[(E)-(5,6-dibromo-3-methyl-4-oxocyclohex-2-en-1-ylidene)amino] benzenesulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(E)-(5,6-dibromo-3-methyl-4-oxocyclohex-2-en-1-ylidene)amino] benzenesulfonate
• 化学式: C₁₃H₁₁Br₂NO₄S
• 分子量: 437.109
• InChiKey: POLAKVFVXVFQBW-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(E)-(5,6-dibromo-3-methyl-4-oxocyclohex-2-en-1-ylidene)amino] benzenesulfonate 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 [(Z)-(3-bromo-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino] benzenesulfonate 、 [(E)-(3-bromo-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino] benzenesulfonate
  参考文献：
  名称：

  摘要：

  Halogenation of 4-aroyl (arylsulfonyl)oxyimino-2-methyl-2,5-cyclohexadienones yields ZE-isomeric 4-aroyl(arylsulfonyl)oxyimino-5,6-dihalo-2-methyl-2-cyclohexenones and (E)-4-aroyl(arylsulfonyl)oxyimino-5,6-dihalo-6-methyl-2-cyclohexenones. Further chlorination leads to formation of (Z,E)-4-aroyl(arylsulfonyl)oxyimino-2,5,6-trichloro-6-methyl-2-cyclohexenones.

  DOI：

  10.1023/a:1019663122800
• 作为产物：
  描述：

  methyl-[1,4]benzoquinone-4-(O-benzenesulfonyl oxime ) 在 溴 作用下， 以 氯仿 为溶剂， 生成 、 [(E)-(5,6-dibromo-3-methyl-4-oxocyclohex-2-en-1-ylidene)amino] benzenesulfonate
  参考文献：
  名称：

  Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: III. Regioselectivity in the halogenation of N-aroyl(arylsulfonyl)oxyimino-2,5-cyclohexadienones

  摘要：

  Halogenation of 4-aroyl(arylsulfonyl)oxyimino-2,5-cyclohexadienones is not accompanied by change of the configuration at the nitrogen atom. p-Benzoquinone oxime ethers and esters take up halogens in a regioselective fashion at the syn-C=C bond of the quinoid ring. The main factor responsible for regioselective addition of halogens is configuration at the nitrogen atom, which determines the stability of intermediate halogenonium ion.

  DOI：

  10.1134/s1070428006010106

文献信息

• ——
  作者：A. P. Avdeenko、N. M. Glinyanaya、S. A. Konovalova、S. A. Goncharova

  DOI：10.1023/a:1019663122800

  日期：——

  Halogenation of 4-aroyl (arylsulfonyl)oxyimino-2-methyl-2,5-cyclohexadienones yields ZE-isomeric 4-aroyl(arylsulfonyl)oxyimino-5,6-dihalo-2-methyl-2-cyclohexenones and (E)-4-aroyl(arylsulfonyl)oxyimino-5,6-dihalo-6-methyl-2-cyclohexenones. Further chlorination leads to formation of (Z,E)-4-aroyl(arylsulfonyl)oxyimino-2,5,6-trichloro-6-methyl-2-cyclohexenones.
• Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: III. Regioselectivity in the halogenation of N-aroyl(arylsulfonyl)oxyimino-2,5-cyclohexadienones
  作者：A. P. Avdeenko、S. A. Konovalova、A. Ya. Il’chenko、N. M. Glinyanaya

  DOI：10.1134/s1070428006010106

  日期：2006.1

  Halogenation of 4-aroyl(arylsulfonyl)oxyimino-2,5-cyclohexadienones is not accompanied by change of the configuration at the nitrogen atom. p-Benzoquinone oxime ethers and esters take up halogens in a regioselective fashion at the syn-C=C bond of the quinoid ring. The main factor responsible for regioselective addition of halogens is configuration at the nitrogen atom, which determines the stability of intermediate halogenonium ion.