1,1,1-trifluoro-4-(3,4-dichlorophenyl)but-trans-3-en-2-one | 101047-45-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,1,1-trifluoro-4-(3,4-dichlorophenyl)but-trans-3-en-2-one
• 英文别名: trans-4-(3',4'-dichlorophenyl)-1,1,1-trifluorobut-3-en-2-one；1,1,1-trifluoro-4-(3,4-dichlorophenyl)but-trans-3-ene-2-one；(E)-4-(3,4-dichlorophenyl)-1,1,1-trifluorobut-3-en-2-one
• CAS: 101047-45-4
• 化学式: C₁₀H₅Cl₂F₃O
• 分子量: 269.05
• InChiKey: BYMBYXJUEHLHAL-DUXPYHPUSA-N

物化性质

• 沸点：
  274.0±40.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-4-(3,4-dichlorophenyl)but-trans-3-en-2-one 在 正丁基锂 、 magnesium chloride 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 1-chloro-4-(3,4-dichlorophenyl)-2-trifluoro-methylbut-trans-3-en-2-ol
  参考文献：
  名称：

  Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens

  摘要：

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.

  DOI：

  10.1021/jm00105a067
• 作为产物：
  描述：

  1,1,1-三氟丙酮 、 3,4-二氯苯甲醛 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以21%的产率得到1,1,1-trifluoro-4-(3,4-dichlorophenyl)but-trans-3-en-2-one
  参考文献：
  名称：

  Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens

  摘要：

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.

  DOI：

  10.1021/jm00105a067

文献信息

• Alkene, alkyne or cycloalkylene derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US04873329A1

  公开（公告）日：1989-10-10

  A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.8 is alkyl or alkenyl which bears one or more substituents selected from cyano, carbamoyl, amino, hydroxy, alkanoyl, alkoxy, alkylthio, alkenylthio, alkylsulphinyl, alkenylsulphinyl, alkylsulphonyl, alkenylsulphonyl, alkanoylamino, alkoxycarbonylamino, alkylsulphonamido, alkylamino, dialkylamino, dialkylsulphamoyl, aroyl, aryl, arylthio, arylsulphinyl, arylsulphonyl, heterocyclylthio, heterocyclylsulphinyl and heterocyclylsulphonyl; or wherein R.sup.8 has the formula ##STR3## wherein ring B is phenyl, naphthyl or heterocyclyl and wherein R.sup.2, R.sup.3 and R.sup.4 have any of the meanings stated above, provided that when R.sup.7 is methyl R.sup.8 is not also methyl.

  该化合物的化学式为 ##STR1## 其中X的化学式为 ##STR2## 其中环A为苯基、萘基或杂环基；其中R.sup.1为氢、烷基、烷酰基或芳香酰基；其中R.sup.2、R.sup.3和R.sup.4，可以相同也可以不同，每个都是从卤素、硝基、氰基、三氟甲基、烷基硫、烷基亚磺酰基和烷基磺酰基中选择的电子提取基团，或每个都是氢、烷基、烷氧基或二烷基氨基，但当环A为苯基或萘基时，R.sup.2、R.sup.3和R.sup.4中至少有一个是电子提取基团；其中R.sup.5和R.sup.6，可以相同也可以不同，每个都是氢、卤素或烷基；其中R.sup.7为烷基或卤代烷基；其中R.sup.8为氨基甲酰基、烷基、环烷基、烯基、炔基、卤代烷基、卤代烯基、卤代炔基、烷酰基、烷基氨基甲酰基、二烷基氨基甲酰基或芳香酰基；或者R.sup.8为带有一个或多个取自氰基、氨基、羟基、烷酰基、烷氧基、烷基硫、烯基硫、烷基亚磺酰基、烯基亚磺酰基、烷基磺酰基、烯基磺酰基、烷基氨甲酰基、烷氧羰基氨基、烷基磺酰胺基、烷基氨基、二烷基磺酰胺基、芳香酰基、芳香基、芳香基硫、芳香基亚磺酰基、芳香基磺酰基、杂环基硫、杂环基亚磺酰基和杂环基磺酰基中的一种或多种取代基的烷基或烯基；或者R.sup.8具有以下公式 ##STR3## 其中环B为苯基、萘基或杂环基，R.sup.2、R.sup.3和R.sup.4具有上述任何含义，但当R.sup.7为甲基时，R.sup.8不是甲基。
• MORRIS, JEFFREY J.;HUGHES, LESLIE R.;GLEN, ALASDAIR T.;TAYLOR, PETER J., J. MED. CHEM., 34,(1991) N, C. 447-455
  作者：MORRIS, JEFFREY J.、HUGHES, LESLIE R.、GLEN, ALASDAIR T.、TAYLOR, PETER J.

  DOI：——

  日期：——
• US4845119A
  申请人：——

  公开号：US4845119A

  公开（公告）日：1989-07-04
• US4873329A
  申请人：——

  公开号：US4873329A

  公开（公告）日：1989-10-10
• US5032592A
  申请人：——

  公开号：US5032592A

  公开（公告）日：1991-07-16