2,2,2-trifluoro-1-phenyl-ethanone oxime-O-(4-hydroxyphenylsulfonate) | 67655-83-8

• 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: 2,2,2-trifluoro-1-phenyl-ethanone oxime-O-(4-hydroxyphenylsulfonate)
• 英文别名: (E)-2,2,2-trifluoro-1-phenylethanon oxime；2,2,2-trifluoro-1-phenylethan-1-one oxime；(E)-2,2,2-trifluoro-1-phenylethanonoxime；1-(hydroxyimino)-1-phenyl-2,2,2-trifluoroethane；1-(hydroximino)-1-phenyl-2,2,2-trifluoroethane；(E)-Trifluoracetophenonoxim；Ethanone, 2,2,2-trifluoro-1-phenyl-, oxime；(NE)-N-(2,2,2-trifluoro-1-phenylethylidene)hydroxylamine
• CAS: 67655-83-8
• 化学式: C₈H₆F₃NO
• 分子量: 189.137
• InChiKey: TUKWYJVGKNCDJJ-KPKJPENVSA-N

物化性质

• 沸点：
  194.1±40.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 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：
  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-1-phenyl-ethanone oxime-O-(4-hydroxyphenylsulfonate) 在 palladium 10% on activated carbon 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以86%的产率得到1-苯基-2,2,2-三氟乙胺
  参考文献：
  名称：

  [EN] THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS
  [FR] THIADIAZOLEDIOXYDES ET THIADIAZOLEOXIDES CONVENANT COMME LIGANDS DES RECEPTEURS DES CXC- ET CC-CHIMIOKINES

  摘要：

  披露了公式（IA）的新颖化合物以及其中医药可接受的盐和溶剂化物。包含取代基A的基团示例包括杂芳基、芳基、杂环烷基、环烷基、芳基、炔基、烯基、氨基烷基、烷基或氨基。包含取代基B的基团示例包括芳基和杂芳基。还披露了一种治疗趋化因子介导的疾病的方法，例如，癌症、血管生成、血管生成性眼病、肺病、多发性硬化症、类风湿性关节炎、骨关节炎、中风和心脏再灌注损伤、急性疼痛、急性和慢性炎症性疼痛，以及使用公式（IA）的化合物的神经性疼痛。

  公开号：

  WO2004033440A1
• 作为产物：
  描述：

  2,2,2-trifluoroacetophenone oxime 以 neat (no solvent, solid phase) 为溶剂， 反应 26298.0h， 生成 2,2,2-trifluoro-1-phenyl-ethanone oxime-O-(4-hydroxyphenylsulfonate)
  参考文献：
  名称：

  Quantum chemical calculation of 19F NMR chemical shifts of trifluoromethyl diazirine photoproducts and precursors

  摘要：

  Irradiation of aryl(trifluoromethyl)diazirines may result in a multitude of products, which are difficult to assign in the F-19 NMR spectrum. In this article, it is demonstrated that an average accuracy of 2.9 ppm (standard deviation) can be achieved by quantum chemical calculations at the B3LYP 6-311G++(2d,2p) level of theory, followed by a Boltzmann weighting of the optimized conformers. A set of 30 compounds was investigated both-experimentally and theoretically. F-19 NMR chemical shifts of precursor Z-oximes and Z-tosyloximes ranged from delta(F) -62.9 to -61.8 ppm, whereas their E counterparts showed shifts between delta(F) -67.2 and -66.2 ppm. Stereochemical assignments were confirmed by two X-ray analyses. Quantum chemical calculation also allowed the assignment of the configuration of an (E,E) azine. Trifluoromethyl diazirines exhibited a delta(F) between -66.1 and -65.6, diaziridines between -76.2 and -75.9 ppm. The smallest delta(F) values were observed for alpha-oxygenated trifluoromethyl compounds (delta(F) -78.9 to -77.4 ppm). The average deviation of the calculated from the experimental values corresponds to only about 1% of the standard F-19 NMR chemical shift range. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.06.027

文献信息

• Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R
  作者：Sabrina Biselli、Merlin Bresinsky、Katharina Tropmann、Lisa Forster、Claudia Honisch、Armin Buschauer、Günther Bernhardt、Steffen Pockes

  DOI：10.1016/j.ejmech.2021.113190

  日期：2021.3

  selectivity profile towards the hH2R, e.g. 157 being at least 3800-fold selective within the histamine receptor family. The structural similarities of our monomeric ligands to pramipexole (6), a dopamine receptor agonist, suggested an investigation of the binding behavior at those receptors. The target compounds were (partial) agonists with moderate affinity at the hD2longR and agonists with high affinity

  即使在今天，组胺H 2受体（H 2 R）在中枢神经系统（CNS）中的作用仍然广为人知。在先前的研究中，许多二聚体，高亲和力和亚型选择性的氨基甲酰基胍型配体，例如UR-NK22（5，p K i  = 8.07）被报道为H 2 R激动剂。但是，它们在中枢神经系统中研究H 2 R的适用性因其分子和药代动力学特性（例如高分子量）而受到限制，因此其生物利用度有限。满足对更多类似毒品的H 2的需求R激动剂具有高亲和力，我们合成了一系列含有各种间隔基和侧链部分的单体（硫代）氨基甲酰基胍型配体。这种结构上的简化导致了有效的（部分）激动剂（豚鼠右心房，[ 35 S]GTPγS和β-arrestin2募集试验），其人类（h）H 2 R亲和力在一位纳摩尔范围内（p K i（139，UR-KAT523）：8.35； p K i（157，UR-MB-69）：8.69）。本文介绍的大多数化合物对hH 2 R表现出出色
• [EN] PYRROLO [3, 2 -E] [1,2,4] TRIAZOLO [1,5 -A] PYRIMIDINES DERIVATIVES AS INHIBITORS OF MICROGLIA ACTIVATION<br/>[FR] DÉRIVÉS DE PYRROLO[3,2-E][1,2,4]TRIAZOLO[1,5-A]PYRIMIDINES EN TANT QU'INHIBITEURS DE L'ACTIVATION MICROGLIALE
  申请人：SENEXIS LTD

  公开号：WO2011042496A1

  公开（公告）日：2011-04-14

  The invention relates to novel compounds useful in the treatment and prophylaxis of disease. Compounds of the formula (I) wherein X is halogen, independently selected form chlorine and fluorine and n is 0, 1 or 2. and their pharmaceutically acceptable salts are useful in the treatment and prophylaxis of diseases caused by activation of microglia, particularly Alzheimer's disease.

  这项发明涉及一种新型化合物，可用于治疗和预防疾病。 公式（I）中的化合物，其中X是卤素，独立选择自氯和氟，n为0、1或2。以及它们的药用盐在治疗和预防由小胶质细胞的活化引起的疾病方面很有用，特别是阿尔茨海默病。
• Oxime ethers, compositions containing them and the use thereof
  申请人：Ciba-Geigy Corporation

  公开号：US04530716A1

  公开（公告）日：1985-07-23

  The oxime ethers of the formula I below are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice, and herbicides are principally chloroacetanilides and thiocarbamates. The oxime ethers have the formula I ##STR1## wherein n is 1 or 2, each of R.sub.1 and R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl each of R.sub.3 and R.sub.4 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl or nitro; each of R.sub.5 and R.sub.6 independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, or together form a 2- to 6-membered alkylene or alkenylene bridge which may be substituted by 1 to 4 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.8 alkoxyalkyl or C.sub.3 -C.sub.8 alkenyloxyalkyl groups; each of A and B independently of the other is oxygen or sulfur, or one of A and B is the methine group, X is a fluorinated C.sub.1 -C.sub.3 alkyl radical which may also additionally contain chlorine, and Y is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy or phenyl.

  化学式I所示的肟醚能够作为解毒剂或安全剂，保护栽培植物免受除草剂的植物毒性影响。这种栽培植物主要是高粱、谷物、玉米和稻米，而除草剂主要是氯乙酰苯胺和硫代氨基甲酸酯。肟醚的化学式如下：其中n为1或2，R.sub.1和R.sub.2分别为氢或C.sub.1 -C.sub.4烷基，R.sub.3和R.sub.4分别为氢、卤素、C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4卤代烷基、C.sub.1 -C.sub.4烷氧基、C.sub.1 -C.sub.4卤代烷氧基、C.sub.1 -C.sub.4烷硫基、C.sub.1 -C.sub.4卤代烷硫基、C.sub.1 -C.sub.4烷基亚砜、C.sub.1 -C.sub.4烷基砜、C.sub.1 -C.sub.4卤代烷基亚砜、C.sub.1 -C.sub.4卤代烷基砜或硝基；R.sub.5和R.sub.6中的每一个独立地为C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4卤代烷基、C.sub.2 -C.sub.8烷氧基烷基、C.sub.3 -C.sub.4烯基、C.sub.3 -C.sub.4炔基，或者一起形成一个2-到6-成员的烷基或烯基桥，该桥可能被1至4个C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4卤代烷基、C.sub.1 -C.sub.4烷氧基、C.sub.2 -C.sub.4烯氧基、C.sub.2 -C.sub.8烷氧基烷基或C.sub.3 -C.sub.8烯氧基烷基基团取代；A和B中的每一个独立地为氧或硫，或者A和B中的一个是亚甲基基团，X是氟化的C.sub.1 -C.sub.3烷基基团，也可能额外含有氯，Y为氢、C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4卤代烷基、C.sub.1 -C.sub.4烷氧基、C.sub.1 -C.sub.4卤代烷氧基或苯基。
• [EN] ISOXAZOLE-5-CARBOXAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS D'ISOXAZOLE-5-CARBOXAMIDE
  申请人：ORGANON NV

  公开号：WO2010089297A1

  公开（公告）日：2010-08-12

  The present invention relates to isoxazole-5-carboxamide derivative having the general Formula (I), or a pharmaceutically acceptable salt thereof, to pharmaceutical compositions comprising the same, as well as to the use of said isoxazole-5-carboxamide derivatives for the treatment of TRPV1 mediated disorders, such as acute and chronic pain disorders, acute and chronic neuropathic pain, acute and chronic inflammatorypain, respiratorydiseases, and lower urinary tract disorders.

  本发明涉及具有一般式（I）的异噁唑-5-羧酰胺衍生物或其药学上可接受的盐，包括含有它们的制药组合物，以及使用该异噁唑-5-羧酰胺衍生物治疗TRPV1介导的疾病，如急性和慢性疼痛疾病、急性和慢性神经病性疼痛、急性和慢性炎症性疼痛、呼吸系统疾病和下尿路疾病的用途。
• Novel oxime ethers, the preparation thereof, compositions containing
  申请人：Ciba-Geigy Corporation

  公开号：US04566901A1

  公开（公告）日：1986-01-28

  The invention relates to novel oxime ethers of the formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R.sub.2 and R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical. These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides. Preferred crops are sorghum, cereals, maize and rice, and herbicides are chiefly chloroacetanilides and thiocarbamates.

  该发明涉及公式I的新型肟醚化合物，其中R.sub.1是氢、卤素、低烷基、低卤代烷基、低烷氧基、低卤代烷氧基、低烷硫基、低卤代烷硫基、低烷基砜基、低烷基磺酰基、低卤代烷基砜基、低卤代烷基磺酰基或硝基，R.sub.2和R.sub.3中的每一个是氢、卤素、低烷基、低烷氧基或低卤代烷氧基，Q是未取代或取代的低烷基、低烯基、低炔基或环烷基、低脂肪酰基基团、可以是取代或未取代的脂肪、环脂肪、芳香或杂环酰基基团、羰基或硫代羰基基团、芳基或芳基烷基基团、酰亚胺基甲基基团、邻苯二甲酰亚胺基甲基基团或杂环基团。这些化合物能够作为抗毒或保护剂，用于保护栽培植物免受侵害性除草剂的毒害作用。首选作物为高粱、谷物、玉米和稻米，主要除草剂为氯乙酰苯胺类和硫代氨基甲酸酯类。