2,2,4,4,6-pentachloro-5-cyclohexen-1,3-dione | 15679-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,4,4,6-pentachloro-5-cyclohexen-1,3-dione
• 英文别名: Pentachlorresorcin; 2.2.4.6.6-Pentachlor-cyclohexen-(4)-dion-(1.3)；2,2,4,6,6-pentachloro-cyclohex-4-ene-1,3-dione；2,2,4,6,6-Pentachlor-cyclohex-4-en-1,3-dion；Pentachlorresorcin；2,2,4,4,6-Pentachloro-5-cyclohexene-1,3-dione；2,2,4,6,6-pentachlorocyclohex-4-ene-1,3-dione
• CAS: 15679-05-7
• 化学式: C₆HCl₅O₂
• 分子量: 282.338
• InChiKey: NTFAWJMNLRUDJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,4,4,6-pentachloro-5-cyclohexen-1,3-dione 在 calcium chloride 作用下， 生成 3,5,5,5-tetrachloro-4-oxo-pent-2-enoic acid
  参考文献：
  名称：

  Zincke; Fuchs, Chemische Berichte, 1893, vol. 26, p. 508

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯间苯二酚 在 氯胺 作用下， 以 乙醚 为溶剂， 生成 2,2,4,4,6-pentachloro-5-cyclohexen-1,3-dione
  参考文献：
  名称：

  Reactions of resorcinol and its chlorinated derivatives with monochloramine: Identification of intermediates and products

  摘要：

  AbstractAn investigation of the reaction of resorcinol (compound 1) and its chlorinated derivatives 4‐chlororesorcinol (compound 4), 4,6‐dichlororesorcinol (compound 5), and 2,4,6‐trichlororesorcinol (compound 2) with monochloramine (NH2Cl) in ether and aqueous solution (pH 7) is reported. NH2Cl reacted with compounds 1, 2, 4, and 5 to give the pentachloro intermediate, 2,2,4,4,6‐pentachloro‐5‐cyclohexen‐1,3‐dione (compound 3), which underwent ring opening with H2O and loss of CO2 in the presence of NH2Cl to produce the following: 1,1,3,5,5‐pentachloro‐3‐penten‐2‐one (compound 6), 1,1,1,3,5,5‐hexachloro‐3‐penten‐2‐one (compound 7), and 1,1,3,5,5,5‐hexachloro‐3‐penten‐2‐one (compound 8). Compound 6 reacted further with NH2Cl to give compounds 7 and 8; in the presence of NH2Cl, compound 7 rearranged to compound 8. Mechanisms for the preceding reactions are analyzed in detail. Another aspect of the investigation involved a determination of the amounts of chloroform, CHCl3, which is produced from compound 3 with NH2Cl (4%) and with NaOCl (50%). The low production of CHCl3 from compound 3 and NH2Cl is discussed in connection with the probable reactions of compounds 7 and 8 with NH2Cl and H2O.

  DOI：

  10.1002/etc.5620181104

文献信息

• Zincke, Chemische Berichte, 1890, vol. 23, p. 3779
  作者：Zincke

  DOI：——

  日期：——
• Zincke, Chemische Berichte, 1890, vol. 23, p. 3781
  作者：Zincke

  DOI：——

  日期：——
• v. d. Stelt et al., Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 1022,1026
  作者：v. d. Stelt et al.

  DOI：——

  日期：——
• Claassen, Chemische Berichte, 1878, vol. 11, p. 1440
  作者：Claassen

  DOI：——

  日期：——
• Zincke; Rabinowitsch, Chemische Berichte, 1890, vol. 23, p. 3777
  作者：Zincke、Rabinowitsch

  DOI：——

  日期：——

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