4-(hydroxyimino)hexan-3-one | 53520-52-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(hydroxyimino)hexan-3-one
• 英文别名: 4-Hydroxyiminohexan-3-one
• CAS: 53520-52-8
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: FEXFOJWILSEGPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(hydroxyimino)hexan-3-one 在 溶剂黄146 、 肼 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Discovery and synthesis of tetrahydroindolone derived semicarbazones as selective Kv1.5 blockers

  摘要：

  A novel class of tetrahydroindolone-derived semicarbazones has been discovered as potent Kv 1.5 blockers. in in vitro studies, several compounds exhibited very good potency for blockade of Kv 1.5. Compound 8i showed good selectivity for blockade of Kv1.5 vs hERG and L-type calcium channels. In an anesthetized pig model, compounds 8i and 10c increased atrial ERP about 28%, 18%, respectively, in the right atrium without affecting ventricular ERP. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.057
• 作为产物：
  描述：

  3-己酮 在 盐酸 、 亚硝酸正戊酯 作用下， 以 乙醚 为溶剂， 生成 4-(hydroxyimino)hexan-3-one
  参考文献：
  名称：

  Bernadou; Quan, European Journal of Medicinal Chemistry, 1975, vol. 10, # 6, p. 599 - 601

  摘要：

  DOI：

文献信息

• Dual Photoredox/Palladium-Catalyzed C–H Acylation of 2-Arylpyridines with Oxime Esters
  作者：Xiao-Peng Liu、Jia-Rong Chen、Bin-Qing He、Yuan Gao、Peng-Zi Wang、Hong Wu、Hong-Bin Zhou

  DOI：10.1055/s-0040-1707252

  日期：2021.3

  unprecedented dual photoredox/palladium-catalyzed iminyl-radical-mediated C–C bond cleavage and directed ortho C–H acylation of 2-arylpyridines by using oxime esters is described. Oxime esters can serve as efficient acyl sources through formation of the corresponding acyl radicals by photoredox-catalyzed iminyl-radical-mediated C–C bond cleavage. This redox-neutral protocol features excellent regioselectivity

  描述了一种前所未有的双光氧化还原/钯催化亚胺基-自由基介导的 C-C 键裂解和使用肟酯的 2-芳基吡啶的定向邻位 C-H 酰化。肟酯可以通过光氧化还原催化亚胺基介导的 C-C 键裂解形成相应的酰基自由基作为有效的酰基来源。这种氧化还原中性方案具有出色的区域选择性、广泛的底物范围和对两种组分的良好官能团耐受性，提供广泛的芳基酮，通常具有良好的产率。
• Discovery of a series of ruthenium(II) derivatives with α -dicarbonylmonoxime as novel inhibitors of cancer cells invasion and metastasis
  作者：Yihui He、Huiying Xue、Wendian Zhang、Li Wang、Guangya Xiang、Lei Li、Xianmei Shang

  DOI：10.1016/j.jorganchem.2017.05.024

  日期：2017.8

  A series of novel ruthenium(II)-cymene complexes (1–9) with substituted α-dicarbonylmonoximes of general formula [Ru(η6-cymene)(L)Cl] (L = N,O-chelating bidentate α-dicarbonylmonoxime derivatives) have been synthesized and characterized by elemental analysis, IR, 1H NMR, 13C NMR spectroscopies, and in three cases by single crystal X-ray diffraction analysis. The most effective compound 9 displays remarkable

  一系列新颖的钌（II）配合物-cymene（1 - 9）与取代α通式-dicarbonylmonoximes的[Ru（η 6 -cymene）（L）CL]（L = N，O-二齿螯合α -dicarbonylmonoxime衍生物）已通过元素分析，IR，1 H NMR，13 C NMR光谱合成，并在三种情况下通过单晶X射线衍射分析进行了表征。最有效的化合物9在对三种不同的人类癌细胞系（MCF-7，Hela和HepG2）没有明显的细胞毒性的情况下，它具有出色的抗侵袭和抗转移特性。进一步的蛋白质水平研究表明，复合物的抗转移活性可能是由于E-钙粘蛋白表达的增加和波形蛋白的表达减少所致。
• Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones
  作者：Araceli Rebollar、Rafael Bautista、Rsuini Gutiérrez、Carlos Espinoza‑Hicks、Aarón Mendieta、Daniel Zárate-Zárate、Eder Martínez-Mora、Ehecatl Labarrios-Morán、Miguel Vázquez、Francisco Delgado、Joaquín Tamariz

  DOI：10.21577/0103-5053.20210120

  日期：——

  applied without purification to the synthesis of 4-imidazolin-2-ones and 2-thiones, including chiral derivatives. The latter two series were obtained in high yields by a heteroannulation reaction of α-aminoketones with isocyanates and isothiocyanates, respectively. A double condensation of the α-aminoketones with two mol equivalents of the isocyanates produced a series of 4,5-dialkylN,3-diaryl-2-oxo-2

  在甲醇/盐酸中氢化α-氧肟酮生成α-氨基酮，未经纯化即可用于合成4-咪唑啉-2-酮和2-硫代咪唑啉，包括手性衍生物。后两个系列通过α-氨基酮与异氰酸酯和异硫氰酸酯的杂环化反应高产得到。α-氨基酮与两摩尔当量的异氰酸酯的双缩合产生了一系列4,5-二烷基N，3-二芳基-2-氧代-2，3-二氢-1H-咪唑-1-羧酰胺。与异硫氰酸酯反应，单一缩合反应产生了一系列4,5-二烷基-1-芳基-1H-咪唑-2（3H）-硫醇，其可通过与烷基卤化物烷基化反应高产得到相应的1-芳基-2-硫代烷基-1H-咪唑。
• C–C Bond Cleavage-Induced C- to N-Acyl Transfer for Synthesis of Amides
  作者：Su Eun Lee、Youngsoo Kim、Yong Ho Lee、Hee Nam Lim

  DOI：10.1021/acs.orglett.4c01154

  日期：2024.5.3

  A new approach for the preparation of amides was developed using C–C bond cleavage that initiates C- to N-acyl transfer, employing activated ketones as acylation reagents and amine nucleophiles. The reaction was operational under the coupling reagent system that is commonly utilized for peptide bond formations. The method enables practical preparation of amides using linear and cyclic ketone substrates

  开发了一种制备酰胺的新方法，使用 C-C 键断裂引发 C- 到 N- 酰基转移，采用活化酮作为酰化试剂和胺亲核试剂。该反应在常用于肽键形成的偶联试剂系统下进行。该方法使得能够在温和条件下使用线性和环状酮底物实际制备酰胺。
• Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries
  作者：Rsuini U. Gutiérrez、Araceli Rebollar、Rafael Bautista、Vanessa Pelayo、José Luis Várgas、Mabel M. Montenegro、Carlos Espinoza-Hicks、Francisco Ayala、Pablo M. Bernal、Cuauhtemoc Carrasco、L. Gerardo Zepeda、Francisco Delgado、Joaquín Tamariz

  DOI：10.1016/j.tetasy.2015.01.011

  日期：2015.2

  Functionalized alpha-oximinoketones with beta-alkoxy, beta-alkyl, and beta-sulfenyl groups were used as efficient synthons for the preparation of chiral 1-acyl-4-imidazolin-2-ones and 1-acylimidazolidin-2-ones. For the preparation of the former heterocycles, alpha-oximinoketones were transformed into their respective imidazole N-oxides by neutral treatment with a chiral triazine, followed by reaction with acetic or propionic anhydrides to furnish the desired chiral 1-acetyl- or 1-propionyl-4-imidazolin-2-ones in moderate overall yields. Upon palladium hydroxide-catalyzed hydrogenation, these series were converted into their corresponding 1-acylimidazolidin-2-ones in high diastereoisomeric ratios. Thus, these novel chiral 1-acetyl- and 1-propionyl-imidazolidin-2-ones were obtained with a variety of alkyl groups at the C-4 and C-5 positions of the heterocycle, through a three-step methodology, and can be applied as new potential chiral auxiliaries. (C) 2015 Elsevier Ltd. All rights reserved.