烯菌酮M2 | 83792-61-4

• 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: 烯菌酮M2
• 英文名称: N-(3,5-Dichlorophenyl)-2-hydroxy-2-methylbut-3-enanilide
• 英文别名: 3,5-dichlorophenyl-2-hydroxy-2-methylbut-3-enanilide；3',5'-dichloro-2-hydroxy-2-methylbut-3-enanilide；M2；N-(3,5-dichlorophenyl)-2-hydroxy-2-methylbut-3-enamide
• CAS: 83792-61-4
• 化学式: C₁₁H₁₁Cl₂NO₂
• 分子量: 260.12
• InChiKey: FBYYIBNYONAZCU-UHFFFAOYSA-N

物化性质

• 沸点：
  426.9±45.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)
• 溶解度：
  DMF: 30 mg/ml,DMSO: 30 mg/ml,乙醇: 30 mg/ml,乙醇:PBS (pH 7.2)(1:1): .5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  烯菌酮M2 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 生成 3',5'-dichloro-2,3,4-trihydroxy-2-methylbutyranilide
  参考文献：
  名称：

  Vinclozolin在大鼠精密切割肝脏切片中的生物转化：与体内代谢模式的比较。

  摘要：

  Vinclozolin是一种二羧酰亚胺杀真菌剂，通过其两个与雄激素受体结合的水解产物M1和M2表现出抗雄激素特性。由于缺乏关于vinclozolin的生物转化的数据，使用[（14）C] -vinclozolin在精确切割的大鼠肝切片中体外研究了其代谢，在雄性大鼠体内研究了vinclozolin的代谢。使用不同浓度的底物进行孵育，并研究了主要代谢物形成的动力学。用[[14）C] -VZ饲喂三只雄性Wistar大鼠。收集尿液24小时，并通过放射-HPLC分析其代谢谱。代谢物鉴定是在LCQ离子阱质谱仪上进行的。在大鼠肝脏切片和体内，主要的主要代谢产物已被鉴定为3'，5'-dichloro-2,3，4-三羟基-2-甲基丁酰苯胺（M5），主要以葡萄糖醛酸偶联物的形式存在。M5是通过M2的乙烯基二羟基化产生的。其他代谢物已被确定为3-（3,5-二氯苯基）-5-甲基-5-（1,2-二羟乙基）-1,3-恶唑烷-2

  DOI：

  10.1021/jf0728045
• 作为产物：
  描述：

  乙烯菌核利 在 potassium dihydrogenphosphate 、 水 、 magnesium chloride 作用下， 生成 烯菌酮M2
  参考文献：
  名称：

  人肝微粒体在体外对Vinclozolin进行I期代谢。

  摘要：

  1. Vinclozolin（Vin）是一种用于农业环境的杀菌剂，被归类为内分泌干扰物。Vin被非酶水解为2-[[（（3,5-二氯苯基）-氨基甲酰基]氧基] -2-甲基-3-丁烯酸（M1）和3'，5'-二氯-2-羟基-2-甲基丁-3-烯胺（M2）代谢产物。目前尚无有关人类中Vin生物转化的信息，因此，本研究的目的是利用人肝微粒体表征其Vintro体外代谢。 2. Vin代谢为[3-（3,5-二氯苯基）-5-甲基-5-（1,2-二羟乙基）-1,3-恶唑烷-2,4-二酮]（M4）和N- （2,3,4-三羟基-2-甲基-1-氧代）-3,5-二氯苯基-1-氨基甲酸（M7）代谢产物，不稳定并逐渐转化为3'，5'-dichloro-2， 3，4-三羟基-2-甲基丁酰苯胺（DTMBA，以前表示为M5）。M4和DTMBA代谢物在同一HPLC峰中共洗脱; 该共洗脱峰显示出Michaelis-Menten动力

  DOI：

  10.1080/00498254.2018.1523485

文献信息

• Chemical and Biological Transformation of the Fungicide Vinclozolin
  作者：Christine Mercadier、Danielle Vega、Jean Bastide

  DOI：10.1021/jf980275m

  日期：1998.9.1

  Two mixed bacterial cultures were isolated from a French soil adapted to the dicarboximide fungicide vinclozolin. The vinclozolin was transformed by the mixed bacterial cultures according to two degradation pathways: (a) the formation of 2-[[(3,5-dichlorophenyl)carbamoyl]oxy]-2-methyl-3- butenoic acid and then 3,5-dichloroaniline or (b) the formation of 3',5'-dichloro-2-hydroxy-2-methylbut-3-enanilide and then 3,5-dichloroaniline. The structure of 2-[[(3,5-dichlorophenyl)carbamoyl]oxy]-2-methyl-3-butenoic acid was unambiguously established by H-1 and C-13 2-D NMR analysis. A bacterial strain isolated from soil that degrades this compound was identified as;a strain of Corynebacterium sp. Attempts to obtain pure vinclozolin-degrading strains via 3',5'-dichloro-2-hydroxy-2-methylbut-3-enanilide were unsuccessful.
• Alkaline hydrolysis of vinclozolin: Effect of humic acids aggregates in water
  作者：J. Morales、A. Cid、J.C. Mejuto

  DOI：10.1016/j.molcata.2015.02.017

  日期：2015.5

  The influence of natural organic substances as humate colloidal aggregates in water solutions upon the chemical stability of vinclozolin has been investigated in basic media. A large inhibition (9 times-fold) has been observed and it has been rationalized in terms of a micellar pseudophase model. The observed behaviour could increase significantly the half-life of this fungicide. Moreover, these experimental results have been compared with the corresponding ones of other substances in these natural colloidal aggregates. (C) 2015 Elsevier B.V. All rights reserved.
• Kinetics and mechanisms of hydrolysis of dicarboximide fungicides in micellar media
  作者：Jean C. Villedieu、Alain de Savignac、Jean P. Calmon

  DOI：10.1021/jf00055a035

  日期：1995.7

  The kinetics of alkaline hydrolysis of the dicarboximide fungicides procymidone, iprodione, vinclozolin, and chlozolinate (1-4, respectively) were investigated in micellar solutions containing various amounts of either sodium dodecyl sulfate (SDS), cetyltrimethylammonium bromide (CTAB), or three nonionic surfactants (two C-13 alcohols and a copra amine combined with ethoxyl chains) and compared with the kinetics in aqueous media. For all compounds, the rate constants observed are slightly reduced by the SDS micellar media, showing that reactions essentially take place in the aqueous pseudophase. The CTAB micellar media speed up the hydrolysis rates with small quantities of Br- ions in the medium. As the number of Br- ions increases, the rate of reactions falls. This is characteristic of an ion exchange (OH- and Br-) at the surface of the CTAB micelles. Finally, the presence of nonionic micelles has little influence on the hydrolysis of the fungicides: the reduction in the rate of dicarboximide ring opening is attributed to micelle-substrate association. These results can be explained by means of the pseudophase kinetic model coupled with the mechanisms of hydrolysis of these fungicides in water solution.
• Mechanisms of dicarboximide ring opening in aqueous media: Procymidone, vinclozolin and chlozolinate
  作者：Jean C. Villedieu、Michelle Calmon、Jean P. Calmon

  DOI：10.1002/ps.2780410206

  日期：1994.6

  AbstractThe hydrolysis kinetics of the dicarboximide fungicides procymidone, vinclozolin and chlozolinate in neutral and alkaline solutions of pH 60 to 13·7 at 25°C have been determined conjointly by ultraviolet spectrophotometry and by high performance liquid chromatography. Under alkaline conditions, the fungicides undergo attack by the hydroxide ion on a specific carbonyl group and the rate of hydrolysis increases proportionally to the hydroxide ion concentration. Procymidone gives quantitatively and irreversibly 2‐(3,5‐dichlorophenylcarba‐moyl)‐l,2‐dimethylcyclopropanecarboxylate. The reaction is not subject to general base catalysis and experimental data are in agreement with a rate‐determining attack by the hydroxide ion. After a rapid hydrolytic loss of the ethoxycarbonyl substituent from chlozolinate, the dicarboximide ring cleavage of the two other fungicides leads, by mechanisms which differ with respect to the type of base catalysis and the rate‐determining step, to the corresponding anilides, producing as intermediates the carbamic acids, which undergo loss of carbon dioxide. The hydrolysis of vinclozolin and chlozolinate yields, respectively, N‐(3,5‐dichloro‐phenyt)‐2‐hydroxy‐2‐methylbut‐3‐enanilide and N‐(3,5‐dichlorophenyl)‐2‐hydroxy‐propanilide.
• SZETO, SUNNY Y.;BURLINSON, NICK E.;RAHE, JAMES E.;OLOFFS, PETER C., J. AGR. AND FOOD CHEM., 37,(1989) N, C. 523-529
  作者：SZETO, SUNNY Y.、BURLINSON, NICK E.、RAHE, JAMES E.、OLOFFS, PETER C.

  DOI：——

  日期：——