2,3,5,6-tetrachloro-4-(phenylimino)-cyclohexa-2,5-dien-1-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,3,5,6-tetrachloro-4-(phenylimino)-cyclohexa-2,5-dien-1-one
• 英文别名: 2,3,5,6-Tetrachloro-4-phenyliminocyclohexa-2,5-dien-1-one
• 化学式: C₁₂H₅Cl₄NO
• 分子量: 320.99
• InChiKey: SXEMJWVJBIISTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氯苯醌 、 四苯基氨化膦 以 四氢呋喃 为溶剂， 以80%的产率得到2,3,5,6-tetrachloro-4-(phenylimino)-cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  THE BEHAVIOR OFN-PHENYLIMINOPHOSPHORANE TOWARDSo- ANDp-QUINONES. NEW SYNTHESIS OF DIOXAZOLE AND OXADIAZOLE DERIVATIVES

  摘要：

  N-Phenyliminophosphorane (1) reacts with 9,10-phenanthrenequinone (2a) to give the new products 2-phenylphenanthro[9,10-d][1,3,2]dioxazole (4a) and (10Z)-10-(phenylimino)-9(10H) phenanthrenone (4b). The reaction of I with 1,2-naphthoquinone (2b) afforded both the dioxazole derivative 5a and the known 2-anilino-naphthoquinone-1,4-anil (5b). On the other hand, 2,6-di-tert-butyl-2,3-diphenyl-2,3-dihydro-1,2,3-benzoxadiazole (6) was obtained from the reaction of (2c) with phosphinimine (1). Application of reagent 1 on 2d and 2e renders (6E)-2,3,4,5-tetrahalogeno-6-(phenylimino)-2,4-cyclohexadien-1-one 7a and 7b, respectively. Moreover, p-quinones (3a-3c) react with phosphinimine (1) to yield products 8, 9 and 10, respectively. Mechanisms accounting for the formation of the new products are discussed and the probable structures of the products are presented based on analytical and spectroscopic data.

  DOI：

  10.1081/scc-120006460

文献信息

• Quinone imine dye formation via photocycloaddition between isocyanates and chloranil
  作者：Kan Wakamatsu

  DOI：10.1016/j.tetlet.2004.04.107

  日期：2004.6

  Photochemical [2+2]cycloaddition between electron-donating aryl isocyanates and chloranil was observed in acetonitrile or benzene, and the following elimination of carbon dioxide resulted in the formation of the corresponding quinone imine dyes. This new route for synthesis of quinone imine was investigated by product analyses, laser flash photolyses, and molecular orbital calculation.

  在乙腈或苯中观察到给电子的芳基异氰酸酯与氯腈之间的光化学[2 + 2]环加成反应，随后消除二氧化碳导致形成相应的醌亚胺染料。通过产物分析，激光闪光光解和分子轨道计算研究了这种合成醌亚胺的新途径。
• THE BEHAVIOR OF<i>N</i>-PHENYLIMINOPHOSPHORANE TOWARDS<i>o</i>- AND<i>p</i>-QUINONES. NEW SYNTHESIS OF DIOXAZOLE AND OXADIAZOLE DERIVATIVES
  作者：Leila S. Boulos、Mona H. N. Arsanious

  DOI：10.1081/scc-120006460

  日期：2002.1

  N-Phenyliminophosphorane (1) reacts with 9,10-phenanthrenequinone (2a) to give the new products 2-phenylphenanthro[9,10-d][1,3,2]dioxazole (4a) and (10Z)-10-(phenylimino)-9(10H) phenanthrenone (4b). The reaction of I with 1,2-naphthoquinone (2b) afforded both the dioxazole derivative 5a and the known 2-anilino-naphthoquinone-1,4-anil (5b). On the other hand, 2,6-di-tert-butyl-2,3-diphenyl-2,3-dihydro-1,2,3-benzoxadiazole (6) was obtained from the reaction of (2c) with phosphinimine (1). Application of reagent 1 on 2d and 2e renders (6E)-2,3,4,5-tetrahalogeno-6-(phenylimino)-2,4-cyclohexadien-1-one 7a and 7b, respectively. Moreover, p-quinones (3a-3c) react with phosphinimine (1) to yield products 8, 9 and 10, respectively. Mechanisms accounting for the formation of the new products are discussed and the probable structures of the products are presented based on analytical and spectroscopic data.