ω-bromo-p-chloroacetophenone oxime | 136978-96-6

• 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: ω-bromo-p-chloroacetophenone oxime
• 英文别名: 2-bromo-1-(4-chlorophenyl)-ethanone oxime；2-Brom-1-(4-chlor-phenyl)-aethanon-oxim；N-[2-Bromo-1-(4-chlorophenyl)ethylidene]hydroxylamine；N-[2-bromo-1-(4-chlorophenyl)ethylidene]hydroxylamine
• CAS: 136978-96-6
• 化学式: C₈H₇BrClNO
• 分子量: 248.507
• InChiKey: UXUYADQBOMGCBR-UHFFFAOYSA-N

物化性质

• 沸点：
  324.6±27.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 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：
  2

反应信息

• 作为反应物：
  描述：

  ω-bromo-p-chloroacetophenone oxime 在 三乙烯二胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 3.5h， 生成 N-acetoxy-4-(p-chlorophenyl)thiazole-2(3H)-thione
  参考文献：
  名称：

  Towards Improved Alkoxyl Radical Precursors - The Synthesis of N-Alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones

  摘要：

  4-(对氯苯基)-3-羟基噻唑-2(3H)-硫酮(3)可从对氯乙酰苯(1)制备，产率高且产量足够。通过相应的钾盐或四乙基铵盐对环状硫代羟肟酸3进行O-烷基化，得到酯4。稍作修改的程序可将酸3转化为混合酸酐5。酯4和酸酐5是无色至淡黄色的晶体化合物，具有良好的储存稳定性。可见光光解N-烷氧基衍生物4e-g与活性氢供体，通过烷氧自由基途径生成取代的四氢呋喃7或四氢吡喃8。

  DOI：

  10.1055/s-1997-5754
• 作为产物：
  描述：

  对氯苯乙酮 在 溴 、 羟胺 作用下， 生成 ω-bromo-p-chloroacetophenone oxime
  参考文献：
  名称：

  Insulinomimetic Vanadyl–Hydroxythiazolethione Complexes with VO(S₂O₂) Coordination Mode: The Correlation between the Activity and Hammett’s Substituent Constant

  摘要：

  合成了四种以VO(S2O2)配位模式的钒酰氢氧噻唑硫醇复合物，并首次证明了类胰岛素活性明显与配体的哈密特取代基常数相关。

  DOI：

  10.1246/cl.2004.1274

文献信息

• A New Generation of Alkoxyl Radical Precursors – Preparation and Properties ofN-(Alkoxy)-4-arylthiazole-2(3H)-thiones
  作者：Jens Hartung、Michaela Schwarz、Ingrid Svoboda、Hartmut Fuess、Maria Teresa Duarte

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1275::aid-ejoc1275>3.0.co;2-2

  日期：1999.6

  efficient synthesis from p-substituted acetophenones. Alkylation of heterocycles 6–10 in the form of their potassium or tetraalkylammonium salts 11–15 affords N-alkoxy-4-arylthiazole-2(3H)-thiones 16–20 in good to satisfactory yields. The hitherto unknown thiones 16–20 have been subjected to a detailed structural investigation (NMR spectroscopy and X-ray crystallography) and furthermore to a mechanistic

  N-(Hydroxy)thiazole-2(3H)-thiones 6–10 已通过对取代苯乙酮的短而有效的合成制备。杂环 6-10 以其钾盐或四烷基铵盐 11-15 的形式烷基化得到 N-烷氧基-4-芳基噻唑-2(3H)-硫酮 16-20，产率令人满意。迄今为止未知的硫酮 16-20 已经进行了详细的结构研究（核磁共振光谱和 X 射线晶体学），并进一步进行了机械研究，以探索它们作为溶液中以氧为中心的自由基来源的效用。从这些研究的结果中，可以得出以下结论：(i) 对氯苯基取代的酸 9、O-烷基衍生物 19c、19f 和 O-混合酸酐 19k 的 X 射线分析表明短 C-S 债券 [C2-S2 = 1.637(5)-1。684(2) A] 和长 N-O 连接性 [N3-O1 = 1.369(3)-1.379(2) A] 在硫代异羟肟酸酯官能团中。此外，O1 处的 O-烷基-或 O-酰基取代基被扭出噻唑硫酮平面约
• Synthesis and Beckmann rearrangement of novel (Z)-2-organylselanyl ketoximes: promising agents against grapevine anthracnose infection
  作者：Bianca Waskow、Renata A. Mano、Rafaela X. Giacomini、Daniela H. Oliveira、Ricardo F. Schumacher、Ethel A. Wilhelm、Cristiane Luchese、Lucielli Savegnago、Raquel G. Jacob

  DOI：10.1016/j.tetlet.2016.10.078

  日期：2016.12

  substitution reaction of E/Z mixtures of 2-bromo ketoximes with nucleophilic species of selenium, which were generated in situ by simple cleavage of diorganyl diselenides with NaBH4 using ethanol/THF as solvent. The new 2-organylselanyl ketoximes were synthesized in moderate to good yields and with selectivity for the (Z)-configuration. The synthesized (Z)-2-arylselanylacetophenone oximes were submitted to

  我们在这里介绍2（溴）肟的E / Z混合物与硒的亲核物种的亲核取代反应的新型（Z）-2-有机基硒基酮肟的合成，这是通过使用NaBH 4用二有机基二硒化物简单裂解原位生成的乙醇/ THF为溶剂。合成了新型的2-有机基硒基酮肟，产率中等至良好，对（Z）-构型具有选择性。将合成的（Z）-2-芳基硒基苯乙酮肟进行贝克曼重排，得到相应的N-芳基-2-（硒基）乙酰胺。（Z）-1-苯基-2-（苯基硒基）酮肟在DPPH，ABTS，FRAP和脂质过氧化测定中具有对安非他命的噬菌体的抗真菌活性，并在体外具有良好的抗氧化活性。
• Potential of Vitamin B6 Dioxime Analogues to Act as Cholinesterase Ligands
  作者：Dajana Gašo Sokač、Antonio Zandona、Sunčica Roca、Dražen Vikić-Topić、Gabriela Lihtar、Nikola Maraković、Valentina Bušić、Zrinka Kovarik、Maja Katalinić

  DOI：10.3390/ijms232113388

  日期：——

  Seven pyridoxal dioxime quaternary salts (1–7) were synthesized with the aim of studying their interactions with human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The synthesis was achieved by the quaternization of pyridoxal monooxime with substituted 2-bromoacetophenone oximes (phenacyl bromide oximes). All compounds, prepared in good yields (43–76%) and characterized by 1D and 2D NMR spectroscopy, were evaluated as reversible inhibitors of cholinesterase and/or reactivators of enzymes inhibited by toxic organophosphorus compounds. Their potency was compared with that of their monooxime analogues and medically approved oxime HI-6. The obtained pyridoxal dioximes were relatively weak inhibitors for both enzymes (Ki = 100–400 µM). The second oxime group in the structure did not improve the binding compared to the monooxime analogues. The same was observed for reactivation of VX-, tabun-, and paraoxon-inhibited AChE and BChE, where no significant efficiency burst was noted. In silico analysis and molecular docking studies connected the kinetic data to the structural features of the tested compound, showing that the low binding affinity and reactivation efficacy may be a consequence of a bulk structure hindering important reactive groups. The tested dioximes were non-toxic to human neuroblastoma cells (SH-SY5Y) and human embryonal kidney cells (HEK293).

  合成了七种吡哆醛二肟季铵盐（1-7），旨在研究它们与人类乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的相互作用。合成是通过将吡哆醛单肟与取代的2-溴乙酰苯肟（苯乙酰溴肟）季铵化而实现的。所有化合物均以良好的收率（43-76％）制备，并通过1D和2D NMR光谱表征，被评估为乙酰胆碱酯酶的可逆抑制剂和/或被有毒有机磷化合物抑制的酶的再活化剂。它们的效力与其单肟类似物和经医学批准的肟类HI-6进行了比较。所得的吡哆醛二肟对两种酶都是相对较弱的抑制剂（Ki = 100-400 µM）。结构中的第二个肟基与单肟类似物相比并没有改善结合。在重新激活被VX、塔本和对硫磷酸酯抑制的AChE和BChE方面也是如此，没有观察到显着的效率爆发。通过计算机模拟和分子对接研究，将动力学数据与测试化合物的结构特征联系起来，表明低结合亲和力和再活化效力可能是由于臃肿的结构阻碍了重要的反应基团。测试的二肟对人神经母细胞瘤细胞（SH-SY5Y）和人胚胎肾细胞（HEK293）无毒。
• 10.1016/j.tetlet.2024.155183
  作者：Li, Xia、Li, Wen-Sheng、Fu, Xiao、Wan, Wen-Juan、Wang, Li-Xin

  DOI：10.1016/j.tetlet.2024.155183

  日期：——

  isatin –cyclic azomethine 1,3-dipole and nitrosoalkenes in situ generated from α-haloketone oximes has been disclosed. This new protocol is tolerable for a series of substrates and a novel series of seven-membered spiro oxindoles containing oxygen and nitrogen atoms were obtained in moderate to good yields (up to 83 %) under mild conditions.

  已经公开了靛红-环状偶氮甲碱1,3-偶极子和由α-卤代酮肟原位生成的亚硝基烯烃之间的新的[4 + 3]成环。这种新方案适用于一系列底物，并且在温和条件下以中等至良好的收率（高达 83%）获得了一系列含有氧和氮原子的新型七元螺吲哚。
• N-HYDROXY-4-(p-CHLOROPHENYL)THIAZOLE-2(3H)-THIONE
  作者：Hartung, Jens、Schwarz, Michaela、Tangirala, Raghuram S.、Curran, Dennis P.

  DOI：10.15227/orgsyn.079.0228

  日期：——