2-羟基-2,6-二乙基-N-甲氧基甲基乙酰苯胺 | 56681-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-2,6-二乙基-N-甲氧基甲基乙酰苯胺
• 中文别名: 2-羟基甲草胺
• 英文名称: 2-Hydroxy-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide
• 英文别名: N-hydroxymethylcarbonyl-N-methoxymethyl-2,6-diethylaniline；2-Hydroxy-2',6'-diethyl-N-(methoxymethyl)acetanilide；hydroxy-alachlor；hydroxyalachlor；2',6'-diethyl-N-(methoxymethyl)-2-hydroxyacetanilide；N-(2,6-diethylphenyl)-2-hydroxy-N-(methoxymethyl)acetamide
• CAS: 56681-55-1
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: CEFLNPUKMSWYFB-UHFFFAOYSA-N

物化性质

• 沸点：
  411.1±45.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-2,6-二乙基-N-甲氧基甲基乙酰苯胺 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 2-Oxo-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide
  参考文献：
  名称：

  Metabolites of Alachlor in Water:  Identification by Mass Spectrometry and Chemical Synthesis

  摘要：

  This biodegradation study of alachlor in water was designed to assess the presence and the identity of metabolites. Alachlor was incubated in river water for 28 days. The pesticide and its transformation products were extracted by solid phase extraction and analyzed by gas chromatography/mass spectrometry. Selected samples were also analyzed by liquid chromatography/mass spectrometry. The disappearance of the pesticide was not significative, but several compounds were identified as alachlor metabolites. Nine compounds were confirmed by comparison with synthetic standards. One metabolite has never been reported. For seven molecules, formulae were presumed on the basis of spectrum interpretation and literature data.

  DOI：

  10.1021/es970380x
• 作为产物：
  描述：

  N-acetoxyacetyl-2,6-diethylaniline 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 2-羟基-2,6-二乙基-N-甲氧基甲基乙酰苯胺
  参考文献：
  名称：

  Comparative photodegradation rates of alachlor and bentazone in natural water and determination of breakdown products

  摘要：

  AbstractThe photochemical degradation of the herbicides alachlor (2‐chloro‐2′,6′‐diethyl‐N‐methoxymethylacetanilide) and bentazone (3‐isopropyl‐(1H)‐2,1,3‐benzothiadiazin‐4(3H)‐one‐2,2‐dioxide) in distilled water and in river water, under xenon arc lamp irradiation, was investigated. Analytical determinations were carried out by using a xenon arc photoreactor and online solid‐phase extraction coupled to liquid‐chromatography diode‐array and liquid‐chromatography mass‐spectrometry detection systems. Photolysis experiments were performed at low concentration (20 μg/L), and the advantages of this methodology over conventional techniques are discussed. The photodegradation of alachlor and bentazone is a process depending on the water type, humic substances, and pH. When using a solution of 4 mg/L of humic matter, the estimated alachlor and bentazone half‐lives were 84 and 150 min, respectively, using a total irradiance of 550 W/m2 in the range of 300 to 800 nm. The degradation of alachlor and bentazone followed pseudo second‐ and first‐order kinetics, respectively. The major photodegradation products of both herbicides were identified either by on‐line solid‐phase extraction (SPE)‐liquid chromatography‐thermospray mass spectrometry (LC/TSP‐MS) or on‐line‐SPE‐LC/TSP‐tandem mass spectrometry (LC/TSP‐MS/MS). In addition to that, a total of six transformation products of alachlor were synthesized in our laboratory and their MS spectra were compared with those of the breakdown products obtained. After photodegradation, a total of 14 photoproducts resulted from alachlor dechlorination with subsequent hydroxylation and cyclization processes. The two major photoproducts were identified as hydroxy‐alachlor and 8‐ethyl‐1‐methoxymethyl‐4‐methyl‐2‐oxo‐1,2,3,4‐tetrahydroquinone. No significant breakdown products of bentazone could be identified.

  DOI：

  10.1002/etc.5620140805

文献信息

• Kinetics and Mechanism of the Nucleophilic Displacement Reactions of Chloroacetanilide Herbicides:  Investigation of α-Substituent Effects
  作者：Katrice A. Lippa、Sandra Demel、Irvin H. Lau、A. Lynn Roberts

  DOI：10.1021/jf030290d

  日期：2004.5.1

  ease with which alpha-chloroacetanilide herbicides undergo displacement reactions with strong nucleophiles, and their recalcitrance toward weak ones, is intimately related to their herbicidal properties and environmental chemistry. In this study, we investigate the kinetics and mechanisms of nucleophilic substitution reactions of propachlor and alachlor in aqueous solution. The role played by the alpha-amide

  α-氯代乙酰苯胺除草剂与强亲核体发生取代反应的难易程度以及对弱亲核体的拒服性与它们的除草特性和环境化学密切相关。在这项研究中，我们研究了水溶液中丙草胺和甲草胺的亲核取代反应的动力学和机理。通过包括具有修饰的α取代基的几种丙草胺的结构上相关的类似物，检查了α-酰胺基团所起的作用。反应的整体二级性质，负DeltaS（双匕首）值，离子强度对反应性的弱影响，结构反应性趋势共同支持分子间的S（N）2机理，而不是丙氯的α-氯代乙酰苯胺以及α-氯代硫代乙酰苯胺类似物的分子内反应。相反，α-亚甲基类似物表现出动力学和盐效应，与苯胺氮的邻氨基苯甲酸酯辅助相一致。可以推断出与α-苯胺取代基的电子相互作用，而不是与邻近基团的参与，可以控制α-氯乙酰苯胺对亲核试剂的反应性。
• NMR and Molecular Mechanics of Alachlor Conformation and Conformers: Implications to the Mechanism of Environmental Photodegradation
  作者：Walter F. Schmidt、Cathleen J. Hapeman、Rolland M. Waters、W. E. Johnson

  DOI：10.1021/jf00054a059

  日期：1995.6

  Hindered intramolecular free rotation around specific single bonds within alachlor accounts for the existence of the stable conformers observed in solution by NMR spectroscopy. NMR and molecular mechanics techniques enable identification of the molecular chemical environment under which specific conformations of alachlor are changed. Results suggest the photodegradation products previously reported have one of these conformers as a common intermediate. Chemical environments that increase the amount of this conformer could therefore enhance its rate of photodegradation. Chemical environments that stabilize a different conformation may have significantly longer half-lives or different photodegradation products.
• Occurrence of Alachlor Environmental Degradation Products in Groundwater
  作者：Thomas L. Potter、Thomas L. Carpenter

  DOI：10.1021/es00006a018

  日期：1995.6.1

  Groundwater samples collected beneath a Massachusetts corn field were analyzed by gas chromatography/mass spectrometry. In addition to alachlor, 20 compounds were detected whose El and CIMS data indicated that they were derived from alachlor, presumably via environmental degradation. Structural assignments were confirmed for six of these compounds by analysis of standards. They were among 10 alachlor-related compounds that were synthesized by use of either the parent compound or 2,6-diethylaniline as starting material. To our knowledge, none of the confirmed compounds have previously been reported in groundwater samples. The concentration range of the degradation products ranged from 4 to 570 ng L(-1). In all samples, the total concentration of the degradation products exceeded the parent compound concentration by at least 2-fold.
• CH596761
  申请人：——

  公开号：——

  公开（公告）日：——
• US3956388A
  申请人：——

  公开号：US3956388A

  公开（公告）日：1976-05-11