3-methyl-N-(4-chlorobenzoyl)-1,4-benzoquinone monoimine | 1266605-51-9

• 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: 3-methyl-N-(4-chlorobenzoyl)-1,4-benzoquinone monoimine
• CAS: 1266605-51-9
• 化学式: C₁₄H₁₀ClNO₂
• 分子量: 259.692
• InChiKey: ZGBVLVDBRCGFNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-methyl-N-(4-chlorobenzoyl)-1,4-benzoquinone monoimine 在 氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-methyl-4-(4-chlorobenzoyl)imino-2,3,5,6,6-pentachlorocyclohex-2-en-1-one
  参考文献：
  名称：

  Halogenation of N-substituted p-quinone monoimines and p-quinonemonooxime ethers: XII. Halogenation of N-aroyl-2(3)-methyl-1,4-benzoquinone monoimines and their reduced forms

  摘要：

  A strong acceptor substituent at the nitrogen atom of the N-substituted p-quinone monoimine decreases the stability of the halogen-containing cyclohexene structures formed at the addition of a halogen molecule to the C=C bond of the quinoid ring. As a result of the bromination of N-benzoyl-2-methyl-1,4-benzoquinone monoimine alongside the usual products of addition and substitution the 5-benzoyloxy-2,3,6-tribromo-6-methylcyclohex-2ene-1,4-dione was isolated.

  DOI：

  10.1134/s1070428010110035
• 作为产物：
  描述：

  对氯苯甲酸 在 sodium acetate 、 lead(IV) tetraacetate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-methyl-N-(4-chlorobenzoyl)-1,4-benzoquinone monoimine
  参考文献：
  名称：

  Halogenation of N-substituted p-quinone monoimines and p-quinonemonooxime ethers: XII. Halogenation of N-aroyl-2(3)-methyl-1,4-benzoquinone monoimines and their reduced forms

  摘要：

  A strong acceptor substituent at the nitrogen atom of the N-substituted p-quinone monoimine decreases the stability of the halogen-containing cyclohexene structures formed at the addition of a halogen molecule to the C=C bond of the quinoid ring. As a result of the bromination of N-benzoyl-2-methyl-1,4-benzoquinone monoimine alongside the usual products of addition and substitution the 5-benzoyloxy-2,3,6-tribromo-6-methylcyclohex-2ene-1,4-dione was isolated.

  DOI：

  10.1134/s1070428010110035

文献信息

• Reaction of some N-substituted 1,4-benzoquinone imines with sodium arenesulfinates
  作者：S. A. Konovalova、A. P. Avdeenko、I. L. Marchenko

  DOI：10.1134/s1070428014070082

  日期：2014.7

  N-Arylsulfonyl, N-aroyl, and N-[arylsulfonylimino(phenyl)methyl] derivatives of 1,4-benzoquinone imine reacted with sodium arenesulfinates to give 1,4-, 1,6-, and 6,1-addition products which were formed according to two concurrent paths: direct nucleophilic addition of arenesulfinate anion to neutral quinone imine molecule and radical ion addition of arenesulfinate radical to radical anion derived

  Ñ -Arylsulfonyl，Ñ芳酰基，和Ñ - [arylsulfonylimino（苯基）甲基] -1,4-苯醌亚胺衍生物与钠arenesulfinates反应，得到1,4-，1,6-，和6,1加成产物，其根据两个并发路径形成：将芳族亚磺酸根阴离子直接亲核加成到中性醌亚胺分子上，以及将芳族亚磺酸根自由基加成至醌基亚胺衍生的自由基上的自由基离子。
• Hydrohalogenation of N-acetyl(aroyl)-1,4-benzoquinone monoimines
  作者：A. P. Avdeenko、S. A. Konovalova、O. N. Ludchenko、O. P. Ledeneva、A. V. Vakulenko

  DOI：10.1134/s1070428011020102

  日期：2011.2

  New N-acetyl-1,4-benzoquinone monoimines alkyl-substituted in the quinoid ring were synthesized. The hydrohalogenation of N-acetyl(aroyl)-1,4-benzoquinone monoimines proceeds exclusively in keeping with the 1,4-addition. The hydrochlorination occurs along the ionic mechanism, in the hydrobromination grows the role of the radical mechanism.