2-(hydroxyimino)-1-(4-methoxyphenyl)propan-1-one | 5344-83-2

• 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-(hydroxyimino)-1-(4-methoxyphenyl)propan-1-one
• 英文别名: 2-Hydroxyimino-1-(4-methoxyphenyl)propan-1-one
• CAS: 5344-83-2
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: HSDNQULSFCKMAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(hydroxyimino)-1-(4-methoxyphenyl)propan-1-one 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 二乙胺基三氟化硫 、 Brettphos palladacycle 作用下， 以 二氯甲烷 、 均三甲苯 为溶剂， 反应 16.17h， 生成 2-(4-甲氧基苯基)-喹啉
  参考文献：
  名称：

  通过DAST介导的活化酮的氟化CC键裂解，合成酰基氟。

  摘要：

  通过将活化的酮识别为起始原料，开发了一种制备酰基氟的新方法。与先前报道的使用羧酸作为底物的方法相比，该方法提供了不同的范围。通过简单地将二乙基氨基三氟化硫（DAST）衍生物添加到α-肟基酮中，成功地证明了推拉驱动式C-C键断裂的有效假设。设计的反应系统可导致高效且化学选择性的反应。酮的广泛可用性允许使用一系列合成有用的芳酰基和脂族酰基氟，包括那些含有手性骨架的氟。该方法是温和的，快速的，可扩展的，并且可能一站式操作。

  DOI：

  10.1021/acs.orglett.0c02603
• 作为产物：
  描述：

  1-[(4-甲氧基)-苯基]-1,2-丙二酮 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以71%的产率得到2-(hydroxyimino)-1-(4-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2015.01.011

文献信息

• Visible Light Irradiation of Acyl Oxime Esters and Styrenes Efficiently Constructs β-Carbonyl Imides by a Scission and Four-Component Reassembly Process
  作者：Yuan-Yuan Cheng、Tao Lei、Longlong Su、Xiuwei Fan、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.orglett.9b03409

  日期：2019.11.1

  Acyl radical triggered difunctionalizations of aryl olefins have been realized using oxime ester as the acyl precursor for the first time. Irradiation of fac-Ir(ppy)3 and oxime ester by visible light caused scission into three components, which recombined with olefins to yield significant β-carbonyl imides showing good functional group tolerance and high atom economy. Control experiments as well as

  首次使用肟酯作为酰基前体，实现了芳基烯烃的酰基自由基引发的双官能化。用可见光照射fac-Ir（ppy）3和肟酯会导致分裂成三个组分，这些组分与烯烃重新结合，生成显着的β-羰基酰亚胺，具有良好的官能团耐受性和高原子经济性。对照实验以及光谱和电化学研究表明，在溶剂交换的帮助下，肟酯可有效地分子重组为苯乙烯。
• Chelator compositions comprising oxime compounds
  申请人：The Procter & Gamble Company

  公开号：US05364617A1

  公开（公告）日：1994-11-15

  The present invention involves photoprotective compositions which are useful for topical application to prevent damage to skin caused by acute or chronic exposure to ultraviolet light comprising chelating agents having the formula ##STR1## wherein --R.sup.1 and --R.sup.2 are independently selected from the group consisting of alkyl, aryl, and heteroaryl, or R.sup.1 and R.sup.2 may be covalently bonded together to form a cyclic alkyl; --M is selected from the group consisting of =0, =S, --SR.sup.4 and --OR.sup.4 (when --M is --OR.sup.4 or --SR.sup.4, there is a hydrogen bonded to the carbon to which --M is bonded); --R.sup.4 is selected from the group consisting of hydrogen, alkyl, aryl and heteroaryl; --R.sup.3 is selected from the group consisting of hydrogen, alkyl, aryl and heteroaryl; --R.sup.6 is selected from the group consisting of hydrogen alkyl, aryl and heteroaryl; and i is selected from the group consisting of one and zero. Methods for using such compositions to prevent damage to skin caused by acute or chronic exposure to ultraviolet light are al so involved.

  本发明涉及光保护组合物，适用于局部应用以预防由急性或慢性暴露于紫外线光引起的皮肤损伤，其包括具有以下结构的螯合剂：其中--R.sup.1和--R.sup.2分别来自于由烷基、芳基和杂环烷基组成的群，或者R.sup.1和R.sup.2可以共价结合在一起形成一个环状烷基；--M来自于由=0、=S、--SR.sup.4和--OR.sup.4组成的群（当--M为--OR.sup.4或--SR.sup.4时，与--M结合的碳上有氢键）；--R.sup.4来自于氢、烷基、芳基和杂环烷基组成的群；--R.sup.3来自于氢、烷基、芳基和杂环烷基组成的群；--R.sup.6来自于氢、烷基、芳基和杂环烷基组成的群；i来自于1和0的群。还涉及使用这类组合物的方法，以预防由急性或慢性暴露于紫外线光引起的皮肤损伤。
• Synthesis and Chemiluminescence of Coelenterazine (<i>Oplophorus</i>Luciferin) Analogues
  作者：Katsunori Teranishi、Toshio Goto

  DOI：10.1246/bcsj.63.3132

  日期：1990.11

  In the case of chemiluminescence of coelenterazine, effects of conformation rigidity of and hydrogen bonding with the emitter, coelenteramide, on the chemiluminescence efficiency have been examined with several coelenterazine analogues synthesized. Conformational rigidity has a light enhancing effect, whereas decreasing light yield was observed by hydrogen-bond formation with the emitter.

  就腔肠素的化学发光而言，我们利用合成的几种腔肠素类似物研究了发光体腔肠酰胺的构象刚性和氢键对化学发光效率的影响。构象刚性具有增光作用，而与发射体形成氢键则会降低光产率。
• Rh(III)-Catalyzed C–H Activation and [4+1+1] Sequential Cyclization Cascade to Give Highly Fused Indano[1,2-<i>b</i>]azirines
  作者：Fuqiang Zheng、Jianhui Zhou、Feifei Fang、Jiyuan Li、Jing Wang、Miao Zheng、Hong Liu、Yungen Xu、Yu Zhou

  DOI：10.1021/acs.orglett.2c02070

  日期：2022.8.12

  developed to construct the highly fused indano[1,2-b]azirine frameworks in good yields with a broad range of substrates under mild reaction conditions. More intriguingly, a [4+1+1] sequential annulation cascade is demonstrated for the first time in this reaction and opened a new reaction mode for α-keto oximes. These fused indano[1,2-b]azirine derivatives could also be further transformed into intriguing

  开发了 Rh(III) 催化的 α-酮肟的 C-H 活化和与重氮化合物的环化级联反应，以良好的产率构建高度稠合的茚满并[1,2- b ] 氮杂环丙烷骨架，并具有广泛的底物范围反应条件温和。更有趣的是，在该反应中首次证明了[4+1+1]顺序环化级联反应，并为α-酮肟开辟了新的反应模式。这些融合的茚满并[1,2- b ]氮丙啶衍生物也可以进一步转化为有趣的特权药物支架。
• Visible-Light-Promoted Intermolecular β-Acyl Difunctionalization of Alkenes via Oxidative Radical-Polar Crossover
  作者：Hao-Cong Li、Ke-Yuan Zhao、Yan Tan、Hao-Sen Wang、Wen-Shan Wang、Xiao-Lan Chen、Bing Yu

  DOI：10.1021/acs.orglett.3c03121

  日期：2023.11.17

  alkenes with acyl oxime esters and various nucleophiles was developed to achieve molecular complexity from readily available raw materials via oxidative radical-polar crossover. A variety of nucleophiles, including NH-sulfoximines, indoles, indazole, and trimethoxybenzene, were all effectively applicable to the sustainable reaction system. The novel synthetic strategy features mild reaction conditions

  开发了可见光诱导的烯烃与酰基肟酯和各种亲核试剂的β-酰基双官能化，以通过氧化自由基-极性交叉从容易获得的原材料中获得分子复杂性。多种亲核试剂，包括N H-亚磺酰亚胺、吲哚、吲唑和三甲氧基苯，都有效地适用于可持续反应体系。该新型合成策略具有反应条件温和、底物范围广（39个实例）、易于放大、以及优异的区域选择性等特点。