ethyl 2-(hydroxyimino)acetate

• 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: ethyl 2-(hydroxyimino)acetate
• 英文别名: ethyl 2-phenyl-2-hydroxyimino acetate；ethyl benzoylformate oxime；ethyl phenylglyoxylate oxime；α-Oximino-phenylessigsaeure-ethylester；Hydroxyimino-phenyl-essigsaeure-aethylester；hydroxyimino-phenyl-acetic acid ethyl ester；ethyl 2-(hydroxyimino)-2-phenylacetate；Phenylglyoxylsaeure-ethylester-oxim；Phenylglyoxalsaeureethylester-oxim；α-Oximino-phenylessigsaeure-aethylester；Phenylglyoxylsaeure-aethylester-oxim；Ethyl 2-hydroxyimino-2-phenylacetate；ethyl 2-hydroxyimino-2-phenylacetate
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: CYEGZACDKSTNKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 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：

  ethyl 2-(hydroxyimino)acetate 在 sodium tetrahydroborate 、 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-氨基-2-苯基乙酸
  参考文献：
  名称：

  使用硼氢化钠-雷尼镍系统还原肟、亚胺和腙中 CN 双键的简便方法

  摘要：

  摘要 开发了一种在 Raney Ni 催化下用硼氢化钠还原肟、亚胺和腙中 CN 双键的实用方法。反应在碱性水溶液中进行，经过简单的程序，以中等收率得到所需产物。该方法可用于合成更简单的脂肪族或芳香族胺及其类似物。图形概要

  DOI：

  10.1080/00397911.2011.562063
• 作为产物：
  描述：

  α-溴苯乙酸乙酯 在 乙醇 、 sodium nitrite 作用下， 生成 ethyl 2-(hydroxyimino)acetate
  参考文献：
  名称：

  The irradiation history of the Ghubara (L5) regolith breccia

  摘要：

  Abstract— We measured cosmic‐ray products—noble gases, radionuclides, thermoluminescence, and nuclear tracks—and trace element contents and mineralogy of samples of three orthogonal and mutually intersecting cores (41–46 cm long) of a 101.6 kg Ghubara individual (1958,805) at The Natural History Museum, London. The xenoliths, like the host, have high concentrations of trapped solar gases and are heavily shocked. While contents of noble gases and degree of shock‐loading in this individual and three others differ somewhat, the data indicate that Ghubara is a two‐generation regolith breccia. Contents of cosmogenic 26Al and 10Be and low track densities indicate that the Ghubara individuals were located more than 15 cm below the surface of an 85 cm meteoroid. Because of its large size, Ghubara's cosmic‐ray exposure age is poorly defined to be 15–20 Ma from cosmogenic nuclides. Ghubara's terrestrial age, based on 14C data, is 2–3 ka. Not only is Ghubara the first known case of a two‐generation regolith breccia on the macroscale, it also has a complicated thermal and irradiation history.

  DOI：

  10.1111/j.1945-5100.2002.tb00819.x

文献信息

• Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
  作者：Braja Gopal Das、Rajender Nallagonda、Dhananjay Dey、Prasanta Ghorai

  DOI：10.1002/chem.201501914

  日期：2015.9.1

  salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α‐amino esters, γ‐ and δ‐lactams, and isoindolinones have also been carried

  合成了空气/水分稳定，晶体和可储存的手性水杨基恶唑啉基氧化（V）配合物，并公开了其在氢化硅烷作为氢化物源的情况下催化不对称还原酮亚胺的催化应用。获得了广泛的底物范围，高收率和出色的对映选择性（最高99％）。此外，对映体纯α-氨基酯，γ-和δ-内酰胺以及异吲哚啉酮的合成也已使用该方法进行。最后，该方法已应用于具有药物相关性的合成靶标，例如R -（+）-沙丁胺碱和R -（+）-crispine A.
• Synthesis of 1,3,4-Oxadiazoles from Carboxylic Hydrazides and of 1,2-Oxazin-6-ones from α-(Hydroxyimino)carboxylic Esters with Keteneylidene Triphenylphosphorane
  作者：Jonas Löffler、Rainer Schobert

  DOI：10.1055/s-1997-766

  日期：1997.3

  In a one-pot procedure 1,3,4-oxadiazoles 8 are prepared from carboxylic hydrazides 2 and keteneylidene triphenylphosphorane 1 via an untypical intermolecular Wittig olefination of a carbamate type carbonyl group. Under similar conditions, reaction of 1 and α-(hydroxyimino) carboxylic esters 9 furnishes 1,2-oxazin-6-ones 11 by a different process including an intramolecular olefination step.

  在一锅法操作中，1,3,4-恶二唑8由羧酸酰肼2和烯酮叶立德三苯基膦1通过非典型的分子间维蒂希烯烃化反应制备，该反应涉及氨基甲酸酯型的羰基。在类似条件下，1与α-(羟基亚氨基)羧酸酯9反应，通过包括分子内烯烃化步骤的不同过程生成1,2-恶嗪-6-酮11。
• Enantioselective Reduction of Ketones and Imines Catalyzed by (CN-Box)ReV-Oxo Complexes
  作者：Kristine A. Nolin、Richard W. Ahn、Yusuke Kobayashi、Joshua J. Kennedy-Smith、F. Dean Toste

  DOI：10.1002/chem.201001164

  日期：2010.8.16

  application of chiral, non‐racemic ReV–oxo complexes to the enantioselective reduction of prochiral ketones is described. In addition to the enantioselective reduction of prochiral ketones, we report the application of these complexes to 1) a tandem Meyer–Schuster rearrangement/reduction to access enantioenriched allylic alcohols and 2) the enantioselective reduction of imines.

  描述了手性非外消旋 Re V - oxo 配合物在前手性酮的对映选择性还原中的开发和应用。除了前手性酮的对映选择性还原外，我们还报告了这些复合物在以下方面的应用：1）串联 Meyer-Schuster 重排/还原以获取对映体富集的烯丙醇和 2）亚胺的对映选择性还原。
• Nano-K₂CO₃: preparation, characterization and evaluation of reactive activities
  作者：Jun-Zhang Li、Shi-Ming Fan、Xuan-Fei Sun、Shouxin Liu

  DOI：10.1039/c5ra21597h

  日期：——

  Nano-K₂CO₃ shows higher basicity and can replace sodium (potassium) alkoxide to carry out monoalkylation and oximation of active methylene compounds.

  Nano-K2CO3显示出更高的碱性，并且可以替代钠（钾）烷氧化物来进行活性亚甲基化合物的单烷基化和氧化反应。
• Reaction of Acyl Oxime with Mercaptan
  作者：Rokuro Sudo、Akira Kaneda、Nobuo Furuoya

  DOI：10.1246/bcsj.42.1380

  日期：1969.5

  The acyl derivative of oxime, derived from a strong acid, is generally unstable. However, acyl oximes of the ethyl α-oximinoacetate derivative were prepared and were found to be more stable than ordinary acyl oxime. Acetyl, carbethoxy, benzoyl, and even tosyl ester were prepared, and their reactions with the mercaptide anion were investigated.

  由强酸衍生的肟的酰基衍生物通常是不稳定的。然而，制备了α-肟基乙酸乙酯衍生物的酰基肟，发现其比普通酰基肟更稳定。制备了乙酰基、羧基乙氧基、苯甲酰基，甚至甲苯磺酸酯，并研究了它们与硫醇盐阴离子的反应。