3,5-Dimethyl-p-benzoquionone-4-imine | 132298-15-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,5-Dimethyl-p-benzoquionone-4-imine
• 英文别名: 3,5-dimethyl-p-benzoquinone imine；2,5-Cyclohexadien-1-one, 3,5-dimethyl-4-imino-；4-imino-3,5-dimethylcyclohexa-2,5-dien-1-one
• CAS: 132298-15-8
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: UHVVLGDTSBKXLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二甲基-4-氨基苯酚 在 lead(IV) acetate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.17h， 生成 3,5-Dimethyl-p-benzoquionone-4-imine
  参考文献：
  名称：

  Dialkylquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes

  摘要：

  Some of the most widely-used herbicides are the chloroacetanilides exemplified by alachlor and butachlor (derived from 2,6-diethylaniline) and metolachlor and acetochlor (synthesized from 2-ethyl-6-methyIaniline). This investigation tests the hypothesis that the previously-observed oncogenicity of these herbicides is due to genotoxic intermediates such as diethylbenzoquinoneimine, a purported alachlor metabolite. Syntheses are reported here for the corresponding 2,6-dialkylbenzoquinoneimines, selected chloroacetyldialkylbenzoquinoneimines and several other candidate or known metabolites. The possible mutagenicity of diethylbenzoquinoneimine was tested in Salmonella typhimurium strains TA98 and TA100 with a weakly-positive response in the TA100 strain indicating induction of base-pair substitution mutations. The frequency of sister chromatid exchange (SCE) in Chinese hamster ovary cells was increased by alachlor at 10 mu M and diethylaniline but not ethylmethylaniline at 30 and 3 mu M Isolated and cultured peripheral lymphocytes (mostly T cells) were used from two human donors to study the effects of the chloroacetanilides and their metabolites on primary human cells. In tests at 10 mu M, the SCE frequency was increased by alachlor and possibly acetochlor but not by butachlor, metolachlor, dimethachlor (a 2,6-dimethyl analog) and dimethenamid (an analog based on 2,4-dimethyl-3 -thienylamine). At 0.3 mu M in cultured human lymphocytes, alachlor, the corresponding chloroacetanilide( N-dealkyl-alachlor) and aniline metabolites (and their 4-hydroxy derivatives), and diethylbenzoquinone were inactive or active in only one of the two donors whereas at 0.1-0.3 mu M the SCE ratio for treated cells divided by the controls was always higher for diethylbenzoquinoneimine than for ethylmethyl- and dimethylbenzoquinoneimines. All the tested compounds were toxic to lymphocytes, but the depression of the mitotic index and increased duration of the cell cycle were not directly linked with SCE induction. Previous investigations have suggested that chloroacetanilide herbicides such as alachlor derived from 2,6-dialkylanilines are metabolized to 2,6-dialkylbenzoquinoneimines and the present study provides the first direct evidence that these metabolites are genotoxic in human lymphocytes. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s1383-5718(97)00163-0

文献信息

• Grampp, Guenter, Journal of the Chemical Society. Perkin transactions II, 1984, p. 2001 - 2004
  作者：Grampp, Guenter

  DOI：——

  日期：——
• Steric effects on the pKa of N-protonated N-acetyl-p-benzoquinone imines: evidence for hydration via N-protonation
  作者：Michael Novak、Kristy Ann Martin

  DOI：10.1021/jo00004a045

  日期：1991.2

  The specific acid catalyzed hydration rate constant for N-acetyl-p-benzoquinone imine (1a) is (7.7 x 10(3))-fold larger than that of its 2,6-dimethyl analogue 1b. Since the uncatalyzed attack of small nucleophiles on C-1 of 1b is not significantly hindered, it had been proposed that pK(a)N (eq 1) for 1a must be ca. 3.2 units larger than that for 1b. Little evidence was available to distinguish between the hydration mechanisms of eqs 1 and 2. Measurements of pK(a)N for the deacylated iminium ions 5a and 5b and the results of ab initio calculations on the structures and energies of 1-5 indicate that N-protonation of 1a is favored over 1b by up to 5 orders of magnitude. A combination of steric hindrance to solvation of the acidic photon in 2b and sterically enforced destabilization of 2b appear to be the causes of this large DELTA-pK(a)N. These same calculations indicate that O-protontion of 1b is favored over that of 1a. This result provides support for the hydration mechanism of eq 1 since the O-protonation mechanism of eq 2 would predict more rapid hydration of 1b.
• US4007747A
  申请人：——

  公开号：US4007747A

  公开（公告）日：1977-02-15
• US4008043A
  申请人：——

  公开号：US4008043A

  公开（公告）日：1977-02-15
• US4008999A
  申请人：——

  公开号：US4008999A

  公开（公告）日：1977-02-22