2,8-dichloro-4-chloromethyl-2H-benzo[e][1,2,λ⁵]oxaphosphorine 2-oxide | 294198-70-2

• 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: 2,8-dichloro-4-chloromethyl-2H-benzo[e][1,2,λ⁵]oxaphosphorine 2-oxide
• 英文别名: 2,8-dichloro-4-(chloromethyl)-2H-1,2λ⁵-benzoxaphosphinin-2-one；2,8-Dichloro-4-(chloromethyl)-1,2lambda5-benzoxaphosphinine 2-oxide；2,8-dichloro-4-(chloromethyl)-1,2λ5-benzoxaphosphinine 2-oxide
• CAS: 294198-70-2
• 化学式: C₉H₆Cl₃O₂P
• 分子量: 283.478
• InChiKey: KDBGAFLCTMUZCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2,8-dichloro-4-chloromethyl-2H-benzo[e][1,2,λ⁵]oxaphosphorine 2-oxide 在 水 作用下， 以 乙醚 、 丙酮 为溶剂， 以95%的产率得到8-chloro-4-(chloromethyl)-2-hydroxy-2H-1,2λ⁵-benzoxaphosphinin-2-one
  参考文献：
  名称：

  Reaction of trihalo(phenylenedioxy)phosphoranes with acetylenes: X. specific features of the reactions of substituted 2,2,2-trichloro-1,3,2λ5-benzodioxaphospholes with 3-chloro(bromo, iodo)propynes

  摘要：

  It was shown for the first time that 3-chloro-, 3-bromo-, and 3-iodopropynes can react with 2.2.2-trichloro-. 2.2.2-trichloro-5-methyl-, and 5,6-dibromo-2,2,2-tricliloro-1,3,2 lambda(5)-benzodioxaphosplioles to Live derivatives of 4-(haloniethyl)-2-chloro-2H-1,2 lambda(5)-benzoxaphosphinin-2-ones. The reaction involves nonselective chlorination of the phenylene substituent in different positions, and the resulting isomer ratio is temperature-dependent. In the reactions of 3-bromo- and 3-iodopropynes with 2,2,2-trichloro-1,3,2 lambda(5)-belizodioxaphosphole. a side process takes place, viz. nucleophilic substitution of bromine and iodine with chlorine. The structure of some of the prepared 4-(chloromethyl)-1,2- benzoxaphosphi nines was studied by means of X-ray diftraction.

  DOI：

  10.1134/s1070363206030091
• 作为产物：
  描述：

  3-氯丙炔 、 1,2-亚苯基三氯磷酸 生成 2,8-dichloro-4-chloromethyl-2H-benzo[e][1,2,λ⁵]oxaphosphorine 2-oxide
  参考文献：
  名称：

  亚芳基二氧基三卤代正膦与烷基和芳基乙炔反应的新数据

  摘要：

  总结了有关取代的亚芳基二氧基三卤代正膦与单烷基或芳基乙炔之间反应的新数据。该反应导致形成六元杂环-2-oxo-4-R-benzo[e]-1,2-oxaphosphorin-3-enes。讨论了正膦和乙炔分子中的取代基对本位取代和卤化区域化学的影响。已经观察到氯上叔丁基的同位取代和氯上溴和氢上碘的交换，以及苯并膦的形成。四氯邻苯醌与三氯化磷和芳基乙炔的相互作用被提议作为导致形成苯并[e]-1,2-氧杂磷的反应的新改进。一些苯并[e]-1的结构，

  DOI：

  10.1080/10426500212243

文献信息

• The New Data for the Reaction of Arylenedioxy Trihalogenophosphoranes with Alkyl- and Arylacetylenes
  作者：Vladimir F. Mironov、Alfiya A. Shtyrlina、Ravil R. Petrov、Tamara A. Baronova、Fedor F. Alekseev、Elena N. Varaksina、Aleksander I. Konovalov

  DOI：10.1080/10426500212243

  日期：2002.6.1

  halogenation regiochemistry are discussed. The ipso -substitution of tert -butyl group on chlorine and the exchange of bromine on chlorine and iodine on hydrogen have been observed, along with formation of benzophosphorines. The interaction of tetrachloro- ortho -benzoquinone with phosphorus trichloride and arylacetylenes is proposed as a new modification of the reaction leading to the formation of benzo[ e ]-1

  总结了有关取代的亚芳基二氧基三卤代正膦与单烷基或芳基乙炔之间反应的新数据。该反应导致形成六元杂环-2-oxo-4-R-benzo[e]-1,2-oxaphosphorin-3-enes。讨论了正膦和乙炔分子中的取代基对本位取代和卤化区域化学的影响。已经观察到氯上叔丁基的同位取代和氯上溴和氢上碘的交换，以及苯并膦的形成。四氯邻苯醌与三氯化磷和芳基乙炔的相互作用被提议作为导致形成苯并[e]-1,2-氧杂磷的反应的新改进。一些苯并[e]-1的结构，
• Mironov; Shtyrlina; Azancheev, Russian Journal of General Chemistry, 2000, vol. 70, # 1, p. 152 - 153
  作者：Mironov、Shtyrlina、Azancheev、Konovalov

  DOI：——

  日期：——
• Reaction of trihalo(phenylenedioxy)phosphoranes with acetylenes: X. specific features of the reactions of substituted 2,2,2-trichloro-1,3,2λ5-benzodioxaphospholes with 3-chloro(bromo, iodo)propynes
  作者：V. F. Mironov、E. N. Varaksina、A. A. Shtyrlina、A. T. Gubaidullin、N. M. Azancheev、R. S. Musin、I. A. Litvinov、A. I. Konovalov

  DOI：10.1134/s1070363206030091

  日期：2006.3

  It was shown for the first time that 3-chloro-, 3-bromo-, and 3-iodopropynes can react with 2.2.2-trichloro-. 2.2.2-trichloro-5-methyl-, and 5,6-dibromo-2,2,2-tricliloro-1,3,2 lambda(5)-benzodioxaphosplioles to Live derivatives of 4-(haloniethyl)-2-chloro-2H-1,2 lambda(5)-benzoxaphosphinin-2-ones. The reaction involves nonselective chlorination of the phenylene substituent in different positions, and the resulting isomer ratio is temperature-dependent. In the reactions of 3-bromo- and 3-iodopropynes with 2,2,2-trichloro-1,3,2 lambda(5)-belizodioxaphosphole. a side process takes place, viz. nucleophilic substitution of bromine and iodine with chlorine. The structure of some of the prepared 4-(chloromethyl)-1,2- benzoxaphosphi nines was studied by means of X-ray diftraction.