[(E)-(2-methyl-4-oxo-5-propan-2-ylcyclohexa-2,5-dien-1-ylidene)amino] 3-nitrobenzenesulfonate | 359827-55-7

• 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)-(2-methyl-4-oxo-5-propan-2-ylcyclohexa-2,5-dien-1-ylidene)amino] 3-nitrobenzenesulfonate
• CAS: 359827-55-7
• 化学式: C₁₆H₁₆N₂O₆S
• 分子量: 364.379
• InChiKey: KGGCCVZRUGOLQA-BMRADRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(E)-(2-methyl-4-oxo-5-propan-2-ylcyclohexa-2,5-dien-1-ylidene)amino] 3-nitrobenzenesulfonate 在 氯 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 以48%的产率得到[(E)-(5,6-dichloro-6-methyl-4-oxo-3-propan-2-ylcyclohex-2-en-1-ylidene)amino] 3-nitrobenzenesulfonate
  参考文献：
  名称：

  摘要：

  The chlorination and bromination of 2,3-dimethyl-, 3-methyl-6-isopropyl-, and 2,6-diisopropyl-4-aroyl(or arylsulfonyl)oxyimino-2,5-cyclohexadienones follow the proposed rules of halogenation of 4-aroyl-(or arylsulfonyl)oxyimino-2,5-cyclohexadienones: the reaction occurs preferentially at the cis-C=C bond of the quinoid ring; simultaneous halogenation at both double bonds is not observed; halogen adds mainly across unsubstituted C=C bond; no halogenation occurs at the double bond already substituted by a halogen; bromination of the C=C bond with an alkyl substituent is more difficult than chlorination; the second halogen molecule adds only after regioselective dehydrohalogenation.

  DOI：

  10.1023/a:1012403708255
• 作为产物：
  描述：

  (4E)-4-(Hydroxyimino)-2-isopropyl-5-methyl-2,5-cyclohexadien-1-on e 、 3-硝基苯磺酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 以93%的产率得到[(E)-(2-methyl-4-oxo-5-propan-2-ylcyclohexa-2,5-dien-1-ylidene)amino] 3-nitrobenzenesulfonate
  参考文献：
  名称：

  摘要：

  The chlorination and bromination of 2,3-dimethyl-, 3-methyl-6-isopropyl-, and 2,6-diisopropyl-4-aroyl(or arylsulfonyl)oxyimino-2,5-cyclohexadienones follow the proposed rules of halogenation of 4-aroyl-(or arylsulfonyl)oxyimino-2,5-cyclohexadienones: the reaction occurs preferentially at the cis-C=C bond of the quinoid ring; simultaneous halogenation at both double bonds is not observed; halogen adds mainly across unsubstituted C=C bond; no halogenation occurs at the double bond already substituted by a halogen; bromination of the C=C bond with an alkyl substituent is more difficult than chlorination; the second halogen molecule adds only after regioselective dehydrohalogenation.

  DOI：

  10.1023/a:1012403708255

文献信息

• ——
  作者：A. P. Avdeenko、S. V. Shishkina、O. V. Shishkin、N. M. Glinyanaya、S. A. Konovalova、S. A. Goncharova

  DOI：10.1023/a:1019611105962

  日期：——
• 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.