2-bromo-3-chloro-5-methoxy-1,4-benzoquinone | 1365030-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3-chloro-5-methoxy-1,4-benzoquinone
• 英文别名: 2-Bromo-3-chloro-5-methoxycyclohexa-2,5-diene-1,4-dione；2-bromo-3-chloro-5-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 1365030-56-3
• 化学式: C₇H₄BrClO₃
• 分子量: 251.464
• InChiKey: DPEHSFUJVFBUJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-3-chloro-5-methoxy-1,4-benzoquinone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 0.25h， 以98%的产率得到2-bromo-3-chloro-5-methoxy-1,4-dihydroxybenzene
  参考文献：
  名称：

  Redox potentials, laccase oxidation, and antilarval activities of substituted phenols

  摘要：

  Laccases are copper-containing oxidases that are involved in sclerotization of the cuticle of mosquitoes and other insects. Oxidation of exogenous compounds by insect laccases may have the potential to produce reactive species toxic to insects. We investigated two classes of substituted phenolic compounds, halogenated di- and trihydroxybenzenes and substituted di-tert-butylphenols, on redox potential, oxidation by laccase and effects on mosquito larval growth. An inverse correlation between the oxidation potentials and laccase activity of halogenated hydroxybenzenes was found. Substituted di-tert-butylphenols however were found to impact mosquito larval growth and survival. In particular, 2,4-di-tert-butyl-6-(3-methyl-2-butenyl)phenol (15) caused greater than 98% mortality of Anopheles gambiae larvae in a concentration of 180 nM, whereas 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropanal oxime (13) and 6,8-di-tert-butyl-2,2-dimethyl-3,4-dihydro-2H-chromene (33) caused 93% and 92% mortalities in concentrations of 3.4 and 3.7 mu M, respectively. Larvae treated with di-tert-butylphenolic compounds died just before pupation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.021
• 作为产物：
  描述：

  5-氯香草醛 在 甲醇 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 2-bromo-3-chloro-5-methoxy-1,4-benzoquinone
  参考文献：
  名称：

  Redox potentials, laccase oxidation, and antilarval activities of substituted phenols

  摘要：

  Laccases are copper-containing oxidases that are involved in sclerotization of the cuticle of mosquitoes and other insects. Oxidation of exogenous compounds by insect laccases may have the potential to produce reactive species toxic to insects. We investigated two classes of substituted phenolic compounds, halogenated di- and trihydroxybenzenes and substituted di-tert-butylphenols, on redox potential, oxidation by laccase and effects on mosquito larval growth. An inverse correlation between the oxidation potentials and laccase activity of halogenated hydroxybenzenes was found. Substituted di-tert-butylphenols however were found to impact mosquito larval growth and survival. In particular, 2,4-di-tert-butyl-6-(3-methyl-2-butenyl)phenol (15) caused greater than 98% mortality of Anopheles gambiae larvae in a concentration of 180 nM, whereas 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropanal oxime (13) and 6,8-di-tert-butyl-2,2-dimethyl-3,4-dihydro-2H-chromene (33) caused 93% and 92% mortalities in concentrations of 3.4 and 3.7 mu M, respectively. Larvae treated with di-tert-butylphenolic compounds died just before pupation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.021

文献信息

• Redox potentials, laccase oxidation, and antilarval activities of substituted phenols
  作者：Keshar Prasain、Thi D.T. Nguyen、Maureen J. Gorman、Lydia M. Barrigan、Zeyu Peng、Michael R. Kanost、Lateef U. Syed、Jun Li、Kun Yan Zhu、Duy H. Hua

  DOI：10.1016/j.bmc.2012.01.021

  日期：2012.3

  Laccases are copper-containing oxidases that are involved in sclerotization of the cuticle of mosquitoes and other insects. Oxidation of exogenous compounds by insect laccases may have the potential to produce reactive species toxic to insects. We investigated two classes of substituted phenolic compounds, halogenated di- and trihydroxybenzenes and substituted di-tert-butylphenols, on redox potential, oxidation by laccase and effects on mosquito larval growth. An inverse correlation between the oxidation potentials and laccase activity of halogenated hydroxybenzenes was found. Substituted di-tert-butylphenols however were found to impact mosquito larval growth and survival. In particular, 2,4-di-tert-butyl-6-(3-methyl-2-butenyl)phenol (15) caused greater than 98% mortality of Anopheles gambiae larvae in a concentration of 180 nM, whereas 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropanal oxime (13) and 6,8-di-tert-butyl-2,2-dimethyl-3,4-dihydro-2H-chromene (33) caused 93% and 92% mortalities in concentrations of 3.4 and 3.7 mu M, respectively. Larvae treated with di-tert-butylphenolic compounds died just before pupation. (C) 2012 Elsevier Ltd. All rights reserved.