3-(tert-butyldimethylsilyloxy)-5-chloro-4-hydroxybenzaldehyde | 1365030-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(tert-butyldimethylsilyloxy)-5-chloro-4-hydroxybenzaldehyde
• CAS: 1365030-65-4
• 化学式: C₁₃H₁₉ClO₃Si
• 分子量: 286.831
• InChiKey: FMDLWSHOOQBOHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsilyloxy)-5-chloro-4-hydroxybenzaldehyde 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 1,8-双二甲氨基萘 、 potassium carbonate 、 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-5-(tert-butyldimethylsilyloxy)-3-chloro-4-methoxyphenol
  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：

  3-氯-4,5-二羟基苯甲醛 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以70%的产率得到3-(tert-butyldimethylsilyloxy)-5-chloro-4-hydroxybenzaldehyde
  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