(4-Pentylphenyl)hydrazine | 849095-10-9

• 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: (4-Pentylphenyl)hydrazine
• CAS: 849095-10-9
• 化学式: C₁₁H₁₈N₂
• 分子量: 178.277
• InChiKey: NQXRBSHZHVXZSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-Pentylphenyl)hydrazine 在 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成 5-Chloro-4-(4-methoxyphenoxy)-2-(4-pentylphenyl)pyridazin-3-one
  参考文献：
  名称：

  Design, synthesis and SAR analysis of novel potent and selective small molecule antagonists of NPBWR1 (GPR7)

  摘要：

  Novel smallmolecule antagonists ofNPBWR1 (GPR7) are herein reported. A high-throughput screening (HTS) of the Molecular Libraries-Small Molecule Repository library identified 5-chloro-4-(4-methoxyphenoxy)-2-(p-tolyl)pyridazin-3(2H)-one as a NPBWR1 hit antagonist with micromolar activity. Design, synthesis and structure-activity relationships study of the HTS-derived hit led to the identification of 5-chloro-2-(3,5-dimethylphenyl)-4-(4-methoxyphenoxy) pyridazin-3(2H)-one lead molecule with sub-micromolar antagonist activity at the target receptor and high selectivity against a panel of therapeutically relevant off-target proteins. This lead molecule may provide a pharmacological tool to clarify the molecular basis of the in vivo physiological function and therapeutic utility of NPBWR1 in diverse disease areas including inflammatory pain and eating disorders. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.074

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 derivatives of 1,5-diaryl-3-trifluoromethyl-delta2-pyrazolines
  申请人：Alcon-Marrugat Monserrat

  公开号：US20050096474A1

  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.

  通式 1 化合物的制备步骤，包括外消旋混合物 (±)-1 和对映体纯化合物 (-)-1 和 (+)-1，其中 R 1 和 R 3 代表氢原子、氯原子、氟原子、甲基、三氟甲基或甲氧基；R 2 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的原子； R 4 4 代表氢原子、氯原子、氟原子、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，条件是其中一个取代基 R 2 或 R 4 是甲磺酰基或氨磺酰基；其方法是将(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，然后与氢氧化钠反应，最后与亚硫酰氯反应，得到通式为(±)-1的外消旋混合物。通过上述任一方法得到的产品都会与碳酸铵或氨反应，或与亚硫酸钠和碘甲烷或硫酸甲酯反应。此外，为了通过解析通式（±）-1 的外消旋混合物来获得通式 1 的对映体纯化合物，需要与具有光学活性的麻黄碱进行反应，然后生成每种对映体的钠盐、与亚硫酰氯和碳酸铵或氨反应，或先与亚硫酰氯反应，再与亚硫酸钠和碘甲烷或硫酸甲酯反应，从而分别获得通式为 (-)-1 和 (+)-1 的对映体纯化合物。
• NEFEDOV V. A.; GERMAN N. A.; LUTSENKO A. I.; NIKISHIN G. I., ZH. ORGAN. XIMII, 23,(1987) N 1, 172-181
  作者：NEFEDOV V. A.、 GERMAN N. A.、 LUTSENKO A. I.、 NIKISHIN G. I.

  DOI：——

  日期：——
• METHOD OF PREPARING DERIVATIVES OF 1.5-DIARYL-3-TRIFLUOROMETHYL-DELTA2-PYRAZOLINES THAT ARE RACEMIC AND ENANTIOMERICALLY PURE
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP1408035B1

  公开（公告）日：2006-01-04