(E)-1-phenylethanone oxime | 10341-75-0

• 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: (E)-1-phenylethanone oxime
• 英文别名: acetophenone oxime；(E)-1-phenylethan-1-one oxime；(E)-acetophenone oxime；1-(phenyl)ethanone oxime；acetophenone (E)-oxime；α-methylbenzaldehydeoxime trichloroacrylate；(NE)-N-(1-phenylethylidene)hydroxylamine
• CAS: 10341-75-0
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: JHNRZXQVBKRYKN-VQHVLOKHSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  245.0±9.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 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

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  (E)-1-phenylethanone oxime 在 去甲麻黄碱 、 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-(-)- α-甲基苄胺
  参考文献：
  名称：

  Asymmetric reduction of ketoxime derivatives and N-alkylketimines with borane–oxazaborolidine adducts

  摘要：

  Oxime ethers of acetophenone, isopropyl methyl ketone, and tert-butyl methyl ketone were reduced to the corresponding hydroxylamine ethers of 45-94% ee with borane-oxazaborolidine 1 derived from (-)-norephedrine. A one-pot reduction of acetophenone oxime with 1 to 1-phenylethylhydroxylamine of 87% ee is described. The reduction of 6-methyl-2,3,4,5-tetrahydropyridine and N-methylimines of the above mentioned ketones with borane-B-methyloxazaborolidine adduct 2, derived from (-)-diphenylprolinol, gave the corresponding amines of 40-74% ee. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00314-8
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 [(nBu₃Sn)₂WO₄] 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以78%的产率得到(E)-1-phenylethanone oxime
  参考文献：
  名称：

  有机锡-氧钨酸配位聚合物：胺类选择性氧化的有效催化剂

  摘要：

  摘要 有机金属配位聚合物[( n Bu 3 Sn) 2 WO 4 ]分别催化仲胺和伯胺选择性氧化为硝酮和肟。发现该催化剂可重复使用五个催化循环而没有任何明显的活性损失。在优化的反应条件下[4 mol% 催化剂，3-4 当量过氧化氢（30 wt%，水溶液），甲醇作为溶剂，rt]，可以高效地获得相应的硝酮和肟。

  DOI：

  10.1016/j.crci.2014.06.005

文献信息

• HERBICIDAL AND FUNGICIDAL 5-OXY-SUBSTITUTED 3-PHENYLISOXAZOLINE-5-CARBOXAMIDES AND 5-OXY-SUBSTITUTED 3-PHENYLISOXAZOLINE-5-THIOAMIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150245616A1

  公开（公告）日：2015-09-03

  Herbicidally and fungicidally active 5-oxy-substituted 3-phenylisoxazoline-5-carboxamides and 5-oxy-substituted 3-phenylisoxazoline-5-thioamides of the formula (I) are described. In this formula (I), X, X 2 to X 6 , R 1 to R 4 are radicals such as hydrogen, halogen and organic radicals such as substituted alkyl. A is a bond or a divalent unit. Y is a chalcogen.

  具有除草和杀菌活性的5-氧代取代的3-苯基异噁唑啉-5-羧酰胺和5-氧代取代的3-苯基异噁唑啉-5-硫酰胺的化合物如下式（I）所述。 在这个式子（I）中，X，X2至X6，R1至R4是氢、卤素和有机基团，如取代烷基等。A是一个键或二价基团。Y是硫族元素。
• Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate
  作者：Kotaro Ishihara、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tetlet.2019.04.014

  日期：2019.5

  A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method

  开发了一种新的方法，该方法通过使用贝克曼重排从酮肟中立体异构合成1,5-二取代的四唑，同时使用了叠氮基磷酸二苯酯（DPPA）作为肟的活化剂和叠氮化物的来源。具有排他性的跨基团迁移并且没有酮肟的EZ异构化，将各种酮肟转化为相应的1，5-二取代的四唑。该方法无需使用有毒或易爆的叠氮化试剂即可制备1,5-二取代的四唑。
• <i>m</i>-CPBA Mediated Metal Free, Rapid Oxidation of Aliphatic Amines to Oximes
  作者：Vilas V. Patil、Eknath M. Gayakwad、Ganapati S. Shankarling

  DOI：10.1021/acs.joc.5b01740

  日期：2016.2.5

  An efficient, rapid oxidation of various aliphatic amines to oximes using m-CPBA as an oxidant in ethyl acetate is described. High conversion (100%) with >90% oxime selectivity is achieved at room temperature under catalyst-free conditions. Mild reaction conditions along with an easy work up procedure offer lower byproduct formation and high selectivity for oximes in good yield and purity.

  一种高效，快速的各种脂族胺的使用肟氧化米-CPBA如乙酸乙酯中的氧化剂进行说明。在室温下在无催化剂条件下实现了高转化率（100％）和> 90％的肟选择性。温和的反应条件以及简便的后处理步骤可降低副产物的生成，并以较高的收率和纯度提供对肟的高选择性。
• Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation
  作者：Daniel Méndez-Sánchez、Iván Lavandera、Vicente Gotor、Vicente Gotor-Fernández

  DOI：10.1039/c7ob00374a

  日期：——

  chemoenzymatic process. This strategy is based on a two-step sequence developed in one-pot at 30 °C and atmospheric pressure. First, the formation of a reactive peracid intermediate occurs by means of a lipase-catalysed perhydrolysis reaction, and then this peracid acts as a chemical oxidising agent of the amines. A total of nine ketoximes were isolated in high purity after a simple extraction protocol (90–98%

  已经通过化学酶促方法描述了苄胺向相应肟的有效转化。此策略基于在30°C和大气压下在一锅中开发的两步顺序。首先，借助于脂肪酶催化的过水解反应发生反应性过酸中间体的形成，然后该过酸充当胺的化学氧化剂。通过简单的提取操作，总共可以分离出九种高纯度的酮肟（分离产率为90-98％），而对于11种合成的醛肟，则需要进一步的柱色谱纯化（分离产率为71-82％）。在所有情况下，均具有出色的选择性，为胺在短反应时间内（1小时）的氧化提供了一种实用的方法。电子因子值。
• PROCESS FOR THE PREPARATION OF NITRO COMPOUNDS AND METHOD FOR THE REMOVAL OF NITROGEN DIOXIDE
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1099684A1

  公开（公告）日：2001-05-16

  In the invented process for producing a nitro compound, an organic substrate and nitrogen dioxide are reacted in the presence of oxygen or are reacted in a molar ratio of nitrogen dioxide to the organic substrate of less than 1 to yield a corresponding nitro compound. The reaction may be performed in the presence of N-hydroxyphthalimide or other imide compounds. Such organic substrates include (a) aliphatic hydrocarbons, (b) alicyclic hydrocarbons, (c) non-aromatic heterocyclic compounds each having a carbon atom on a ring, which carbon atom is bonded to a hydrogen atom, (d) compounds each having a carbon-hydrogen bond at the adjacent position to an aromatic ring, and (e) compounds each having a carbon-hydrogen bond at the adjacent position to a carbonyl group. This process can efficiently nitrate an organic substrate even under relatively mild conditions.

  在制备硝基化合物的发明过程中，有机底物和二氧化氮在氧气存在下反应，或者在二氧化氮与有机底物的摩尔比小于1的情况下反应，以产生相应的硝基化合物。该反应可以在N-羟基邻苯二甲酰亚胺或其他亚酰胺化合物存在下进行。这样的有机底物包括(a) 脂肪烃，(b) 脂环烃，(c) 非芳香杂环化合物，每个环上的碳原子与氢原子相结合，(d) 每个化合物在芳香环旁边位置具有碳氢键，以及(e) 每个化合物在酮基旁边位置具有碳氢键。这个过程可以在相对温和的条件下有效地对有机底物进行硝化。

表征谱图