trifluoracetamidoaniline | 22902-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trifluoracetamidoaniline
• 英文别名: o-Amino-trifluoracetanilid；n-(2-Aminophenyl)-2,2,2-trifluoroacetamide
• CAS: 22902-31-4
• 化学式: C₈H₇F₃N₂O
• 分子量: 204.152
• InChiKey: YWBWHUHKSASUBK-UHFFFAOYSA-N

物化性质

• 沸点：
  297.2±40.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  55.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trifluoracetamidoaniline 在 Montmorillonite K₁₀ 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 以87%的产率得到2-(三氟甲基)苯并咪唑
  参考文献：
  名称：

  新型蒙脱石2-三氟甲基芳基咪唑新合成K10 en'milieu sec'sous micro-onde

  摘要：

  的环化缩合ñ - （carbotrifluoromethyl） -邻-arylenediamines导致对蒙脱土K10在“干媒体”在2分钟内在家用烤箱一系列2-trifluoromethylarylimidazoles具有良好产率微波辐射下。在相同条件下通过常规加热，未观察到反应。

  DOI：

  10.1016/s0040-4020(00)00992-3
• 作为产物：
  描述：

  2,2,2-三氟乙酰胺 、 2-溴苯胺 在 copper(l) iodide potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 以6%的产率得到trifluoracetamidoaniline
  参考文献：
  名称：

  铜催化的芳基卤化物和2,2,2-三氟乙酰胺的合成芳基伯胺

  摘要：

  开发了一种催化方法，可以在温和的条件下从相应的芳基溴化物和碘化物合成伯芳基胺（收率= 80–99％）。结晶2,2,2-三氟乙酰胺被用作氨替代物，而CuI / N，N'-二甲基乙二胺被用作催化剂以实现C-N交叉偶联。

  DOI：

  10.1016/j.tetlet.2007.11.012

文献信息

• Solid phase synthesis of arylretinamides
  申请人：——

  公开号：US20030105164A1

  公开（公告）日：2003-06-05

  A solid phase synthetic method for preparing arylretinamides is provided. The method comprises reacting hexachloroacetone with a solvent-suspended resin-bound triphenylphosphine to provide a suspension comprising an activated chlorinating reagent; reacting retinoic acid with the activated chlorinating reagent to provide retinoyl chloride; adding pyridine and a select arylamine to the resulting mixture; and stirring the resulting mixture for a time and at a temperature sufficient for the select arylamine to react with the retinoyl chloride and provide the arylretinamide. Also provided, are select arylretinamides that can be prepared by the present method, and methods of using such arylretinamides to induce apoptosis in cancer cells.

  提供了一种用于制备芳基维甲酰胺的固相合成方法。该方法包括将六氯乙酮与悬浮于溶剂中的树脂结合的三苯基膦反应，以提供含有活化氯化试剂的悬浮液；将维甲酸与活化氯化试剂反应以提供维甲酰氯；向得到的混合物中加入吡啶和选择的芳基胺；并在足够时间和温度下搅拌得到的混合物，以使选择的芳基胺与维甲酰氯反应并提供芳基维甲酰胺。还提供了可以通过该方法制备的选择性芳基维甲酰胺，以及使用这些芳基维甲酰胺在癌细胞中诱导凋亡的方法。
• 3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy -pyridine, pyrimidine and benzene derivatives as alpha1-adrenoceptor antagonists
  申请人：F. Hoffmann-La Roche AG

  公开号：EP0711757A1

  公开（公告）日：1996-05-15

  The present invention relates to novel α₁-adrenoceptor antagonists of Formula I: in which: p is 0 or 1; t is 0, 1 or 2; X is O, S or NR⁶ (in which R⁶ is hydro or (C₁₋₆)alkyl); Y and Z are independently CH or N; R¹ is hydro, hydroxy, halo, nitro, amino, cyano, (C₁₋₄)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, (C₃₋₆)cycloalkyl(C₁₋₄)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl(C₁₋₄)alkyl, heteroaryl(C₁₋₄)alkyl, (C₁₋₆)alkyloxy, (C₃₋₆)cycloalkyloxy, (C₃₋₆)cycloalkyl(C₁₋₄)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl(C₁₋₄)alkyloxy or heteroaryl(C₁₋₄)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano); R² is hydro, hydroxy, halo, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms); R³ is -C(O)R⁷ (wherein R⁷ is (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, di(C₁₋₄)alkylamino, N-(C₁₋₄)alkyl-N-(C₁₋₄)alkyloxyamino, (C₁₋₄)alkyl((C₁₋₄)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl); R⁴ is halo, hydroxy, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy; and R⁵ is (C₁₋₆)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.

  本发明涉及式 I 的新型 α₁-肾上腺素受体拮抗剂： 其中 p 是 0 或 1； t 是 0、1 或 2 X 是 O、S 或 NR⁶（其中 R⁶ 是氢或 (C₁₋₆)烷基）； Y 和 Z 独立地为 CH 或 N； R¹是氢、羟基、卤代、硝基、氨基、氰基、(C₁₋₄)烷硫基、乙酰氨基、三氟乙酰氨基、甲磺酰氨基、(C₁₋₆)烷基、(C₃₋₆)环烷基、(C₃₋₆)环烷基(C₁₋₄)烷基、噁唑-2-基、芳基、杂芳基、芳基(C₁₋₄)烷基、杂芳基(C₁₋₄)烷基、(C₁₋₆)烷氧基、(C₃₋₆)环烷氧基、(C₃₋₆)环烷基(C₁₋₄)烷氧基，2-丙炔氧基，芳基氧基，杂芳基氧基、芳基（C₁₋₄）烷氧基或杂芳基（C₁₋₄）烷氧基（其中烷基任选被一至三个卤原子取代，芳基或杂芳基任选被一至两个独立选自卤素和氰基的取代基取代）； R² 是氢、羟基、卤代、氰基、(C₁₋₆)烷基或(C₁₋₆)烷氧基（其中烷基任选被一至三个卤原子取代）； R³ 是 -C(O)R⁷（其中 R⁷ 是 (C₁₋₆)烷基、(C₃₋₆)环烷基、二(C₁₋₄)烷基氨基、N-(C₁₋₄)烷基-N-(C₁₋₄)烷氧基氨基、(C₁₋₄)烷基((C₁₋₄烷氧基)氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基)； R⁴ 是卤素、羟基、氰基、(C₁₋₆)烷基或 (C₁₋₆)烷氧基；和 R⁵ 是 (C₁₋₆)烷基；及其药学上可接受的盐和 N-氧化物。
• Pyrimidinedione, pyrimidinetrione, triazinedione, tetrahydroquinazolinedione derivatives as alpha-1-adrenergic receptor antagonists
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0748800A2

  公开（公告）日：1996-12-18

  The present invention relates to novel α1-adrenoceptor antagonists of the formula I in which: R1 is acetylamino, amino, cyano, trifluoroacetylamino, halo, hydro, hydroxy, nitro, methylsulfonylamino, 2-propynyloxy, a group selected from (C1-6)alkyl, (C3-6)cycloalkyl, (C3-6)cycloalkyl(C1-4)alkyl, (C1-6)alkyloxy, (C3-6)cycloalkyloxy, (C3-6)cycloalkyl(C1-4)alkyloxy and (C1-4)alkylthio (which group is optionally further substituted with one to three halo atoms) or a group selected from aryl, aryl(C1-4)alkyl, heteroaryl, heteroaryl(C1-4)alkyl, aryloxy, aryl(C1-4)alkyloxy, heteroaryloxy and heteroaryl(C1-4)alkyloxy (which aryl and heteroaryl are optionally further substituted with one to two radicals independently selected from halo and cyano); R2 is cyano, halo, hydro, hydroxy or a group selected from (C1-6)alkyl and (C1-6)alkyloxy (which group is optionally further substituted with one to three halogen atoms); R3 and R4 are both hydro or methyl or together are ethylene; and R5 is a group selected from Formulae (a), (b), (c) and (d): in which: X is C(O), CH2 or CH(OH); Y is CH2 or CH(OH); Z is N or C(R9), wherein R9 is hydro, (C1-6)alkyl or hydroxy; R6 is hydro, a group selected from (C1-6)alkyl, (C3-6)cycloalkyl, (C3-6)cycloalkyl(C1-4)alkyl (which group is optionally further substituted with one to three halo atoms) or a group selected from aryl, heteroaryl, aryl(C1-4)alkyl and heteroaryl(C1-4)alkyl (which aryl and heteroaryl are optionally further substituted with one to three radicals selected from halo, cyano, (C1-6)alkyloxy, (C1-6)alkyl and aryl); R7 is (C1-6)alkanoyl, carbamoyl, cyano, di(C1-6)alkylamino, halo, hydro, hydroxy, hydroxyiminomethyl, (C1-6)alkylsulfonyl, (C1-6)alkylthio, a group selected from (C1-6)alkyl, (C3-6)cycloalkyl, (C1-6)alkyloxy and (C1-6)alkyloxy(C1-4)alkyl (which group is optionally further substituted with one to three radicals selected from halo, hydroxy or (C1-6)alkyloxy) or a group selected from aryl, heteroaryl, aryl(C1-4)alkyl and heteroaryl(C1-4)alkyl (which aryl and heteroaryl are optionally further substituted with one to three radicals selected from halo, cyano, (C1-6)alkyloxy, (C1-6)alkyl and aryl) or R7 and R9 together are tetramethylene; and each R8 is independently hydro, hydroxy, methyl or ethyl; and the pharmaceutically acceptable salts and N-oxides thereof.

  本发明涉及式 I 的新型 α1 肾上腺素受体拮抗剂 其中 R1为乙酰氨基、氨基、氰基、三氟乙酰氨基、卤代、氢、羟基、硝基、甲磺酰氨基、2-丙炔氧基、选自(C1-6)烷基、(C3-6)环烷基、(C3-6)环烷基(C1-4)烷基、(C1-6)烷氧基、(C3-6)环烷氧基的基团、(C1-6)烷氧基、(C3-6)环烷氧基、(C3-6)环烷基(C1-4)烷氧基和(C1-4)烷硫基（该基团可选择进一步被一至三个卤原子取代）或选自芳基的基团、芳基、芳基（C1-4）烷基、杂芳基、杂芳基（C1-4）烷基、芳氧基、芳基（C1-4）烷氧基、杂芳氧基和杂芳基（C1-4）烷氧基（其中芳基和杂芳基可任选地被一至两个独立选自卤原子和氰基的基团进一步取代）； R2 是氰基、卤代、氢基、羟基或选自 (C1-6) 烷基和 (C1-6) 烷氧基的基团（该基团可任选进一步被一至三个卤素原子取代）； R3 和 R4 都是羟基或甲基，或一起是乙烯；以及 R5 是选自式(a)、(b)、(c)和(d)的基团： 其中 X 是 C(O)、CH2 或 CH(OH)； Y 是 CH2 或 CH(OH)； Z 是 N 或 C(R9)，其中 R9 是氢、(C1-6)烷基或羟基； R6 是氢、选自(C1-6)烷基、(C3-6)环烷基、(C3-6)环烷基(C1-4)烷基（该基团可任选进一步被一至三个卤原子取代）或选自芳基、杂芳基、芳基(C1-4)烷基和杂芳基(C1-4)烷基（该芳基和杂芳基可任选进一步被一至三个选自卤素、氰基、(C1-6)烷氧基、(C1-6)烷基和芳基的基团取代）的基团； R7 是(C1-6)烷酰基、氨基甲酰基、氰基、二(C1-6)烷基氨基、卤素、氢、羟基、羟基亚氨基甲基、(C1-6)烷基磺酰基、(C1-6)烷硫基、选自(C1-6)烷基、(C3-6)环烷基、(C1-6)烷氧基和(C1-6)烷氧基(C1-4)烷基的基团（该基团可选择进一步被选自卤素、羟基或(C1-6)烷氧基的一至三个基团取代）、羟基或(C1-6)烷氧基)或选自芳基、杂芳基、芳基(C1-4)烷基和杂芳基(C1-4)烷基的基团(其中芳基和杂芳基可选择进一步被一至三个选自卤代、氰基、(C1-6)烷氧基、(C1-6)烷基和芳基的基团取代)或 R7 和 R9 一起为四亚甲基；每个 R8 独立地是氢、羟基、甲基或乙基；以及它们的药学上可接受的盐和 N-氧化物。
• Pyrimidinedione, pyrimidinetrione, triazinedione derivatives as alpha-1-adrenergic receptor antagonists
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0748800B1

  公开（公告）日：2001-05-09
• N-Trifluoroacétylation sélective d'ortho-arylènediamines sous ultrasons
  作者：Khalid Bougrin、André Loupy、Alain Petit、Rachid Benhida、Jean-Louis Fourrey、Boujemâa Daou、Mohamed Soufiaoui

  DOI：10.1016/s0040-4039(00)00723-1

  日期：2000.6

  Mono and di-N-trifluoroacetylation of ortho-arylenediamines can be performed selectively under ultrasound irradiation according to the relative amounts of starting materials. Mono and di-trifluoroacetylated compounds 3 and 4 are prepared with good yields in dry THF during 1 to 2 min sonication. (C) 2000 Elsevier Science Ltd. All rights reserved.