2,2,2-trifluoro-N-hydroxyacetimidoyl bromide | 44637-25-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 2,2,2-trifluoro-N-hydroxyacetimidoyl bromide
• 英文别名: trifluoroacetohydroximoyl bromide；2,2,2-Trifluoro-N-hydroxyethanimidoyl bromide；2,2,2-trifluoro-N-hydroxyethanimidoyl bromide
• CAS: 44637-25-4
• 化学式: C₂HBrF₃NO
• 分子量: 191.935
• InChiKey: JFRPJKPEZUJXMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-hydroxyacetimidoyl bromide 、 二苯基甲烷硫酮 在 三乙胺 作用下， 以 乙醚 为溶剂， 以95%的产率得到5,5-Diphenyl-3-(trifluoromethyl)-1,4,2-oxathiazole
  参考文献：
  名称：

  Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones

  摘要：

  Fluorinated acetonitrile oxides, generated from the corresponding hydroximoyl bromides in the presence of aryl, hetaryl, ferrocenyl, and cycloaliphatic thioketones, undergo efficient [3 + 2]-cycloadditions to give 3-fluoroalkylated 1,4,2-oxathiazoles in good to excellent yields. The reactions proceed regioselectively with no competitive formation of furoxans as dimers of the intermediate 1,3-dipoles.

  DOI：

  10.1016/j.jfluchem.2017.04.011
• 作为产物：
  描述：

  1-chloro-1,2,2,2-tetrafluoro-1-nitroso-ethane 在 溴 、 苯酚 作用下， 以 乙醚 为溶剂， 生成 2,2,2-trifluoro-N-hydroxyacetimidoyl bromide
  参考文献：
  名称：

  Dyatkin,B.L. et al., Journal of general chemistry of the USSR, 1966, vol. 36, # 7, p. 1340 - 1343

  摘要：

  DOI：

文献信息

• Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C–H arylation
  作者：Jian-Siang Poh、Cristina García-Ruiz、Andrea Zúñiga、Francesca Meroni、David C. Blakemore、Duncan L. Browne、Steven V. Ley

  DOI：10.1039/c6ob00970k

  日期：——

  conditions for the preparation of a range of trifluoromethylated isoxazole building blocks through the cycloaddition reaction of trifluoromethyl nitrile oxide. It was found that controlling the rate (and therefore concentration) of the formation of the trifluoromethyl nitrile oxide was Critical for the preferential formation of the desired isoxazole products versus the furoxan dimer. Different conditions were

  我们报告了通过三氟甲基腈的环加成反应制备一系列三氟甲基化的异恶唑结构单元的条件。已发现控制三氟甲基丁腈氧化物的形成速率（以及浓度）对于优先形成所需的异恶唑产物比呋喃二聚体。针对芳基和烷基取代的炔烃优化了不同的条件。此外，已针对这些结构单元简要探讨了异恶唑4位的反应性。分子间CH-H芳基化，锂化和亲电淬灭以及烷氧基化的条件均通过简短的底物作用域确定，这表明对一系列功能的有用耐受性。最后，开发了通过分子内环化或分子间交叉偶联进行结构多样化的互补过程。
• [EN] PERFLUORINATED CYCLOPROPYL FUSED 1,3-OXAZIN-2-AMINE COMPOUNDS AS BETA-SECRETASE INHIBITORS AND METHODS OF USE<br/>[FR] COMPOSÉS À BASE DE 1,3-OXAZIN-2-AMINE FUSIONNÉE AVEC DU CYCLOPROPYLE PERFLUORÉ UTILISABLES EN TANT QU'INHIBITEURS DE LA BÊTA-SÉCRÉTASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2014138484A1

  公开（公告）日：2014-09-12

  PERFLUORINATED CYCLOPROPYL FUSED 1,3-OXAZIN-2-AMINE COMPOUNDS AS BETA-SECRETASE INHIBITORS AND METHODS OF USE ABSTRACT OF THE DISCLOSURE The present invention provides a new class of compounds useful for the modulation of beta-secretase enzyme (BACE) activity. The compounds have a general Formula I: INSERT STRUCTURE HERE} I wherein variables A4, A5, A6, A8, each of Ra, Rb, R1, R2, R3 and R7 of Formula I, independently, are defined herein. The invention also provides pharmaceutical compositions comprising the compounds, and uses of the compounds and compositions for treatment of disorders and/or conditions related to A-beta plaque formation and deposition, resulting from the biological activity of BACE. Such BACE mediated disorders include, for example, Alzheimer's Disease, cognitive deficits, cognitive impairments, schizophrenia and other central nervous system conditions. The invention further provides compounds of Formulas II and III, and sub-formula embodiments thereof, intermediates and methods for preparing compounds of the invention.

  本发明提供了一类新的化合物，用于调节β-分泌酶（BACE）活性。这些化合物具有一般的化学式I：在此插入结构} I，其中变量A4、A5、A6、A8，以及化学式I中的每个Ra、Rb、R1、R2、R3和R7，在本文中分别定义。该发明还提供了包含这些化合物的药物组合物，以及用于治疗与A-beta斑块形成和沉积相关的疾病和/或症状的化合物和组合物的用途，这些疾病和症状是由BACE的生物活性引起的。这种由BACE介导的疾病包括阿尔茨海默病、认知缺陷、认知障碍、精神分裂症和其他中枢神经系统疾病。该发明还提供了化学式II和III的化合物，以及其亚式化合物、中间体和制备本发明化合物的方法。
• One-Pot Synthesis of Trifluoromethylated Iodoisoxazoles via the Reaction of Trifluoroacetohydroximoyl Chloride with Terminal Alkynes and N-Iodosuccinimide
  作者：Jianmin Zhang、Yongming Wu、Yuwei Guo、Xiaojun Wang、Zhentong Zhu

  DOI：10.1055/s-0035-1562115

  日期：——

  Trifluoromethylated iodoisoxazoles have been synthesized by the reaction of trifluoroacetohydroximoyl chloride, alkynes, and N-iodosuccinimide in a one-pot reaction under metal-free and mild conditions. An array of iodoisoxazole compounds with a wide range of functionalities was obtained in moderate to good yields. The iodine-substituted isoxazoles render versatile reaction sites for subsequent conversion

  三氟甲基化碘异恶唑是通过三氟乙酰羟肟酰氯、炔烃和 N-碘代琥珀酰亚胺在无金属和温和条件下的一锅反应合成的。以中等至良好的产率获得了一系列具有广泛官能团的碘异恶唑化合物。碘取代的异恶唑为后续转化提供了通用的反应位点。基于对照实验提出了合理的途径。
• Cydoadditions of Trifluoroacetonitrile Oxide with Olefins and Acetylenes
  作者：Kiyoshi Tanaka、Hideyuki Masuda、Keiryo Mitsuhashi

  DOI：10.1246/bcsj.57.2184

  日期：1984.8

  The regio- and stereoselectivity of the cydoadditions of trifluoroacetonitrile oxide (1) with olefins and acetylenes were described. The oxide 1, generated in situ from trifluoroacetohydroximoyl bromide etherate in the presence of triethylamine, reacted with various monosubstituted olefins and acetylenes to give exclusively 5-substituted 3-trifluoromethyl-2-isoxazolines and -isoxazoles, respectively

  描述了三氟乙腈氧化物 (1) 与烯烃和乙炔的环加成反应的区域选择性和立体选择性。在三乙胺的存在下，由三氟乙酰羟肟基溴醚化物原位生成的氧化物 1 与各种单取代烯烃和乙炔反应，分别生成 5-取代的 3-三氟甲基-2-异恶唑啉和 -异恶唑，而 1 与 1,2 -二取代的烯烃和乙炔导致形成两种区域异构产物的混合物。另一方面，1 与 (Z)-β-甲基苯乙烯的环加成得到由两种保留 Z-构型的区域异构异恶唑啉和一种非对映异构异恶唑啉组成的混合物。
• [EN] AMINO PYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL 3-KINASE INHIBITORS<br/>[FR] DÉRIVÉS AMINÉS DE PYRIDINE UTILISABLES EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL 3-KINASE
  申请人：NOVARTIS AG

  公开号：WO2015162456A1

  公开（公告）日：2015-10-29

  The present invention provides compounds of formula (I) which inhibit the activity of PI 3-kinase gamma isoform, which are useful for the treatment of diseases mediated by the activation of PI 3-kinase gamma isoform.

  本发明提供了公式(I)的化合物，这些化合物抑制PI 3-激酶γ异构体的活性，对于治疗由PI 3-激酶γ异构体激活介导的疾病是有用的。