。在这个不寻常的反应中发生了磷酰基和 PC 键的形成、芳香氧的同位取代和苯环的卤化。讨论了正膦结构对合成结果的影响。如果正膦苯环的两个对位都被卤素占据，就会产生卤素分子。2-R-2-oxo-4-aryl-2H-benzo[e][1,2]-oxaphosphorin-3-enes 的结构是通过 X 射线分析确定的。
• ——
  作者：V. F. Mironov

  DOI：10.1023/a:1023349414864

  日期：——

  As shown by NMR and IR spectroscopy and high-resolution mass spectrometry, the major products of the reaction of 2,2,2,4,5,6,7-heptachlorobenzo[d]-1,3,2lambda(5)-dioxaphosphole with phenylacetylene are a six-membered heterocyclic compound, 2-oxo-4-phenyl-2,5,6,7,8-pentachlorobenzo[e]-1,2,5(2H)-oxaphosphorine, and the E and Z isomers of 2-(2,3,4,4,5-pentachlorocyclohexadienon-6-yl)-2-phenylvinylphosphonic dichloride. The molecular and supramolecular structure of the heterocycle and phosphorus-containing products of its hydrolysis were studied by single crystal X-ray diffraction.
• ——
  作者：V. F. Mironov、T. A. Baronova、A. I. Konovalov、N. M. Aznacheev、F. F. Alekseev、T. A. Zyablikova、R. Z. Musin

  DOI：10.1023/a:1020909828276

  日期：——

  Reaction in a three-component system tetrachloro-o-benzoquinone-arylacetylene-phosphorus trichloride was investigated with the use of NMR and IR spectroscopy and high resolution mass spectrometry. It was established that prevailingly formed 4-aryl-2-oxo-2,5,6,7,8-pentachlorobenzo[e]-1,2-oxaphosphorin-3-enes which on hydrolysis furnished 2-aryl-2-(1-hydroxy-2,3,4,5-tetrachlorophenyl)vinylphosphonic acids.