2-(trimethylsilyl)ethyl 4-hydroxybutanoate | 136586-84-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(trimethylsilyl)ethyl 4-hydroxybutanoate
• 英文别名: 2-Trimethylsilylethyl 4-hydroxybutanoate
• CAS: 136586-84-0
• 化学式: C₉H₂₀O₃Si
• 分子量: 204.341
• InChiKey: IBYNLZVLCRZLTH-UHFFFAOYSA-N

物化性质

• 沸点：
  266.3±20.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-trans-chrysanthemoyl chloride 、 2-(trimethylsilyl)ethyl 4-hydroxybutanoate 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid, 4-<2-(trimethylsilyl)ethoxy>-4-oxobutyl ester 、 (1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid, 2-(trimethylsilyl)ethyl ester
  参考文献：
  名称：

  Quantitation of bioresmethrin, a synthetic pyrethroid grain protectant, by enzyme immunoassay

  摘要：

  An enzyme immunoassay was developed for the synthetic pyrethroid, bioresmethrin, by use of a novel approach for synthesis of the pyrethroid-protein hapten conjugate for antibody preparation. Bioresmethrin was hydrolyzed at the ester linkage, and following protection of the chrysanthemic acid group, the 2-methylprop-1-ene substituent was oxidatively cleaved. The newly formed and unprotected acid group was reesterified to the other bioresmethrin hydrolysis product [[2-(phenylmethyl)-4-furyl]-methanol], and following substitution of the protecting group, the hapten was coupled to either protein for antibody production or peroxidase for use in the immunoassay. The most sensitive assay employed an antibody prepared to a derivative with a 4-carbon spacer arm between bioresmethrin and carrier protein, but used a bioresmethrin-enzyme reporter prepared using a 4-(aminomethyl)cyclohexane-carboxylic acid spacer arm (limit of detection 2 ppb in buffer, 50 ppb in whole wheat or barley grain). Good correlations between HPLC and ELISA determinations of bioresmethrin in whole or ground barley grain were obtained. The sensitivity of the assay was slightly lower in ground grain or flour milling fractions due to interference from coextractives in methanol extracts. Apart from resmethrin, of which bioresmethrin is the 1R,3R-trans-isomer, the assay did not detect a variety of other pyrethroids in commercial use.

  DOI：

  10.1021/jf00035a038
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 在 吡啶 、 sodium tetrahydroborate 、 氯甲酸乙酯 作用下， 以 二氯甲烷 为溶剂， 生成 2-(trimethylsilyl)ethyl 4-hydroxybutanoate
  参考文献：
  名称：

  Quantitation of bioresmethrin, a synthetic pyrethroid grain protectant, by enzyme immunoassay

  摘要：

  An enzyme immunoassay was developed for the synthetic pyrethroid, bioresmethrin, by use of a novel approach for synthesis of the pyrethroid-protein hapten conjugate for antibody preparation. Bioresmethrin was hydrolyzed at the ester linkage, and following protection of the chrysanthemic acid group, the 2-methylprop-1-ene substituent was oxidatively cleaved. The newly formed and unprotected acid group was reesterified to the other bioresmethrin hydrolysis product [[2-(phenylmethyl)-4-furyl]-methanol], and following substitution of the protecting group, the hapten was coupled to either protein for antibody production or peroxidase for use in the immunoassay. The most sensitive assay employed an antibody prepared to a derivative with a 4-carbon spacer arm between bioresmethrin and carrier protein, but used a bioresmethrin-enzyme reporter prepared using a 4-(aminomethyl)cyclohexane-carboxylic acid spacer arm (limit of detection 2 ppb in buffer, 50 ppb in whole wheat or barley grain). Good correlations between HPLC and ELISA determinations of bioresmethrin in whole or ground barley grain were obtained. The sensitivity of the assay was slightly lower in ground grain or flour milling fractions due to interference from coextractives in methanol extracts. Apart from resmethrin, of which bioresmethrin is the 1R,3R-trans-isomer, the assay did not detect a variety of other pyrethroids in commercial use.

  DOI：

  10.1021/jf00035a038