3-硝基三氟苯乙酮肟 | 220493-46-9

• 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: 3-硝基三氟苯乙酮肟
• 英文名称: 2,2,2-trifluoro-1-(3-nitrophenyl)ethan-1-one oxime
• 英文别名: 2,2,2-Trifluoro-1-(3-nitrophenyl)ethanone oxime；N-[2,2,2-trifluoro-1-(3-nitrophenyl)ethylidene]hydroxylamine
• CAS: 220493-46-9
• 化学式: C₈H₅F₃N₂O₃
• 分子量: 234.135
• InChiKey: VATVDZRYXNKLKC-UHFFFAOYSA-N

物化性质

• 熔点：
  48-51 °C
• 沸点：
  278.8±40.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-硝基三氟苯乙酮肟 在 4-二甲氨基吡啶 、 sodium dithionite 、 氨 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 重水 为溶剂， 反应 58.0h， 生成 3-(3-(trifluoromethyl)-3H-diazirin-3-yl)aniline
  参考文献：
  名称：

  NLRP3抑制剂重氮嗪光亲和探针的设计，合成和评估

  摘要：

  NLRP3抑制剂MCC950 / CRID3可改善动物模型中的大量炎症性疾病。在本文中，我们描述了一种称为TPD-950-Br的三氟甲基苯基重氮（TPD）光亲和探针，以探测MCC950的分子相互作用。我们显示，TPD-950-Br在NLRP3抑制剂检测中共激活并在光活化后捕获近端物质，并抑制IL-1β的产生。

  DOI：

  10.1016/j.tetlet.2020.151849
• 作为产物：
  描述：

  3-硝基-2,2,2-三氟苯乙酮 在 吡啶 、 盐酸羟胺 作用下， 反应 1.0h， 生成 3-硝基三氟苯乙酮肟
  参考文献：
  名称：

  从甲苯磺酰肟衍生物的另一种一锅法合成（三氟甲基）苯基重氮嗪：在光学亲和标记中用于光学纯二叠氮基苯基丙氨酸的新合成方法的应用

  摘要：

  开发了由相应的甲苯磺肟肟形成的另一种一锅法合成3-（三氟甲基）-3-苯基重氮基衍生物。中间diaziridine的由NH去质子化2 -是用于施工二吖丙因的新方法。而且，尝试了涉及这些方法的光学纯的（三氟甲基）二氮杂基苯基丙氨酸衍生物的新型合成。

  DOI：

  10.1021/ol503630z

文献信息

• Cinnamide derivatives as KCNQ potassium channel modulators
  申请人：——

  公开号：US20030166650A1

  公开（公告）日：2003-09-04

  There is provided novel cinnamide derivatives of Formula I 1 wherein R is C 1-4 alkyl or trifluoromethyl; R 1 is selected from the group consisting of pyridinyl, quinolinyl, thienyl, furanyl, 1,4-benzodioxanyl, 1,3-benzodioxolyl, chromanyl, indanyl, biphenylyl, phenyl and substituted phenyl in which said substituted phenyl is substituted with one or two substituents each independently selected-from the group consisting of halogen, C 1-4 alkyl, C 1-4 alkoxy, trifluoromethyl, trifluoromethoxy and nitro; R 2 and R 3 are each independently selected from the group consisting of hydrogen, C 1-4 alkyl, and halogen; R 4 is selected from the group consisting of di(C 1-4 alkyl)amino, trifluoromethoxy and optionally substituted morpholin-4-yl, pyridinyl, pyrimidinyl, piperazinyl, and pyrazinyl with one or two substituents in which said substituent is independently selected from the group consisting of C 1-4 alkyl, aminomethyl, hydroxymethyl, chloro or fluoro; R 5 is hydrogen, chloro or fluoro; or R 4 and R 5 taken together are —CH═CH—CH═CH— or —X(CH 2 ) m Y— in which X and Y are each independently selected from the group consisting of CH 2 , (CH 2 ) n N(R 9 )— and O, wherein m is 1 or 2; n is 0 or 1; and R 6 , R 7 , and R 8 are each independently selected from hydrogen, chloro and fluoro; and R 9 is selected from the group consisting of hydrogen, C 1-4 alkyl, hydroxyethyl, C 1-4 alkoxyethyl, cyclopropylmethyl, —CO 2 (C 1-4 alkyl), and —CH 2 CH 2 NR 10 R 11 in which R 10 and R 11 are each independently hydrogen or C 1-4 alkyl, which are openers of the KCNQ potassium channels and are useful in the treatment of disorders which are responsive to the opening of the KCNQ potassium channels.

  提供了一种新型的苯甲酰胺衍生物，其化学式为I1，其中R为C1-4烷基或三氟甲基；R1选自吡啶基，喹啉基，噻吩基，呋喃基，1,4-苯并二氧杂环基，1,3-苯并二氧杂环基，色环基，茚基，联苯基，苯基和取代苯基，其中所述取代苯基被一个或两个取代基取代，每个取代基独立地选自卤素，C1-4烷基，C1-4烷氧基，三氟甲基，三氟甲氧基和硝基；R2和R3各自选自氢，C1-4烷基和卤素；R4选自二(C1-4烷基)氨基，三氟甲氧基和可选取代的吗啉-4-基，吡啶基，嘧啶基，哌嗪基和吡嗪基，其中所述取代基独立地选自C1-4烷基，氨甲基，羟甲基，氯或氟；R5为氢，氯或氟；或R4和R5共同为—CH═CH—CH═CH—或—X(CH2)mY—，其中X和Y各自独立地选自 ，( )nN(R9)—和O，其中m为1或2；n为0或1；R6、R7和R8各自选自氢，氯和氟；R9选自氢，C1-4烷基，羟乙基，C1-4烷氧乙基，环丙基甲基，—CO2(C1-4烷基)和— NR10R11，其中R10和R11各自独立地选自氢或C1-4烷基，这些化合物是KCNQ钾通道的开放剂，可用于治疗对KCNQ钾通道开放有反应的疾病。
• [EN] SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME<br/>[FR] SULFONYLURÉES, COMPOSÉS APPARENTÉS, ET LEUR UTILISATION
  申请人：UNIV QUEENSLAND

  公开号：WO2016131098A8

  公开（公告）日：2017-03-16
• Structurally similar small molecule photoaffinity CCK-A agonists and antagonists as novel tools for directly probing 7TM receptor-ligand interactions
  作者：James W. Darrow、Elizabeth M. Hadac、Laurence J. Miller、Elizabeth E. Sugg

  DOI：10.1016/s0960-894x(98)00548-4

  日期：1998.11

  Incorporation of photolabile benzoyl (2a-d) or trifluoromethyl-3H-diazirine (3a-d) substituents into 1,5-benzodiazepine ligands did not significantly impair the rat CCK-A binding affinity of either agonists or antagonists. The modified agonist ligands also retained functional potency and efficacy in the rat amylase assay. Despite their strong structural similarity, the SAR of this limited set of compounds suggests that these small molecule antagonists and agonists might differ in their mode of binding to the CCK-A receptor. Preliminary affinity results show that representative agonists and antagonists from these series can be used to efficiently covalently label the CCK-A receptor. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase
  作者：Barbara Biasotti、Sabrina Dallavalle、Lucio Merlini、Carlo Farina、Stefania Gagliardi、Carlo Parini、Pietro Belfiore

  DOI：10.1016/s0968-0896(03)00106-8

  日期：2003.5

  Amides of (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy)phenyl)] piperazin-1-yl]propyl]-2,4-pentadienamide (1) and of 5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid (2) are strong inhibitors of the vacuolar ATPase located on the plasma membrane of osteoclasts. In order to understand which V-ATPase subunit is involved in the interaction with these novel inhibitors, analogues containing a photoactivable group and an iodine atom were designed. A series of alcohols or amines containing the photoactivable trifluoroaziridinophenyl or benzophenone moiety and an iodine atom were linked to the above acids via an ester or amide group. These compounds could be thereafter used as a radioactive photoprobe to label the protein. Whereas the compounds containing the photoactivable groups maintained good inhibitory activity, the introduction of the bulky iodine atom was generally detrimental, decreasing potency significantly. Better results were obtained by linking. 3-(4-amino-piperidinomethyl)-3'-iodobenzophenone to 3-ethoxy-4-(2-(5,6-dichlorobenzimidazolyl))benzoic acid to give the corresponding amide 27, that inhibited vacuolar ATP-ase with a IC50 = 140 nM. The feasibility of introducing a radioactive 1211 atom,was ascertained by exchanging the iodine with a tributylstannyl group, that was again substituted by iodine. (C) 2003 Elsevier Science Ltd. All rights reserved.