(E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-buten-2-one | 101048-67-3

• 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: (E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-buten-2-one
• 英文别名: (E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-butene-2-one；(E)-4-(2,4-difluorophenyl)-1,1,1-trifluorobut-3-en-2-one
• CAS: 101048-67-3
• 化学式: C₁₀H₅F₅O
• 分子量: 236.141
• InChiKey: QOCDZDDDUCWJFM-DUXPYHPUSA-N

物化性质

• 沸点：
  188.0±40.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-buten-2-one 、 4-磺酰胺基苯肼盐酸盐 在 4-磺酰胺基苯肼盐酸盐 作用下， 以68的产率得到1-(4-aminosulphonylphenyl)-5-(2,4-difluorophenyl)-4,5-dihydro-3-trifluoromethyl-1H-pyrazole
  参考文献：
  名称：

  Pyrazoline derivatives, their preparation and application as medicaments

  摘要：

  本发明涉及新的吡唑啉衍生物的公式和其生理上可接受的盐，以及其制备方法和作为药物的应用。

  公开号：

  US06353117B1
• 作为产物：
  描述：

  2,4-二氟苯甲醛 生成 (E)-1,1,1-trifluoro-4-(2,4-difluorophenyl)-3-buten-2-one
  参考文献：
  名称：

  Pyrazoline derivatives, their preparation and application as medicaments

  摘要：

  本发明涉及新的吡唑啉衍生物的公式和其生理上可接受的盐，以及其制备方法和作为药物的应用。

  公开号：

  US06353117B1

文献信息

• Method of preparing derivatives of 1,5-diaryl-3-trifluoromethyl-delta2-pyrazolines that are racemic and enantiomerically pure
  申请人：——

  公开号：US20040019222A1

  公开（公告）日：2004-01-29

  Procedure for preparation of compounds with the general formula 1, which include the racemic mixtures (±)-1, and the enantiomerically pure compounds (−)-1 and (+)-1, wherein R 1 and R 3 , like or different, represent an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl or methoxy group; R 2 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group; R 4 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group, with the condition that one of the substituents R 2 or R 4 is a methylsulphonyl or aminosulphonyl group; which involves obtaining the racemic mixture with the general formula (±)-1 by reacting an (E)-1,1,1-trifluoro-4-aryl-3-buten-2-one with a phenylhydrazine, followed by a treatment with chlorosulphonic acid, or by reacting with chlorosulphonic acid followed by a reaction with sodium hydroxide and, finally, with thionyl chloride. The product obtained by either of these methods is made to react with ammonium carbonate or ammonia, or with sodium sulphite and methyl iodide or methyl sulphate. In addition, to obtain the enantiomerically pure compounds with the general formula 1 by resolving the racemic mixture with the general formula (±)-1, a reaction is effected with optically active ephedrine, followed by formation of the sodium salt of each enantiomer, reaction with thionyl chloride and ammonium carbonate or ammonia, or instead with thionyl chloride followed by sodium sulphite and methyl iodide or methyl sulphate to thereby obtain separately the enantiomerically pure compounds with the general formulae (−)-1 and (+)-1. 1

  制备具有一般式1的化合物的程序，其中包括外消旋混合物(±)-1，以及对映纯化合物(−)-1和(+)-1，其中R1和R3，相同或不同，代表氢、氯、氟、甲基、三氟甲基或甲氧基原子；R2代表氢、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基、甲磺酰基或氨基磺酰基原子；R4代表氢、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基、甲磺酰基或氨基磺酰基原子，条件是R2或R4的取代基之一是甲磺酰基或氨基磺酰基；该程序包括通过将(E)-1,1,1-三氟-4-芳基-3-丁烯-2-酮与苯基肼反应，然后用氯磺酸处理，或者通过与氯磺酸反应，然后与氢氧化钠反应，最后与亚砜氯反应来获得具有一般式(±)-1的外消旋混合物。通过这两种方法得到的产物与碳酸铵或氨反应，或与亚硫酸钠和碘甲烷或硫酸甲酯反应。此外，通过与旋光活性麻黄碱反应，然后形成每个对映体的钠盐，与亚砜氯和碳酸铵或氨反应，或者与亚砜氯后跟随着亚硫酸钠和碘甲烷或硫酸甲酯来解决具有一般式(±)-1的外消旋混合物，以分别获得一般式(−)-1和(+)-1的对映纯化合物。
• Procedure for the preparation of racemic and enantiomerically pure derivatives O F 1,5 diaryl-3-trifluorromethyl-delta2-pyrazolines
  申请人：Alcon-Marrugat Montserrat

  公开号：US20050096373A1

  公开（公告）日：2005-05-05

  Procedure for preparation of compounds with the general formula 1, which include the racemic mixtures (±)-1, and the enantiomerically pure compounds (−)-1 and (+)-1, wherein R 1 and R 3 , like or different, represent an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl or methoxy group; R 2 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group; R 4 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group, with the condition that one of the substituents R 2 or R 4 is a methylsulphonyl or aminosulphonyl group; which involves obtaining the racemic mixture with the general formula (±)-1 by reacting an (E)-1,1,1-trifluoro-4-aryl-3-buten-2-one with a phenylhydrazine, followed by a treatment with chlorosulphonic acid, or by reacting with chlorosulphonic acid followed by a reaction with sodium hydroxide and, finally, with thionyl chloride. The product obtained by either of these methods is made to react with ammonium carbonate or ammonia, or with sodium sulphite and methyl iodide or methyl sulphate. In addition, to obtain the enantiomerically pure compounds with the general formula 1 by resolving the racemic mixture with the general formula (±)-1, a reaction is effected with optically active ephedrine, followed by formation of the sodium salt of each enantiomer, reaction with thionyl chloride and ammonium carbonate or ammonia, or instead with thionyl chloride followed by sodium sulphite and methyl iodide or methyl sulphate to thereby obtain separately the enantiomerically pure compounds with the general formulae (−)-1 and (+)-1.

  制备通式为1的化合物的程序，其中包括外消旋混合物（±）-1和对映纯化合物（-）-1和（+）-1，其中R1和R3，相同或不同，代表氢、氯、氟、甲基、三氟甲基或甲氧基原子；R2代表氢、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基、甲基磺酰基或氨基磺酰基原子；R4代表氢、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基、甲基磺酰基或氨基磺酰基原子，其中R2或R4的取代基之一为甲基磺酰基或氨基磺酰基；该程序包括通过将（E）-1,1,1-三氟-4-芳基-3-丁烯-2-酮与苯肼反应，然后用氯磺酸处理，或与氯磺酸反应，然后与氢氧化钠和亚磺酰氯反应，从而获得通式为（±）-1的外消旋混合物。通过这些方法得到的产物与碳酸铵或氨或亚硫酸钠和碘甲烷或甲磺酸甲酯反应。此外，通过用旋光性麻黄碱分离通式为（±）-1的外消旋混合物，随后形成每个对映体的钠盐，然后与亚磺酰氯和碳酸铵或氨反应，或者用亚磺酰氯后接着用亚硫酸钠和碘甲烷或甲磺酸甲酯，从而分别获得对映纯化合物（-）-1和（+）-1。
• Procedure for the preparation of racemic and enantiomerically pure derivatives of 1,5 diaryl-3-trifluorromethyl-Δ2-pyrazolines
  申请人：Alcon-Marrugat Montserrat

  公开号：US06958403B2

  公开（公告）日：2005-10-25

  Procedure for preparation of compounds with the general formula 1, which include the racemic mixtures (±)-1, and the enantiomerically pure compounds (−)-1 and (+)-1, wherein R 1 and R 3 , like or different, represent an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl or methoxy group; R 2 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group; R 4 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group, with the condition that one of the substituents R 2 or R 4 is a methylsulphonyl or aminosulphonyl group; which involves obtaining the racemic mixture with the general formula (±)-1 by reacting an (E)-1,1,1-trifluoro-4-aryl-3-buten-2-one with a phenylhydrazine, followed by a treatment with chlorosulphonic acid, or by reacting with chlorosulphonic acid followed by a reaction with sodium hydroxide and, finally, with thionyl chloride. The product obtained by either of these methods is made to react with ammonium carbonate or ammonia, or with sodium sulphite and methyl iodide or methyl sulphate. In addition, to obtain the enantiomerically pure compounds with the general formula 1 by resolving the racemic mixture with the general formula (±)-1, a reaction is effected with optically active ephedrine, followed by formation of the sodium salt of each enantiomer, reaction with thionyl chloride and ammonium carbonate or ammonia, or instead with thionyl chloride followed by sodium sulphite and methyl iodide or methyl sulphate to thereby obtain separately the enantiomerically pure compounds with the general formulae (−)-1 and (±)-1.

  制备通式为1的化合物的程序，包括混合物(±)-1和对映纯化合物(−)-1和(+)-1，其中R1和R3，相同或不同，代表氢原子、氯、氟、甲基、三氟甲基或甲氧基基团；R2代表氢原子、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基、甲磺酰基或氨基磺酰基基团；R4代表氢原子、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基、甲磺酰基或氨基磺酰基基团，其中R2或R4中的一个基团是甲磺酰基或氨基磺酰基；通过将(E)-1,1,1-三氟-4-芳基-3-丁烯-2-酮与苯肼反应，然后经氯磺酸处理，或通过与氯磺酸反应，然后与氢氧化钠反应，最后与亚磺酰氯反应，制备通式为(±)-1的混合物。然后将通过任何一种方法得到的产物与碳酸铵或氨，或与亚硫酸钠和碘甲烷或甲磺酸甲酯反应。此外，通过与光学活性麻黄碱反应，形成每个对映体的钠盐，然后与亚磺酰氯和碳酸铵或氨反应，或者与亚磺酰氯后跟随着亚硫酸钠和碘甲烷或甲磺酸甲酯反应，分别获得对映纯化合物(−)-1和(±)-1。
• PYRAZOLINE DERIVATIVES, THEIR PREPARATION AND APPLICATION AS MEDICAMENTS
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP1083171A1

  公开（公告）日：2001-03-14

  The present invention relates to new pyrazoline derivatives having the general formula (I), as well as to their physiologically acceptable salts, to process in human/veterinary therapy and to pharmaceutical compositions containing them. The new compounds of the invention can be used in the pharmaceutical industry as intermediates and for the preparation of medicaments. In particular, they can be used for the preparation of medicaments used for the treatment of inflammation and other troubles associated to inflammation and other process mediated by cyclooxygenase-2, for example arthritis, pain treatment or fever treatment.

  本发明涉及具有通式（I）的新吡唑啉衍生物及其生理上可接受的盐类、人类/兽医治疗过程以及含有它们的药物组合物。本发明的新化合物可作为中间体用于制药业和制备药物。特别是，它们可用于制备治疗炎症和与炎症有关的其他问题以及环氧化酶-2 介导的其他过程的药物，例如关节炎、疼痛治疗或发烧治疗。
• Use of pyrazoline derivatives in the preparation of a medicament for the prevention and/or treatment of cell proliferation diseases
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP1516621A2

  公开（公告）日：2005-03-23

  Derivatives of pyrazoline (I), wherein R1 is hydrogen, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, carboxylic acid, alkyl carboxylate with 1 to 4 carbon atoms, carboxamide or cyano, R2 is hydrogen or methyl, R3, R4, R7 and R8, independently are hydrogen, chlorine, fluorine, methyl, trifluoromethyl or methoxy, R5 and R6, independently, are hydrogen, chlorine, fluorine, methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl, aminosulphonyl or acetylaminosulphonyl, with the condition that one of the substituents R5 or R6 is a methylsulphonyl, aminosulphonyl or acetylaminosulphonyl group, and with the condition that when R1 is methyl, then R2 is hydrogen or methyl, R3 and R8, independently are hydrogen, chlorine, fluorine, methyl, or trifluoromethyl, R4 is hydrogen, , fluorine, methyl, trifluoromethyl or methoxy, R5 is fluorine, trifluoromethyl, trifluoromethoxy, methylsulphonyl, aminosulphonyl or acetylaminosulphonyl, R6 is hydrogen, chlorine, fluorine, methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl, aminosulphonyl or acetylaminosulphonyl, with the condition that one of the substituents R5 or R6 is a methylsulphonyl, aminosulphonyl or acetylaminosulphonyl group, and R7 represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl or methoxy group; useful for preventing or treating cell proliferation diseases.

  吡唑啉的衍生物(I)，其中 R1 是氢、甲基、氟甲基、二氟甲基、三氟甲基、羧酸、含 1 至 4 个碳原子的烷基羧酸酯、羧酰胺或氰基；R2 是氢或甲基；R3、R4、R7 和 R8 独立地是氢、氯、氟、甲基、三氟甲基或甲氧基；R5 和 R6、独立地为氢、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基、甲基磺酰基、氨基磺酰基或乙酰氨基磺酰基，条件是取代基 R5 或 R6 之一为甲基磺酰基、氨基磺酰基或乙酰氨基磺酰基，条件是当 R1 为甲基时，则 R2 为氢或甲基，R3、R4、R7 和 R8 独立地为氢、氯、氟、甲基、三氟甲基或甲氧基，R5 和 R6 独立地为氢、氯、氟、甲基、三氟甲基、甲氧基、三氟甲氧基或乙酰氨基磺酰基、则 R2 为氢或甲基，R3 和 R8 分别为氢、氯、氟、甲基或三氟甲基，R4 为氢、氟、甲基、三氟甲基或甲氧基，R5 为氟、三氟甲基、三氟甲氧基、甲磺酰基、氨磺酰基或乙酰氨基磺酰基，R6 为氢、氯、氟、甲基、三氟甲基、甲氧基或乙酰氨基磺酰基、R5或R6中的一个取代基是甲基磺酰基、氨磺酰基或乙酰氨基磺酰基，R7代表氢原子、氯原子、氟原子、甲基、三氟甲基或甲氧基；可用于预防或治疗细胞增殖疾病。