trans-4-<<<<(1R-trans)-3-<<<2-(phenylmethyl)-4-furyl>methoxy>carbonyl>-2,2-dimethyl-1-cyclopropyl>carbonyl>amino>methyl>cyclohexane-1-carboxylic acid | 151059-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: trans-4-<<<<(1R-trans)-3-<<<2-(phenylmethyl)-4-furyl>methoxy>carbonyl>-2,2-dimethyl-1-cyclopropyl>carbonyl>amino>methyl>cyclohexane-1-carboxylic acid
• CAS: 151059-60-8
• 化学式: C₂₇H₃₃NO₆
• 分子量: 467.562
• InChiKey: DLLCRZSYDNPEII-HMNCIZAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  105.84
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 trans-4-<<<<(1R-trans)-3-<<<2-(phenylmethyl)-4-furyl>methoxy>carbonyl>-2,2-dimethyl-1-cyclopropyl>carbonyl>amino>methyl>cyclohexane-1-carboxylic acid 在 N,N'-二环己基碳二亚胺 作用下， 以81%的产率得到(3R-trans)-3-<<<carbonyl>cyclohexyl>methyl>amino>carbonyl>-2,2-dimethylcyclopropane-1-carboxylic acid, <2-(phenylmethyl)-4-furyl>methyl 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：

  5-(苯基甲基)-3-呋喃甲醇 在 4-二甲氨基吡啶 、 四乙基氟化铵水合物 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.33h， 生成 trans-4-<<<<(1R-trans)-3-<<<2-(phenylmethyl)-4-furyl>methoxy>carbonyl>-2,2-dimethyl-1-cyclopropyl>carbonyl>amino>methyl>cyclohexane-1-carboxylic acid
  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