反式-1-(3,4-二氯苯基)-3-(三氟甲基)戊-1-烯-4-炔-3-醇 | 101048-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 中文名称: 反式-1-(3,4-二氯苯基)-3-(三氟甲基)戊-1-烯-4-炔-3-醇
• 英文名称: trans-1-(3,4-dichlorophenyl)-3-(trifluoromethyl)pent-1-en-4-yn-3-ol
• 英文别名: (E)-1-(3,4-dichlorophenyl)-3-(trifluoromethyl)pent-1-en-4-yn-3-ol
• CAS: 101048-02-6
• 化学式: C₁₂H₇Cl₂F₃O
• 分子量: 295.088
• InChiKey: PVLJQWKGGYCKCW-AATRIKPKSA-N

物化性质

• 沸点：
  386.3±42.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  反式-1-(3,4-二氯苯基)-3-(三氟甲基)戊-1-烯-4-炔-3-醇 在 硫酸 、 mercury(II) oxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以21%的产率得到5-(3,4-dichlorophenyl)-3-hydroxy-3-trifluoromethylpent-trans 4-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
• 作为产物：
  描述：

  3,4-二氯苯甲醛 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 反式-1-(3,4-二氯苯基)-3-(三氟甲基)戊-1-烯-4-炔-3-醇
  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：EP0154528A2

  公开（公告）日：1985-09-11

  A compound of the formula wherein X has the formula wherein ring A is phenyl, naphthyl or heterocyclic; wherein R' is hydrogen, alkyl, alkanoyl or aroyl; wherein R2, R3 and R4, 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 R2, R3 and R4 is an electron-withdrawing substituent; wherein R5 and R6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R7 is alkyl or halogenoalkyl; and wherein RS is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R8 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 R8 has the formula wherein ring B is phenyl, naphthyl or heterocyclyl and wherein R2, R3 and R4 have any of the meanings stated above, provided that when R7 is methyl R8 is not also methyl.

  式中的化合物 其中 X 具有式 其中环 A 是苯基、萘基或杂环； 其中 R' 是氢、烷基、烷酰基或芳基；其中 R2、R3 和 R4（可以相同或不同）各自是选自卤代、硝基、氰基、三氟甲基、烷硫基、烷基亚磺酰基和烷基磺酰基的抽电子取代基，或者各自是氢、烷基、烷氧基或二烷基氨基，条件是当环 A 是苯基或萘基时，R2、R3 和 R4 中至少有一个是抽电子取代基；其中R5和R6可以相同或不同，各自为氢、卤素或烷基； 其中R7为烷基或卤代烷基；其中 RS 是氨基甲酰基、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基；或其中 R8 是烷基或烯基，带有一个或多个取代基，选自氰基、氨基甲酰基、氨基、羟基、烷酰基、烷氧基、烷硫基、烯硫基、烷基亚磺酰基、烯基亚磺酰基、烷基磺酰基、烯基磺酰基、烷酰氨基、烷氧羰基氨基、烷基磺酰胺、烷基氨基、二烷基氨基、二烷基磺酰胺酰基、芳基、芳硫基、芳基亚砜基、芳基磺酰基、杂环亚砜基、杂环亚砜基和杂环磺酰基；或其中 R8 具有以下式子 其中环 B 是苯基、萘基或杂环基，R2、R3 和 R4 具有上述任何一种含义，但 R7 是甲基时，R8 不也是甲基。
• 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：——
• 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