3-(三氟甲基)-1H-吲唑 | 57631-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 3-(三氟甲基)-1H-吲唑
• 英文名称: 3-trifluoromethyl-1H-indazole
• 英文别名: 3-trifluoromethylindazole；3-(trifluoromethyl)-1H-indazole；3-(trifluoromethyl)-2H-indazole
• CAS: 57631-05-7
• 化学式: C₈H₅F₃N₂
• mdl: MFCD11111669
• 分子量: 186.136
• InChiKey: PJVACBOIQLBALV-UHFFFAOYSA-N

物化性质

• 沸点：
  268.5±35.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(三氟甲基)-1H-吲唑 在 tris(dibenzylideneacetone)dipalladium (0) 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 53.0h， 生成
  参考文献：
  名称：

  Design and synthesis of pyridine–pyrazolopyridine-based inhibitors of protein kinase B/Akt

  摘要：

  Thr-211 is one of three different amino acid residues in the kinase domain of protein kinase B/Akt as compared to protein kinase A (PKA), a closely related analog in the same AGC family. In an attempt to improve the potency and selectivity of our indazole-pyridine series of Akt inhibitors over PKA, efforts have focused on the incorporation of a chemical functionality to interact with the hydroxy group of Thr-211. Several substituents including an oxygen anion, amino, and nitro groups have been introduced at the C-6 position of the indazole scaffold, leading to a significant drop in Akt potency. Incorporation of a nitrogen atom into the phenyl ring at the same position (i.e., 9f) maintained the Akt activity and, in some cases, improved the selectivity over PKA. The structure-activity relationships of the new pyridine-pyrazolopyridine series of Akt inhibitors and their structural features when bound to PKA are also discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.010
• 作为产物：
  描述：

  2,2,2-trifluoro-1-(2-nitrophenyl)ethanone 在 一氧化碳 、 pentamethylcyclopentadienyl dicarbonyl iron(II) dimer 、 盐酸羟胺 作用下， 以 1,4-二氧六环 、 吡啶 、 乙醇 为溶剂， 150.0 ℃ 、5.07 MPa 条件下， 反应 163.0h， 生成 3-(三氟甲基)-1H-吲唑
  参考文献：
  名称：

  Synthesis of 1H-Indazoles by Reductive Cyclization of o-Nitro-ketoximes

  摘要：

  DOI：

  10.3987/com-03-9926

文献信息

• [EN] SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE<br/>[FR] INHIBITEURS SÉLECTIFS DE MUTANTS CLINIQUEMENT IMPORTANTS DE LA TYROSINE KINASE DE L'EGFR
  申请人：CS PHARMASCIENCES INC

  公开号：WO2017120429A1

  公开（公告）日：2017-07-13

  The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof, or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof, and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.

  本发明提供了式（I）的化合物或其亚类结构或种属，或其药学上可接受的盐、酯、溶剂化合物和/或前药，以及用于治疗或改善异常细胞增殖性疾病，如癌症的方法和组合物，其中A、R2、R3、R10、E1、E2、E3、Y和Z如本文所定义。
• [EN] COMPOUNDS FOR THE TREATMENT OF HIV<br/>[FR] COMPOSÉS POUR TRAITER LE VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2013006738A1

  公开（公告）日：2013-01-10

  The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula I and therapeutic methods for treating a Retroviridae viral infection including an infection caused by the HIV virus.

  本发明提供了如下式（I）的化合物或其盐，还提供了包含如下式（I）化合物的药物组合物，制备如下式（I）化合物的方法，用于制备如下式（I）化合物的中间体以及治疗Retroviridae病毒感染的治疗方法，包括由HIV病毒引起的感染。
• The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles
  作者：Johannes Teichert、Pascal Oulié、Kane Jacob、Laure Vendier、Michel Etienne、Rosa M. Claramunt、Concepción López、Carlos Pérez Medina、Ibon Alkorta、José Elguero

  DOI：10.1039/b617988f

  日期：——

  The structures of three NH-indazoles (3-methyl, 3-trifluoromethyl and 3-trifluoromethyl-4,5,6,7-tetrafluoroindazoles) have been determined by X-ray crystallography. These three compounds, together with 3-methyl-4,5,6,7-tetrafluoroindazole, whose X-ray structure could not be determined, have been studied using multinuclear magnetic resonance spectroscopy, including solid-state CPMAS. They all are 1H-tautomers. In the crystal, 3-methyl-1H-indazole forms hydrogen bonded dimers, whereas 3-trifluoromethyl-1H-indazole and 3-trifluoromethyl-4,5,6,7-tetrafluoro-1H-indazole crystallize as catemers. These catemers are chiral space group P32. They are the first examples of indazoles crystallizing in the form of helices of three-fold screw axis. Attempts at rationalizing this behavior on the basis of supramolecular interactions (hydrogen bonds and aromatic interactions) and GIAO calculations are discussed.

  通过 X 射线晶体学，确定了三种 NH-吲唑（3-甲基、3-三氟甲基和 3-三氟甲基-4,5,6,7-四氟吲唑）的结构。这三种化合物，连同无法确定其 X 射线结构的 3-甲基-4,5,6,7-四氟吲唑，已通过多核磁共振光谱法（包括固态 CPMAS）进行了研究。它们都是 1H 同分异构体。在晶体中，3-甲基-1H-吲唑形成氢键二聚体，而 3-三氟甲基-1H-吲唑和 3-三氟甲基-4,5,6,7-四氟-1H-吲唑则结晶为同系物。这些对映体属于手性空间群 P32。它们是吲唑以三折螺旋轴螺旋形式结晶的首个实例。本文讨论了在超分子相互作用（氢键和芳香族相互作用）和 GIAO 计算的基础上合理解释这种行为的尝试。
• A straightforward access to 3-trifluoromethyl-1H-indazoles via (3+2)-cycloaddition of arynes with nitrile imines derived from trifluoroacetonitrile
  作者：Anna Kowalczyk、Greta Utecht-Jarzyńska、Grzegorz Mlostoń、Marcin Jasiński

  DOI：10.1016/j.jfluchem.2020.109691

  日期：2021.1

  In situ generated arynes react with nitrile imines derived from trifluoroacetonitrile at 0 °C in THF solutions yielding 3-trifluoromethyl-1H-indazole derivatives as the only intermolecular products. The reaction corresponds the expected (3 + 2)-cycloadditions which belong to the Type III (inverse-electron-demand) of Sustmann’s classification. Subsequent CAN-mediated dearylation of the model N-(p-methoxy)phenyl

  原位生成的芳烃与三氟乙腈的腈亚胺在0°C的THF溶液中反应，生成3-三氟甲基-1 H-吲唑衍生物作为唯一的分子间产物。该反应对应于预期的（3 + 2）-环加成，该加成属于Sustmann分类的III型（电子逆需求）。随后的CAN介导的模型N-（对甲氧基）苯基吲唑的脱芳基反应导致N-未取代的类似物，其易于进行烷基化和酰化反应。提出的方案为制备3-CF 3取代的吲唑衍生物提供了一种优越的方法。
• Fluorinated indazole derivatives and a process for their preparation
  申请人：Produits Chimiques Ugine Kuhlmann

  公开号：US04051145A1

  公开（公告）日：1977-09-27

  Compound of the formula: ##STR1## in which the nucleus A is unsubstituted or substituted by one or two nitro, amino, alkyl, alkoxy, chlorine or bromine and the alkyl and alkoxy each contain up to two carbon atoms and process for the preparation of such compounds which comprises diazotizing an aniline of the formula: ##STR2## in which the nucleus A is unsubstituted or substituted by one or two nitro, amino, alkyl, alkoxy, chlorine or bromine, the alkyl and alkoxy each containing up to two carbon atoms and cyclizing the diazo derivative obtained.

  化合物的公式为：##STR1## 其中，核A未被取代或被一或两个硝基，氨基，烷基，烷氧基，氯或溴取代，而烷基和烷氧基每个都含有最多两个碳原子，并且制备这种化合物的方法包括对公式为：##STR2## 的苯胺进行重氮化，其中核A未被取代或被一或两个硝基，氨基，烷基，烷氧基，氯或溴取代，而烷基和烷氧基每个都含有最多两个碳原子，然后使得重氮衍生物环化。