2-(4-氟苯基)-1-吡唑烷-1-基乙酮 | 702695-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-氟苯基)-1-吡唑烷-1-基乙酮
• 英文名称: 2-(4-fluorophenyl)-1-(1-pyrazolidin-1-yl)ethanone
• 英文别名: 2-(4-fluorophenyl)-1-pyrazolidin-1-ylethanone；1-[(4-fluorophenyl)acetyl]pyrazolidine；1-(4-fluorophenylacetyl)pyrazolidine；2-(4-Fluorophenyl)-1-(pyrazolidin-1-yl)ethan-1-one
• CAS: 702695-15-6
• 化学式: C₁₁H₁₃FN₂O
• 分子量: 208.235
• InChiKey: JLFFOQNXBKRRIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-氟苯基)-1-吡唑烷-1-基乙酮 在 Oxone 、 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 2-(4-fluorophenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one
  参考文献：
  名称：

  Development of Orally Bioavailable Bicyclic Pyrazolones as Inhibitors of Tumor Necrosis Factor-α Production

  摘要：

  2-Aryl-3-pyrimidinyl based tumor necrosis factor-alpha (TNF-alpha) inhibitors, which contain a novel bicyclic pyrazolope core, are described. Many showed low-nanomolar activity against lipopolysaccharide-induced TNF-alpha production in monocytic cells. Secondary screening data are presented for the pyrimidinyl bicyclic pyrazolones. Several of these analogues showed good oral bioavailability in rat and efficacy in the rat iodoacetate in vivo model.

  DOI：

  10.1021/jm049968m
• 作为产物：
  描述：

  对氟苯乙酰氯 在 盐酸 、 吡啶硼烷 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.5h， 生成 2-(4-氟苯基)-1-吡唑烷-1-基乙酮
  参考文献：
  名称：

  Facile Scalable Reduction of N-Acylated Dihydropyrazoles

  摘要：

  The reduction of a variety of highly functionalized N-acylated dihydropyrazoles (1) with BH3, pyridine is described. The process through which this unexpectedly difficult reduction was discovered and developed is reported. A facile atom-efficient route to the N-acylated dihydropyrazole reduction precursors (1) is also illustrated. The resulting acylpyrazolidine products (2) that arise upon reduction were isolated in good to high yields following exposure to reaction conditions which have been shown to tolerate a variety of different functional groups. Finally, this route has been demonstrated on a kilogram scale and provides direct access to potential proline surrogates for peptidomimetic applications.

  DOI：

  10.1021/jo060567j

文献信息

• Synthesis of 1-mono- and 1,2-bisacylpyrazolidines and 1-arylsulfonylpyrazolines
  作者：V. Yu. Petukhova、V. A. Maslennikov、V. V. Kuznetsov、N. N. Makhova、S. A. Serkov

  DOI：10.1007/s11172-010-0257-2

  日期：2010.7

  Study of a reaction of 1,5-diazabicyclo[3.1.0]hexanes with acyl and sulfonyl chlorides in organic or aqueous organic media in the presence of inorganic bases resulted in development of new simple one-step methods for the preparation of 1-mono- and 1,2-bisacylpyrazolidines and 1-arylsulfonylpyrazolines.

  通过对 1,5-二氮杂双环[3.1.0]己烷与酰基和磺酰基氯在有机或含水有机介质中在无机碱存在下的反应的研究，开发出了一步法制备 1-单酰基和 1,2-双酰基吡唑烷和 1-芳基磺酰基吡唑烷的新的简单方法。
• Ring transformation of 1,5-diazabicyclo[3.1.0]hexanes under the action of arylketenes
  作者：Alexander V. Shevtsov、Vladimir V. Kuznetsov、Alexander A. Kislukhin、Vera Yu. Petukhova、Yu. A. Strelenko、Nina N. Makhova、Konstantin A. Lyssenko

  DOI：10.1002/jhet.5570430411

  日期：2006.7

  instead of the expected bicyclic systems 1,5-diazabicyclo[3.2.1]octan-6-one 9 and 3-aryl-1,5-diazabicyclo[3.3.0]octane-2-one 10. The synthesis of two representatives of bicycles 10 (10a,b) proceeded in the reaction of unsubstituted 1,5-diazabicycle[3.1.0]hexane 8a, accordingly, with diphenylketene 1a in benzene at 20 °C and with 4-chlorophenylketene 1b in toluene at 60-110 °C. Mechanisms of the studied transformations

  1,5-二氮杂双环[3.1.0]己烷8与芳基烯酮1的反应已在不同条件下进行了研究。1-（芳基乙基）吡唑烷11是在-30°C的乙醚中和20°C的苯中获得的，而不是预期的双环体系1,5-二氮杂双环[3.2.1] octan-6-one 9和3-芳基-1,5-二氮杂双环[3.3.0]辛烷-2-一10。自行车10（10a，b）的两个代表的合成在未取代的1，5-二氮杂双环[3.1.0]己烷8a的反应中进行，相应地，在20℃下与苯中的二苯基乙烯酮1a和4-氯苯基乙烯酮1b反应。在60-110°C的甲苯中溶解。提供了研究的转化机制。
• New simple synthesis of N-acylpyrazolidines and N-arylsulfonyl-2-pyrazolines
  作者：Alexander V. Shevtsov、Alexander A. Kislukhin、Vladimir V. Kuznetsov、Vera Yu. Petukhova、Vladimir A. Maslennikov、Alexandra O. Borissova、Konstantin A. Lyssenko、Nina N. Makhova

  DOI：10.1016/j.mencom.2007.03.023

  日期：2007.3

  New simple methods for the synthesis of 1-mono- and 1,2-diacylpyrazolidines as well as 1-arylsulfonyl-2-pyrazolines, based on the interaction of 1,5-diazabicylo[3.1.0]hexanes with acyl- or arylsulfonyl chlorides, have been proposed.
• Convergent synthesis of 2,3-bisarylpyrazolones through cyclization of bisacylated pyrazolidines and hydrazines
  作者：Todd A. Brugel、Tomas Hudlicky、Michael P. Clark、Adam Golebiowski、Mark Sabat、Mary Ann A. Endoma、Vu Bui、David Adams、Matthew J. Laufersweiler、Jennifer A. Maier、Roger G. Bookland、Biswanath De

  DOI：10.1016/j.tetlet.2006.03.063

  日期：2006.5

  Cyclization of various bisacylated hydrazines and pyrazolidines using DBU or sodium hydride leads to the formation of various mono-, bi- and tricyclic pyrazolone scaffolds in 41-98% yield. The convergent nature by which the precyclization intermediates are constructed allows for rapid derivatization about the pyrazolone core. (c) 2006 Elsevier Ltd. All rights reserved.
• Facile Scalable Reduction of <i>N</i>-Acylated Dihydropyrazoles
  作者：Michael D. Curtis、Nancy C. Hayes、Patricia A. Matson

  DOI：10.1021/jo060567j

  日期：2006.6.1

  The reduction of a variety of highly functionalized N-acylated dihydropyrazoles (1) with BH3, pyridine is described. The process through which this unexpectedly difficult reduction was discovered and developed is reported. A facile atom-efficient route to the N-acylated dihydropyrazole reduction precursors (1) is also illustrated. The resulting acylpyrazolidine products (2) that arise upon reduction were isolated in good to high yields following exposure to reaction conditions which have been shown to tolerate a variety of different functional groups. Finally, this route has been demonstrated on a kilogram scale and provides direct access to potential proline surrogates for peptidomimetic applications.