syn-α-bromoacetophenone oxime | 17082-14-3

• 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: syn-α-bromoacetophenone oxime
• 英文别名: 2-bromo-1-phenylethanone oxime；syn-2-bromoacetophenone oxime；2-bromoacetophenone oxime；α-bromoacetophenone oxime；2-bromo-1-phenyl-ethanone-(E)-oxime；2-Brom-1-phenyl-aethanon-(E)-oxim；(NE)-N-(2-bromo-1-phenylethylidene)hydroxylamine
• CAS: 17082-14-3
• 化学式: C₈H₈BrNO
• 分子量: 214.062
• InChiKey: CPIZBNJPBHXWFN-NTMALXAHSA-N

物化性质

• 熔点：
  92 °C
• 沸点：
  296.8±23.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 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：

  syn-α-bromoacetophenone oxime 在 吡啶 作用下， 以 甲醇 为溶剂， 生成 anti-α--acetophenon-oxim-<4-methoxy-benzoat>
  参考文献：
  名称：

  反式和反式α-氨基酮肟衍生物的生产和构型测定

  摘要：

  已经与相应的苯甲酸酯和2，4-二硝基苯基醚一起制备了几种顺式和反式α-氨基苯乙酮肟。根据UV-和IR-吸收光谱及其形成铜络合物的能力，明确确定了它们的构型。-酮肟的酯，例如环己酮肟和苯乙酮肟的苯甲酸酯，很容易被N-溴代琥珀酰亚胺溴化在α位。

  DOI：

  10.1002/hlca.19620450723
• 作为产物：
  描述：

  2-溴苯乙酮 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 生成 syn-α-bromoacetophenone oxime
  参考文献：
  名称：

  Replacement of the Methylene of Dihydrochalcones with Oxygen: Synthesis and Biological Evaluation of 2-Phenoxyacetophenones

  摘要：

  With the aim of finding new bioactive compounds, a series of phenoxyacetophenone derivatives 2 were designed and synthesized as oxygen analogs of dihydrochalcones. Also, phenoxyacetophenones were converted to (Z)‐oxime derivatives 3 and their geometry were characterized by 1H‐NMR spectroscopy. The in vitro antifungal activity of compounds 2 and 3 was evaluated against Candida albicans, Candida glabrata, Saccharomyces cerevisiae, and Aspergillus niger using micro‐dilution method. In general, oxime derivative 3d containing 4‐fluorophenoxy moiety showed comparable or more potent antifungal activity (MICs = 15.63–31.25 μg/mL) with respect to the reference drug fluconazole against all tested yeasts. In addition, the antileishmanial activity of title compounds was determined against pormastigote form of Leishmania major. All compounds showed mild growth inhibitory activity against promastigotes. The most active compound was unsubstituted phenoxyacetophenone 2a (IC50 = 80 μg/mL). To anticipate the potential use as drugs, the target compounds were evaluated in their drug‐like properties. The in silico values of molecular descriptors for bioactive compounds 2a and 3d revealed that these compounds are within the range set by Lipinski’s ‘Rule of 5’ and show no violation of these rules. Moreover, bioactive compounds 2a and 3d are supposed to be non‐mutagenic and non‐tumorigenic, with no irritating or reproductive effects.

  DOI：

  10.1111/j.1747-0285.2012.01432.x

文献信息

• Synthesis of Highly Substituted Pyrroles via Nucleophilic Catalysis
  作者：Simbarashe Ngwerume、Jason E. Camp

  DOI：10.1021/jo1011448

  日期：2010.9.17

  tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermolecular addition of oximes to activated alkynes and thermal rearrangement of the in situ generated O-vinyl oximes to form pyrroles that contain a functional group handle at the C3/C4 position.

  描述了提供二，三和四取代吡咯的简明合成的亲核催化方法。这种区域选择性的一锅法依赖于在分子间加成肟到活化的炔烃上的亲核催化和原位生成的O-乙烯基肟的热重排形成吡咯，这些吡咯在C3 / C4位置上含有一个官能团。
• Synthesis of potential inhibitors of GTP-cyclohydrolase I: an efficient synthesis of 8-substituted 7-deazaguanines
  作者：Colin L. Gibson、Klaus Paulini、Colin J. Suckling

  DOI：10.1039/a608297a

  日期：——

  A novel two step synthesis of 8-substituted 7-deazaguanines is developed and involves the regioselective alkylation of pyrimidinones 1a and 1b with nitrosoalkenes derived from α-halo oximes followed by transoximation to give the 7-deazaguanines 6a–d in 41–65% overall yield

  开发了一种新颖的两步合成8-取代-7-脱氮鸟嘌呤的方法，该方法包括选择性烷基化嘧啶酮1a和1b与由α-卤代肟衍生的亚硝基烯烃的反应，随后进行转肟反应，以总产率41-65%得到7-脱氮鸟嘌呤6a-d。
• Reactivity of 1-arylnitrosoethylenes towards indole derivatives
  作者：Susana M. M. Lopes、Sandra C. C. Nunes、Cátia C. Caratão、Alberto A. C. C. Pais、Teresa M. V. D. Pinho e Melo

  DOI：10.1007/s00706-016-1763-1

  日期：2016.9

  1-(p-bromophenyl)nitrosoethylene and indole and its derivatives are similar to those observed for the reaction between this nitrosoalkene and pyrrole. However, the calculated energy of the theoretical Diels–Alder cycloadducts involving indole and pyrrole clearly suggests that the Diels–Alder reaction is privileged in the case of indole. Furthermore, in the case of the indole, the energy difference between

  摘要描述了1-芳基亚硝基烯烃对吲哚，1-甲基吲哚和3-甲基吲哚的反应性。与先前观察到的1-（对溴苯基）亚硝基亚乙基对吡咯的化学行为相反，所研究的杂二烯与吲哚和1-甲基吲哚反应，通过杂Diels-Alder反应生成E-肟。与3-甲基吲哚的反应也通过环加成反应进行，得到相应的1，2-恶嗪。在DFT级别的量子化学计算表明，与1-（p-溴苯基）亚硝基亚乙基和吲哚及其衍生物与亚硝基链烯和吡咯之间的反应相似。但是，理论上涉及吲哚和吡咯的Diels-Alder环加合物的计算能量清楚地表明，在吲哚的情况下，Diels-Alder反应具有特权。此外，在吲哚的情况下，反应物和产物之间的能量差明显有利于实验观察到的区域化学。 图形概要
• [EN] A DEVELOPING AGENT PRECURSOR FOR LASER MARKABLE COMPOSITIONS<br/>[FR] PRÉCURSEUR D'AGENT DE DÉVELOPPEMENT POUR COMPOSITIONS POUVANT ÊTRE MARQUÉES AU LASER
  申请人：AGFA NV

  公开号：WO2018228857A1

  公开（公告）日：2018-12-20

  The invention relates to novel laser markable compositions comprising developing agent precursors according to formula (I).

  该发明涉及具有根据式(I)的显影剂前体的新型可激光标记组合物。
• Novel beta-oximinoalkylphosphonic acid ester derivatives and method of preparation
  申请人：ALLIED CORPORATION

  公开号：EP0086936A1

  公开（公告）日：1983-08-31

  Novel β-oximinoalkylphosphonic acid ester derivatives of general formula 8 are prepared from the corresponding α-halo oxime A: wherein R' is a substituent selected from the group consisting of H and C1-C20 alkyl, cycloalkyl and aryl substituents; R2 is a substituent selected from the group consisting of H and C, to C20 linear alkyl and aryl substituents; R3 is a substituent selected from the group consisting of H and C, to C20 alkyl, cycloalkyl, 1-alkoxy alkyl, aryl, acyl, N-substituted carbamoyl, N,N-disubstituted carbamoyl and nitrogen-, oxygen-, sulfur-, and phosphorus-containing heterocyclic substituents; R4 is an alkyl substituent of C, to C20 and X is a substituent selected from the group consisting of Cl, Br, I. In a specific reaction, the a-halo oxime derivative is dissolved in an excess of trialkyl phosphite, greater than 3 molar equivalents is preferred. The preference for the a-halogen atom follows the order I>>Br>>Cl which parallels their rate of reaction with trialkyl phosphite. The acceptable temperature range includes ambient conditions. The reaction can be run in various solvents including tetrahydrofuran, toluene and acetonitrile.

  由相应的α-卤代肟 A 制备通式 8 的新型β-氧亚氨基烷基膦酸酯衍生物： 其中 R' 是选自 H 和 C1-C20 烷基、环烷基和芳基取代基组成的取代基； R2 是选自 H 和 C1-C20 直链烷基和芳基取代基组成的取代基； R3 是选自 H 和 C 至 C20 直链烷基、环烷基、1-烷氧基烷基、芳基、酰基、N-取代氨基甲酰基、N,N-二取代氨基甲酰基和含氮、氧、硫和磷的杂环取代基组成的取代基； R4 是 C 至 C20 的烷基取代基，以及 X 是选自 Cl、Br、I. 在特定的反应中，a-卤代肟衍生物溶解在过量的三烷基亚磷酸酯中，优选大于 3 摩尔当量。a-卤素原子的优先选择顺序为 I>>Br>>Cl，这与它们与亚磷酸三烷基酯的反应速度相一致。可接受的温度范围包括环境条件。反应可在四氢呋喃、甲苯和乙腈等多种溶剂中进行。