4-(4-氯苯基)-1-[3-[2-(4-氟苯基)-1,3-二氧戊环-2-基]丙基]哌啶-4-醇 | 56660-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(4-氯苯基)-1-[3-[2-(4-氟苯基)-1,3-二氧戊环-2-基]丙基]哌啶-4-醇
• 英文名称: 4-<4-(4-chlorophenyl)-4-hydroxypiperidino>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane
• 英文别名: 4-[4-(4-chlorophenyl)-4-hydroxypiperidino]-1,1-ethylenedioxy-1-(4-fluorophenyl)butane；<14C>-Haloperidol-ethylenketal；[14C]-Haloperidol-ethylenketal；4-Piperidinol, 4-(p-chlorophenyl)-1-(3-(2-(p-fluorophenyl)-1,3-dioxolan-2-yl)propyl)-；4-(4-chlorophenyl)-1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-ol
• CAS: 56660-99-2
• 化学式: C₂₃H₂₇ClFNO₃
• 分子量: 419.924
• InChiKey: BUJLOFQXOPFTPX-UHFFFAOYSA-N

物化性质

• 沸点：
  549.1±50.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-氯苯基)-1-[3-[2-(4-氟苯基)-1,3-二氧戊环-2-基]丙基]哌啶-4-醇 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以65%的产率得到氟哌啶醇
  参考文献：
  名称：

  室温离子液体中的Stetter反应及其在氟哌啶醇合成中的应用

  摘要：

  咪唑型室温离子液体（RTIL）已用于Stetter反应，以良好的收率提供了所需的1,4-二羰基化合物。噻唑鎓盐和Et 3 N是在离子液体中进行该反应的有效催化剂。已经证明了再循环和再利用溶剂的可能性，尽管不可能再循环噻唑鎓催化剂。该方法用于氟哌啶醇的全合成。

  DOI：

  10.1002/adsc.200404123
• 作为产物：
  描述：

  4-氯-4'-氟苯丁酮 在 potassium carbonate 、 对甲苯磺酸 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 29.5h， 生成 4-(4-氯苯基)-1-[3-[2-(4-氟苯基)-1,3-二氧戊环-2-基]丙基]哌啶-4-醇
  参考文献：
  名称：

  Synthesis of high specific activity [75Br]- and [77Br]bromperidol and tissue distribution studies in the rat

  摘要：

  A rapid synthesis of [75Br]- and [77Br]bromperidol with specific activity exceeding 10000 Ci/mmol is described in which a trimethylstannylated analogue of bromperidol is used as a substrate for regiospecific no-carrier-added radiobromination. 4-[4-[4-(Trimethylstannyl)phenyl]-4-hydroxypiperidino]-4'- fluorobutyrophenone was synthesized by the reaction of (trimethylstannyl)sodium with haloperidol and purified by preparative HPLC. Subsequent radiobromination with no-carrier-added 75Br- or 77Br- and in situ oxidation using H2O2/CH3COOH gave a corrected radiochemical yield of 35% with a 30-min preparation time. Tissue distribution studies in the rat show a rapid and prolonged uptake into the brain, liver, and kidneys and consistently low blood concentrations that differ quantitatively from previous studies using relatively low specific activity bromperidol. Potential clinical applications for this high specific activity radiobrominated neuroleptic are discussed.

  DOI：

  10.1021/jm00147a035

文献信息

• FELLOWS I.; HARROW T. A.; HONEYMAN R., J. LABELLED COMPOUNDS AND RADIOPHARM., 1979, 16, NO 3, 449-461
  作者：FELLOWS I.、 HARROW T. A.、 HONEYMAN R.

  DOI：——

  日期：——
• XASEHGAVA, GEHN;TSUDA, SADANAO;ARITA, MASABUMI;KAVA, TOSINOBU
  作者：XASEHGAVA, GEHN、TSUDA, SADANAO、ARITA, MASABUMI、KAVA, TOSINOBU

  DOI：——

  日期：——
• Stetter Reaction in Room Temperature Ionic Liquids and Application to the Synthesis of Haloperidol
  作者：Siddam Anjaiah、Srivari Chandrasekhar、René Grée

  DOI：10.1002/adsc.200404123

  日期：2004.9

  Imidazolium-type room temperature ionic liquids (RTILs) have been used for the Stetter reaction, affording the desired 1,4-dicarbonyl compounds in good yields. Thiazolium salts and Et3N are efficient catalysts for this reaction performed in ionic liquid. The possibility to recycle and reuse the solvent has been demonstrated, although it was not possible to recycle the thiazolium catalyst. This method

  咪唑型室温离子液体（RTIL）已用于Stetter反应，以良好的收率提供了所需的1,4-二羰基化合物。噻唑鎓盐和Et 3 N是在离子液体中进行该反应的有效催化剂。已经证明了再循环和再利用溶剂的可能性，尽管不可能再循环噻唑鎓催化剂。该方法用于氟哌啶醇的全合成。
• Synthesis of high specific activity [75Br]- and [77Br]bromperidol and tissue distribution studies in the rat
  作者：Stephen M. Moerlein、Gerhard L. Stoecklin

  DOI：10.1021/jm00147a035

  日期：1985.9

  A rapid synthesis of [75Br]- and [77Br]bromperidol with specific activity exceeding 10000 Ci/mmol is described in which a trimethylstannylated analogue of bromperidol is used as a substrate for regiospecific no-carrier-added radiobromination. 4-[4-[4-(Trimethylstannyl)phenyl]-4-hydroxypiperidino]-4'- fluorobutyrophenone was synthesized by the reaction of (trimethylstannyl)sodium with haloperidol and purified by preparative HPLC. Subsequent radiobromination with no-carrier-added 75Br- or 77Br- and in situ oxidation using H2O2/CH3COOH gave a corrected radiochemical yield of 35% with a 30-min preparation time. Tissue distribution studies in the rat show a rapid and prolonged uptake into the brain, liver, and kidneys and consistently low blood concentrations that differ quantitatively from previous studies using relatively low specific activity bromperidol. Potential clinical applications for this high specific activity radiobrominated neuroleptic are discussed.