ethyl 3-(2-chloro-4-cyanophenyl)propanoate | 80762-32-9

• 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: ethyl 3-(2-chloro-4-cyanophenyl)propanoate
• 英文别名: Ethyl 3-(chloro-4-cyanophenyl)propanoate
• CAS: 80762-32-9
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: DGCGEBKTVXIHLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-chloro-4-cyanophenyl)propanoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以63%的产率得到3-(2-chloro-4-cyanophenyl)propanoic acid
  参考文献：
  名称：

  用于安非他酮放射免疫测定的半抗原的设计与合成

  摘要：

  描述了可用于安非他酮放射免疫测定的半抗原的合成。由于安非他酮不具有易于衍生的官能团，因此将羟丙基引入分子中。与可能的代谢物的交叉反应性研究要求合成安非他酮的4'-羟基类似物。还描述了这种合成。

  DOI：

  10.1002/jps.2600750420
• 作为产物：
  描述：

  3-氯-4-甲基苯甲腈 在 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium ethanolate 、 sodium chloride 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 ethyl 3-(2-chloro-4-cyanophenyl)propanoate
  参考文献：
  名称：

  用于安非他酮放射免疫测定的半抗原的设计与合成

  摘要：

  描述了可用于安非他酮放射免疫测定的半抗原的合成。由于安非他酮不具有易于衍生的官能团，因此将羟丙基引入分子中。与可能的代谢物的交叉反应性研究要求合成安非他酮的4'-羟基类似物。还描述了这种合成。

  DOI：

  10.1002/jps.2600750420

文献信息

• Compounds and methods of making same
  申请人：Burroughs Wellcome Co.

  公开号：US04347176A1

  公开（公告）日：1982-08-31

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --0--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--0--(CH.sub.2).sub.q --COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NO(CH.sub.2).sub.q CO--X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n --0--(CO).sub.m --(CH.sub.2).sub.p --CO--X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  已发现了一种用于生物液体中抗抑郁化合物丙酮莫林[(.+-.)-2-t-丁基氨基-3-氯丙酮]的放射免疫分析程序。公开了一系列新颖化合物的公式，其中R.sub.2为氧，R.sub.1为(CH.sub.2).sub.n--0--(CO).sub.m--(CH.sub.2).sub.p--COOH，其中n为0至5的整数，m为0或1，p为1至4的整数；或者R.sub.1为氢，R.sub.2为N--0--(CH.sub.2).sub.q--COOH，其中q为1至3的整数，并公开了制备它们以及其中有用的新颖中间体的新方法。公开了用于产生丙酮莫林特异抗血清的新免疫原以及制备它们的新方法，其中包括新化合物和适当载体材料的结合物。药物与新的放射标记竞争物质一起加入到抗血清中，该竞争物质的公式为##STR2##，其中R'是如上所述的适当放射性同位素，R.sub.3是氢，R.sub.4是氯，R.sub.5是氧，或者R'是氢，且(a)R.sub.3是H，R.sub.4是Cl，R.sub.5是NO(CH.sub.2).sub.qCO--X，其中q如公式I所定义，X是具有公式III的基团##STR3##，其中R.sub.6是如上所述的适当放射性同位素，R.sub.7是羟基，s是1至4的整数；(b)R.sub.4是Cl，R.sub.5是氧，R.sub.3是(CH.sub.2).sub.n--0--(CO).sub.m--(CH.sub.2).sub.p--CO--X，其中n，m和p如公式I所定义，X如上所定义；或者(c)R.sub.3是羟基，R.sub.5是氧，R.sub.4是如上所定义的适当放射性同位素。抗血清结合的放射标记竞争物的放射活性测量提供了测定生物液体样品中药物量的测量值。可以从标准曲线中构建出药物在测定样品中的量。公开了用于进行放射免疫分析的试剂盒。
• Compounds and methods of making them
  申请人：Burroughs Wellcome Co.

  公开号：US04347177A1

  公开（公告）日：1982-08-31

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--O--(CH.sub.2).sub.q --COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NO(CH.sub.2).sub.q CO--X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --CO--X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  一种用于在生物液体中检测抗抑郁化合物丁腈羟考酮的放射免疫分析方法已被发现。其中一些新化合物的公式为##STR1## 其中R.sub.2为氧，R.sub.1为(CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH，其中n为0至5的整数，m为0或1，p为1至4的整数；或者R.sub.1为氢，R.sub.2为N--O--(CH.sub.2).sub.q --COOH，其中q为1至3的整数。还揭示了制备这些新化合物的新方法和有用的新中间体。揭示了用于提高丁腈羟考酮特异性抗血清的新免疫原和制备它们的新方法，包括新化合物和适当载体材料的结合物。将药物与放射性标记的竞争物质一起加入抗血清中，所述竞争物质的公式为##STR2## 其中R'为适当的放射性同位素，R.sub.3为氢，R.sub.4为氯，R.sub.5为氧，或者R'为氢，且(a)R.sub.3为H，R.sub.4为Cl，R.sub.5为NO(CH.sub.2).sub.q CO--X，其中q如公式I所定义，X为具有公式III的基团##STR3## 其中R.sub.6为适当的放射性同位素，R.sub.7为羟基，s为1至4的整数；(b)R.sub.4为Cl，R.sub.5为氧，R.sub.3为(CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --CO--X，其中n，m和p如公式I所定义，X如上所述；或(c)R.sub.3为羟基，R.sub.5为氧，R.sub.4为如上所定义的适当放射性同位素。抗血清结合放射性标记竞争物质的放射性测量提供了检测生物液体样品中药物量的测量值。可以从标准曲线中构建插值出检测样品中药物量。还揭示了用于实施放射免疫分析的套件。
• 3.sup.H Labeled compounds
  申请人：Burroughs Wellcome Co.

  公开号：US04347382A1

  公开（公告）日：1982-08-31

  A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n -0-(CO).sub.m -(CH.sub.2).sub.p -COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N-O-(CH.sub.2).sub.q -COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is CL, and R.sub.5 is oxygen, or R' is hydrogen and either (a) R.sub.3 is H and R.sub.4 is Cl and R.sub.5 is NC(CH.sub.2).sub.q CO-X where q is as defined for formula I and X is a group having formula III ##STR3## wherein R.sub.6 is a suitable radioisotope as described above, R.sub.7 is hydroxyl, and s is an integer from 1 to 4; (b) R.sub.4 is Cl, R.sub.5 is oxygen, and R.sub.3 is (CH.sub.2).sub.n -0-(CO).sub.m -(CH.sub.2).sub.p -CO-X where n, m, and p are as defined for formula I and X is as defined above; or (c) R.sub.3 is hydroxy, R.sub.5 is oxygen and R.sub.4 is a suitable radioisotope as defined above. The measure of radioactivity of the antisera bound radiolabeled competitor provides a measure of the amount of drug in the assayed biological fluid sample. A standard curve can be constructed from which the amount of drug in the assay sample can be interpolated. A kit is disclosed for practicing the radioimmunoassay.

  一种用于生物液体中抗抑郁化合物bupropion [(+/-)-2-t-丁基氨基-3-氯代丙酮]的放射免疫测定程序已被发现。公开了新的化合物的公式，其中R.sub.2为氧，R.sub.1为(CH.sub.2).sub.n-0-(CO).sub.m-(CH.sub.2).sub.p-COOH，其中n为0到5的整数，m为0或1，p为1到4的整数；或R.sub.1为氢，R.sub.2为N-O-(CH.sub.2).sub.q-COOH，其中q为1到3的整数，并公开了制备它们的新方法和有用的新中间体。公开了用于提高bupropion特异性抗血清的新免疫原和制备它们的新方法，其中包括新化合物和适当载体材料的结合物。将药物加入抗血清中，与公式中的新放射性标记竞争物一起，其中R'是适当的放射性同位素，如上述所述，R.sub.3是氢，R.sub.4是CL，R.sub.5是氧，或R'是氢，且（a）R.sub.3为H，R.sub.4为Cl，R.sub.5为NC(CH.sub.2).sub.qCO-X，其中q如公式I所定义，X是具有公式III的组，其中R.sub.6是适当的放射性同位素，如上述所述，R.sub.7是羟基，s是1到4的整数；（b）R.sub.4为Cl，R.sub.5为氧，R.sub.3为（CH.sub.2).sub.n-0-(CO).sub.m-(CH.sub.2).sub.p-CO-X，其中n、m和p如公式I所定义，X如上所述；或（c）R.sub.3为羟基，R.sub.5为氧，R.sub.4是上述所定义的适当的放射性同位素。抗血清结合的放射标记竞争物的放射性测量提供了测定生物液体样品中药物量的测量。可以从标准曲线中构建出药物在测定样品中的量。公开了用于实施放射免疫测定的试剂盒。
• MEHTA, N. B.
  作者：MEHTA, N. B.

  DOI：——

  日期：——
• New unlabelled and radioactive labelled derivatives of butylamino propiophenone, their preparation, immunogens obtained from the unlabelled derivatives and a process for immunogen preparation, antisera raised using the immunogens and a method for raising antisera, a radioimmunoassay method and a test kit for use in the assay method
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0038071B1

  公开（公告）日：1984-11-14