3-(4-hydroxy-3-methoxyphenyl)-3-(3,4-dichlorophenylamino)-2-(2-methoxyphenoxy)propan-1-ol | 208114-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-hydroxy-3-methoxyphenyl)-3-(3,4-dichlorophenylamino)-2-(2-methoxyphenoxy)propan-1-ol
• 英文别名: 4-[1-(3,4-Dichloroanilino)-3-hydroxy-2-(2-methoxyphenoxy)propyl]-2-methoxyphenol
• CAS: 208114-85-6
• 化学式: C₂₃H₂₃Cl₂NO₅
• 分子量: 464.345
• InChiKey: NPUIFXNZYZMAKK-UHFFFAOYSA-N

物化性质

• 沸点：
  670.6±55.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-3-methoxyphenyl)-3-(3,4-dichlorophenylamino)-2-(2-methoxyphenoxy)propan-1-ol 在 盐酸 作用下， 生成 3,4-二氯苯胺 、 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol
  参考文献：
  名称：

  Chloroaniline/Lignin Conjugates as Model System for Nonextractable Pesticide Residues in Crop Plants

  摘要：

  In vitro lignins formed by the peroxidase/H2O2-mediated polymerization of coniferyl alcohol in the presence of 3,4-dichloroaniline or [N-15]aniline were studied by H-1, C-13 and N-15 NMR spectroscopy. The anilines were >95% bound to the benzylic a-position of lignin side chains. Mild acid hydrolysis under simulated stomach conditions (0.1 M HCl, 37 degrees C) was studied as a first estimate of animal bioavailability. The two extremes,of facile or slow acid hydrolysis that are known for chloroaniline/lignin-comelexes could be reproduced by using low or high incorporation ratios of aniline to coniferyl alcohol (10 or 40 mol %, respectively). The case of facile a cid hydrolysis and high animal bioavailability may be due to the high; mole ratios used and may not be relevant for pesticidal crop plant residue levels of 3,4-dichloroaniline. The latter are typically in the parts per million range. On the basis of N-15 NMR spectre I fine structure; we propose that the acid-labile linkage may be due to anchimeric assistance in conformers formed at the high aniline molar ratio. The;optimized methods represented here allow the use; of in vitro lignin copolymers as a reference system for the structural features. and the bioavailability of nonextractable pesticide residues in crop plants.

  DOI：

  10.1021/es9801588
• 作为产物：
  描述：

  1-(4-(benzyloxy)-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one 在 sodium tetrahydroborate 、 三甲基溴硅烷 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 1.07h， 生成 3-(4-hydroxy-3-methoxyphenyl)-3-(3,4-dichlorophenylamino)-2-(2-methoxyphenoxy)propan-1-ol
  参考文献：
  名称：

  The Incorporation of 3,4-Dichloroaniline, a Pesticide Metabolite, into Dehydrogenation Polymers of Coniferyl Alcohol (DHPs).

  摘要：

  A mechanism by which pesticide metabolites may become incorporated into plant lignins has been studied with the aid of 3,4-dichloroaniline (DCA) and lignin model compounds. DCA was found to react rapidly with a quinone methide representing an intermediate in lignin biosynthesis. The resulting benzyl-amine group was stable to mild acidolysis under simulated stomach conditions. Addition of DCA to dehydrogenative polymerizations of coniferyl alcohol yielded DHPs containing covalently bended DCA. NMR spectroscopy showed that the DCA had become bonded to the benzylic position in arylglycerol-beta-guaiacyl ether structures. The majority of these structures were phenolic. This observation and the fact that the DCA accumulates in the low molecular weight fraction of the DHP indicates that the DCA functions as a trap for quinone methides and stops the further growth of the polymer.

  DOI：

  10.3891/acta.chem.scand.52-1338