1,1,1-trifluoro-4-nitrobutane | 32827-23-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1,1,1-trifluoro-4-nitrobutane
• 英文别名: 1-Nitro-4,4,4-trifluorobutan
• CAS: 32827-23-9
• 化学式: C₄H₆F₃NO₂
• 分子量: 157.092
• InChiKey: HWSQUNJZNMYSDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-4-nitrobutane 、 3-(benzyloxy)-5-ethynylpyridine 在 异氰酸苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 以72%的产率得到3-(benzyloxy)-5-[3-(3,3,3-trifluoropropyl)-5-isoxazolyl]pyridine
  参考文献：
  名称：

  Discovery of Highly Potent and Selective α4β2-Nicotinic Acetylcholine Receptor (nAChR) Partial Agonists Containing an Isoxazolylpyridine Ether Scaffold that Demonstrate Antidepressant-like Activity. Part II

  摘要：

  In our continued efforts to develop alpha 4 beta 2-nicotinic acetylcholine receptor (nAChR) partial agonists as novel antidepressants having a unique mechanism of action, structure-activity relationship (SAR) exploration of certam isoxazolylpyridine ethers is presented. In particular, modifications to both the azetidine ring present in the starting structure 4 and its metabolically liable hydroxyl side chain substituent have been explored to improve compound druggability. The pharmacological characterization of all new compounds has been carried out using [H-3]epibatidine binding studies together with functional assays based on Rb-86(+) ion flux measurements. We found that the deletion of the metabolically liable hydroxyl group or its replacement by a fluoromethyl group not only maintained potency and selectivity but also resulted in compounds showing antidepressant-like properties in the mouse forced swim test. These isoxazolylpyridine ethers appear to represent lead candidates in the design of innovative chemical tools containing reporter groups for imaging purposes and of possible therapeutics.

  DOI：

  10.1021/jm301177j
• 作为产物：
  描述：

  4,4,4-三氟-1-碘丁烷 在 silver(I) nitrite 作用下， 以 乙醚 为溶剂， 反应 50.25h， 生成 1,1,1-trifluoro-4-nitrobutane
  参考文献：
  名称：

  [EN] CYCLOBUTENEDIONE GROUPS-CONTAINING COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
  [FR] GROUPES CYCLOBUTENEDIONE CONTENANT DES COMPOSES SERVANT D'INHIBITEURS A LA SERINE PROTEASE NS3 DU VIRUS DE L'HEPATITE C

  摘要：

  本发明公开了具有HCV蛋白酶抑制活性的新化合物，以及制备这种化合物的方法。在另一实施方式中，本发明公开了包含这种化合物的药物组合物，以及使用它们治疗与HCV蛋白酶相关的疾病的方法。

  公开号：

  WO2005085197A1

文献信息

• [EN] CYCLOBUTENEDIONE GROUPS-CONTAINING COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE<br/>[FR] GROUPES CYCLOBUTENEDIONE CONTENANT DES COMPOSES SERVANT D'INHIBITEURS A LA SERINE PROTEASE NS3 DU VIRUS DE L'HEPATITE C
  申请人：SCHERING CORP

  公开号：WO2005085197A1

  公开（公告）日：2005-09-15

  The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

  本发明公开了具有HCV蛋白酶抑制活性的新化合物，以及制备这种化合物的方法。在另一实施方式中，本发明公开了包含这种化合物的药物组合物，以及使用它们治疗与HCV蛋白酶相关的疾病的方法。
• Fluorine-containing nitrogen compounds—VI
  作者：E.R. Bissell、D.B. Fields

  DOI：10.1016/0040-4020(70)80010-2

  日期：——

  Sulfur tetrafluoride converts aliphatic nitro acids to the corresponding trifluoromethyl compounds. The yield is poor with primary nitro acids; but high yields of fluoronitrocarbons, otherwise difficult to obtain, are produced from certain γ-substituted butyric acids and from substituted acrylic acids. Eleven new fluoronitrocarbons are described.

  四氟化硫将脂肪族硝基酸转化为相应的三氟甲基化合物。伯硝酸的收率很低。但是由某些γ-取代的丁酸和取代的丙烯酸可制得高产率的氟代硝基碳，否则很难获得。描述了十一种新的氟代硝基碳。
• [EN] NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE<br/>[FR] NOUVEAUX COMPOSES EN TANT QU'INHIBITEURS DE LA SERINE PROTEASE NS3 DU VIRUS DE L'HEPATITE C
  申请人：SCHERING CORP

  公开号：WO2005087725A3

  公开（公告）日：2005-10-27
• [EN] COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE<br/>[FR] NOUVEAUX COMPOSES EN TANT QU'INHIBITEURS DE LA PROTEASE SERINE NS3 DU VIRUS DE L'HEPATITE C
  申请人：SCHERING CORP

  公开号：WO2005087721A3

  公开（公告）日：2005-11-10
• Discovery of SCH446211 (SCH6):  A New Ketoamide Inhibitor of the HCV NS3 Serine Protease and HCV Subgenomic RNA Replication
  作者：Stéphane L. Bogen、Ashok Arasappan、Frank Bennett、Kevin Chen、Edwin Jao、Yi-Tsung Liu、Raymond G. Lovey、Srikanth Venkatraman、Weidong Pan、Tajel Parekh、Russel E. Pike、Sumei Ruan、Rong Liu、Bahige Baroudy、Sony Agrawal、Robert Chase、Paul Ingravallo、John Pichardo、Andrew Prongay、Jean-Marc Brisson、Tony Y. Hsieh、Kuo-Chi Cheng、Scott J. Kemp、Odile E. Levy、Marguerita Lim-Wilby、Susan Y. Tamura、Anil K. Saksena、Viyyoor Girijavallabhan、F. George Njoroge

  DOI：10.1021/jm060077j

  日期：2006.5.1

  Introduction of various modified prolines at P-2 and optimization of the P-1 side chain led to the discovery of SCH6 (24, Table 2), a potent ketoamide inhibitor of the HCV NS3 serine protease. In addition to excellent enzyme potency (K-i* = 3.8 nM), 24 was also found to be a potent inhibitor of HCV subgenomic RNA replication with IC50 and IC90 of 40 and 100 nM, respectively. Recently, antiviral activity of 24 was demonstrated with inhibition of the full-length genotype 2a HCV genome. In addition, 24 was found to restore the responsiveness of the interferon regulatory factor 3 (IRF-3) in cells containing HCV RNA replicons.