2,6-Bis(1-methylethyl)-2,5-cyclohexadiene-1,4-dione 4-[O-[(4-methylphenyl)sulfonyl]oxime] | 55488-20-5

• 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: 2,6-Bis(1-methylethyl)-2,5-cyclohexadiene-1,4-dione 4-[O-[(4-methylphenyl)sulfonyl]oxime]
• 英文别名: [[4-oxo-3,5-di(propan-2-yl)cyclohexa-2,5-dien-1-ylidene]amino] 4-methylbenzenesulfonate
• CAS: 55488-20-5
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: PPJPJHFIERQDDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  2,6-Bis(1-methylethyl)-2,5-cyclohexadiene-1,4-dione 4-[O-[(4-methylphenyl)sulfonyl]oxime] 在 氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到
  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：

  2,6-bis(1-methylethoxy)phenol 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 以56%的产率得到2,6-Bis(1-methylethyl)-2,5-cyclohexadiene-1,4-dione 4-[O-[(4-methylphenyl)sulfonyl]oxime]
  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

• Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters: VII. Halogenation of 4-aroyl(arylsulfonyl)imino- and 4-aroyl(arylsulfonyl)-oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones
  作者：A. P. Avdeenko、V. V. Pirozhenko、O. V. Shishkin、S. V. Shishkina、S. A. Konovalova、O. N. Ludchenko

  DOI：10.1134/s1070428008040131

  日期：2008.4

  Halogenation of 4-aroyl(arylsulfonyl)imino-2,6-diisopropylcyclohexa-2,5-dien-1-ones gave 4-aroyl(arylsulfonyl)imino-3-halo-2,6-diisopropylcyclohexa-2,5-dien- -1-ones and 4-aroyl(arylsulfonyl)imino-3,5,6-trihalo-2,6-diisopropylcyclobex-2-en-1-ones. The latter were formed as mixtures of two stereoisomers, and the isopropyl group on the sp(3)-hybridized carbon atom in one stereoisomer occupies axial position, which is untypical of such compounds. Halogenation of 4-aroyl(arylsulfonyl)oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones leads to the formation of the corresponding addition products with traditional trans-diaxial arrangement of the halogen atoms.
• ——
  作者：A. P. Avdeenko、S. A. Zhukova、S. A. Konovalova

  DOI：10.1023/a:1012403708255

  日期：——

  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.