[3-(cyanohydroxymethyl)phenoxy]acetic acid benzyl ester | 474457-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-(cyanohydroxymethyl)phenoxy]acetic acid benzyl ester
• CAS: 474457-55-1
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: DXYDKCIEQRKNDG-UHFFFAOYSA-N

物化性质

• 沸点：
  490.1±45.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.55
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [3-(cyanohydroxymethyl)phenoxy]acetic acid benzyl ester 在 吡啶 、 碘代三甲硅烷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 2.5h， 生成 3-[(+/-)-cyano[1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyloxy]methyl]phenoxyacetic acid
  参考文献：
  名称：

  Enzyme-Linked Immunosorbent Assay for the Pyrethroid Deltamethrin

  摘要：

  A competitive enzyme-linked immunosorbent assay (ELISA) for the detection of deltamethrin was developed. Two haptens, cyano[3 (4 aminophenoxy)phenyl]methyl 1R cis 3 (2,2-dibromoethenyl) 2,2- dimethylcyclopropanecarboxylate and 3 [(+/-) cyano[1R cis 3 (2,2-dibromoethenyl) 2,2-dimethylcyclopropan ecarbonyloxy]methyl]phenoxyacetic acid, were synthesized and conjugated with thyroglobulin as immunogens. Four antisera were generated and screened against six different coating antigens. The assay that was the most sensitive for deltamethrin was optimized and characterized. The I-50 for deltamethrin was 17.5 +/- 3.6 mug/L, and the lower detection limit was 1.1 +/- 0.5 mug/L. This ELISA assay had relatively low cross reactivities with other major pyrethroids such as permethrin phenothrin, bioresmethrin cyfluthrin, and cypermethrin. Methanol was found to be the best organic cosolvent for this ELISA, with optimal sensitivity observed at a concentration of 40% (v/v). The assay parameters were unchanged at pH values between 5.0 and 8.0 whereas higher ionic strengths strongly suppressed the absorbances. To increase the sensitivity of the overall method, a C-18 sorbent based solid phase extraction was used for river water samples. River water samples fortified with deltamethrin were analyzed according to this method. Good recoveries and correlation with spike levels were observed.

  DOI：

  10.1021/jf0207629
• 作为产物：
  描述：

  3-甲酰基苯氧基乙酸 在 硫酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 [3-(cyanohydroxymethyl)phenoxy]acetic acid benzyl ester
  参考文献：
  名称：

  Development of an Enzyme-Linked Immunosorbent Assay for the Pyrethroid Insecticide Cyhalothrin

  摘要：

  A competitive enzyme-linked immunosorbent assay ( ELISA) was developed for detection of the pyrethroid insecticide cyhalothrin. Three haptens with an amine or propanoic acid terminus were synthesized and then conjugated with bovine serum albumin to give immunogens. Eight polyclonal antisera produced by rabbits were screened for titers and affinity using three different coating antigens. The antiserum CWB-C had the highest affinity with cyhalothrin and a low affinity with fenvalerate, fenpropathrin, deltamethrin, and fluvalinate. The half-maximum inhibition concentration for cyhalothrin was 37.2 mu g/L, and the limit of detection was 4.7 mu g/L. The recoveries of different concentrations of cyhalothrin (0.1-2500 mu g/L) from fortified tap water, well water, and wastewater samples as determined with the ELISA were 81-114%.

  DOI：

  10.1021/jf0607009

文献信息

• Enzyme-Linked Immunosorbent Assay for the Pyrethroid Permethrin
  作者：Guomin Shan、Whitney R Leeman、Donald W. Stoutamire、Shirley J. Gee、Daniel P. Y. Chang、Bruce D. Hammock

  DOI：10.1021/jf000351x

  日期：2000.9.1

  Permethrin is a predominant pyrethroid widely used in agriculture and public health. A competitive enzyme-linked immunosorbent assay (ELISA) for the detection of permethrin was developed. Two haptens, the trans- and cis-isomers of 3-(4-aminophenoxy)benzyl-3-(2, 2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate, were synthesized and conjugated with thyroglobulin as immunogens. Four antisera were

  苄氯菊酯是主要用于农业和公共卫生的拟除虫菊酯。开发了一种竞争性酶联免疫吸附测定（ELISA），用于检测氯菊酯。合成了两个半抗原，即3-（4-氨基苯氧基）苄基-3-（2,2-二氯乙烯基）-2,2-二甲基环丙烷羧酸酯的反式和顺式异构体，并与甲状腺球蛋白作为免疫原偶联。产生了四种抗血清，并针对六种不同的包被抗原进行了筛选。所得ELISA的I（50）值为2.50 microg / L，并且与其他主要拟除虫菊酯（如esfenvalerate，氯氰菊酯，溴氰菊酯和氯氟菊酯）的交叉反应性相对较低。发现甲醇是此ELISA的最佳溶剂，在​​浓度为40％（v / v）时观察到最佳灵敏度。pH值在5.0和8.0之间时，测定参数不变，而较高的离子强度（> 0.2 M PBS）会强烈抑制吸光度。根据该方法分析了用苄氯菊酯强化的河水样品，并通过GC-MS进行了验证。观察到良好的回收率和与峰值水平的相关性，这表明该免疫
• Development of an Enzyme-Linked Immunosorbent Assay for the Detection of the Pyrethroid Insecticide Fenpropathrin
  作者：Ingrid Wengatz、Donald W. Stoutamire、Shirley J. Gee、Bruce D. Hammock

  DOI：10.1021/jf9710847

  日期：1998.6.1

  A competitive enzyme-linked immunosorbent assay (ELISA) was developed for the quantitative detection of fenpropathrin [(RS)-alpha-cyano-3-phenoxybenzyl-2,2,3,3-tetramethylcyclopropanecarboxylate]. Polyclonal antisera were isolated from rabbits immunized with two different fenpropathrin hapten conjugates. One hapten contained an amino function; the other contained a carboxyl group for conjugation to carrier proteins. Mollusk hemocyanins, thyroglobulin, and fetuin were used as carrier proteins. The antisera varied greatly in their affinities for fenpropathrin. A homologous assay system using the coating antigen format was the most sensitive. The IC50 for fenpropathrin was 20 mu g/L, and the lower detection limit was 2.5 mu g/L. Pyrethroids, such as phenothrin, permethrin, resmethrin, fenvalerate, deltamethrin, cyfluthrin, and cypermethrin, and the pyrethroid metabolites, 3-phenoxybenzoic acid and fenpropathrin acid, did not cross-react significantly in this assay. Ten percent acetone or methanol and a pH of 4 were determined to be optimum assay conditions. Various cationic, anionic, and nonionic detergents had no significant effect on the assay.
• Development of an Immunoassay for the Pyrethroid Insecticide Esfenvalerate
  作者：Guomin Shan、Donald W. Stoutamire、Ingrid Wengatz、Shirley J. Gee、Bruce D. Hammock

  DOI：10.1021/jf981210m

  日期：1999.5.1

  A competitive enzyme-linked immunosorbent assay was developed for the detection of the pyrethroid insecticide esfenvalerate. Two haptens containing amine or propanoic acid groups on the terminal aromatic ring of the fenvalerate molecule were synthesized and coupled to carrier proteins as immunogens. Five antisera were produced and screened against eight different coating antigens. The assay that had the least interference and was the most sensitive for esfenvalerate was optimized and characterized. The I-50 for esfenvalerate was 30 +/- 6.2 mu g/L, and the lower detection limit (LDL) was 3.0 +/- 1.8 mu g/L. The assay was very selective. Other pyrethroid analogues and esfenvalerate metabolites tested did not cross-react significantly in this assay. To increase the sensitivity of the overall method, a C-18 sorbent-based. solid-phase extraction (SPE) was used for water matrix. With this SPE step, the LDL of the overall method for esfenvalerate was 0.1 mu g/L in water samples.