5-Acetyl-6,8-dibromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid | 151623-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Acetyl-6,8-dibromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
• 英文别名: 5-acetyl-6-bromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid；5-Acetyloxy-6,8-dibromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
• CAS: 151623-59-5
• 化学式: C₁₃H₁₂Br₂O₄
• 分子量: 392.044
• InChiKey: GUCKQMTXPORCSB-UHFFFAOYSA-N

物化性质

• 沸点：
  467.1±45.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Acetyl-6,8-dibromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到5-hydroxy-2-naphthoic acid
  参考文献：
  名称：

  Development of a Selective Enzyme-Linked Immunosorbent Assay for 1-Naphthol-the Major Metabolite of Carbaryl (1-Naphthyl N-Methylcarbamate)

  摘要：

  selective enzyme-linked immunosorbent assay for 1-naphthol was developed. Eight rabbits were immunized with either [(5-hydroxy-2-naphthylenyl)oxy]acetic acid (2b)-BSA, [(5-hydroxy-1-naphthylenyl)oxy]acetic acid (4)-BSA, or 5-hydroxy-2-naphthoic acid (7)-KLH, and all sera were screened against 14 different coating antigens. From this screening procedure, five assays could be developed, using two 7-KLH antisera, 3907 and 3909. The assay with the least interference and the best reliability (7-KLH antiserum 3907, 1:9000, and coating antigen 2b-BSA, 1.5 mu g/mL) was further optimized and characterized. It showed an I-50 value of about 72 mu g/L, with a range of detection from 10 to 1000 mu g/L. There was no cross-reactivity with carbaryl, which makes this assay very suitable for the selective detection of 1-naphthol, for example, in undiluted human urine and in soil extract. The assay was tested in organic solvents and showed a tolerance of at least 10% solvent (acetone, acetonitrile, methanol).

  DOI：

  10.1021/jf00040a019
• 作为产物：
  描述：

  7,8-dihydronaphthalene-2-carboxylic acid methyl ester 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 N-溴代乙酰胺 作用下， 以 甲醇 、 四氯化碳 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 5-Acetyl-6,8-dibromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Hapten design and development of an ELISA (enzyme-linked immunosorbent assay) for the detection of the mercapturic acid conjugates of naphthalene

  摘要：

  Measurement of urinary metabolites constitutes a noninvasive method to assess toxic exposure. Naphthalene is a common environmental contaminant showing selective pulmonary toxicity in mice and presumably is involved in development of lung disease in man (Buckpitt, A.R.; Franklin, R.B. Pharmacol. Ther. 1989, 41, 339). A glutathione-based detoxification pathway leads to the formation of the mercapturic acid conjugates [NaphMA 1, (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-1-hydroxy-2-naphthyl]cysteine] and (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-2-hydroxy-1-naphthyl]cysteine] which are excreted in urine. Herein we report the development of an immunoassay for the specific detection of these urinary metabolites. This study confirms the importance of appropriate hapten design and synthesis in controlling the specificity and sensitivity of the immunoassay. Our strategy was to prepare haptens that allow covalent attachment to a carrier protein at a site opposite to the N-acetylcysteine moiety. The antibodies obtained by immunizing six rabbits with these NaphMA derivatives (haptens 13 and 14) have been used for the development of an ELISA (enzyme-linked immunosorbent assay) which detects NaphMA 1 in the range between 100 and 6 pg/mL with an I50 of 29 pg/mL. Its ability to detect these important naphthalene metabolites in human urine is demonstrated.

  DOI：

  10.1021/jo00078a039