phenylacetaldehyde O-methyloxime | 117210-66-9

• 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: phenylacetaldehyde O-methyloxime
• 英文别名: Phenylacetaldehyde, O-methyloxime, (E)；N-methoxy-2-phenylethanimine
• CAS: 117210-66-9
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: NICHQMGWWYWONX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenylacetaldehyde O-methyloxime 在 sodium dithionite 作用下， 以 1,4-二氧六环 为溶剂， 生成 苯乙腈
  参考文献：
  名称：

  用卟啉铁重建肌红蛋白产生催化活性增强的人工醛肟脱水酶

  摘要：

  生物催化醛肟脱水是在环境反应条件下不使用剧毒氰化物合成腈的最有效方法之一。同时，底物范围也存在限制。为了克服这些限制并进一步扩大这种生物催化反应的范围，我们正在开发一种基于血红素蛋白重构的具有增强醛肟脱水活性的人造金属酶。用铁卟啉辅因子 (rMb(FePc)) 重构的工程肌红蛋白对多种醛肟的脱水具有极高的催化活性。脱水反应的总转换数达到最大值9300。此外，rMb(FePc)被发现可以促进反应性较低的O-烷基醛肟的脱醇，而这些O-烷基醛肟在天然酶催化反应中不被接受为底物。一系列机械实验清楚地揭示了底物和活性位点远端 His/Ser 残基之间氢键的重要性。这些机制见解进一步激励我们对 rMb(FePc) 进行基于合理机制的工程，从而产生改进的 rMb(FePc) 变体，其活性比未突变的重组肌红蛋白催化剂高 24 倍。

  DOI：

  10.1021/acscatal.4c03220
• 作为产物：
  描述：

  N-methoxyphenethylamine 在 次氯酸叔丁酯 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以52%的产率得到phenylacetaldehyde O-methyloxime
  参考文献：
  名称：

  Electrophilic aromatic substitution with N-methoxy-N-acylnitrenium ions generated from N-chloro-N-methoxy amides: syntheses of nitrogen heterocyclic compounds bearing a N-methoxy amide group

  摘要：

  DOI：

  10.1021/jo00275a027

文献信息

• Stereoselective Synthesis of Quaternary Center Bearing Azetines and Their β-Amino Acid Derivatives
  作者：Christopher J. MacNevin、Rhonda L. Moore、Dennis C. Liotta

  DOI：10.1021/jo7018202

  日期：2008.2.1

  We describe here the use of a stable, four-membered azetine heterocycle for the preparation of highly substituted β-amino acid derivatives. Imidazolidinone chiral auxiliaries were found to eliminate a competitive reaction pathway that had been present under previously reported conditions for azetine synthesis. The ephedrine derived imidazolidin-2-one 21 was allowed to react as its chlorotitanium enolate

  我们在这里描述了稳定的四元氮杂环丁烷杂环在制备高度取代的β-氨基酸衍生物中的用途。发现咪唑烷酮手性助剂消除了在先前报道的氮杂环丁烷合成条件下已经存在的竞争性反应途径。使麻黄碱衍生的咪唑烷基-2-酮21在优化的条件下，以其氯钛酸烯醇酯与O-甲基或-苄基肟反应，以克为单位更好地接触沸腾。还发现了这些氮杂环丁烷在完全非对映异构控制下进行烷基化，从而提供了一个四元中心。随后的苯甲酰氯开环和辅助裂解提供相应的β2,2,3-氨基羰基衍生物的收率很高。
• Phenylacetaldehyde <i>O</i>-Methyloxime:  A Volatile Compound Produced by Grapefruit Leaves Infected with the Citrus Canker Pathogen, <i>Xanthomonas axonopodis</i> pv. <i>citri</i>
  作者：Aijun Zhang、John S. Hartung

  DOI：10.1021/jf050533x

  日期：2005.6.1

  An aldehyde oxime amethyl ether, phenylacetalclehyde O-methyloxime, was detected using solid-phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS) in the headspace above grapefruit leaves infected with Xanthomonas axonopodis pv. citri, the causal agent of citrus bacterial canker disease (CBCD). This disease is a major phytosanitary concern, and an eradication campaign against it is currently underway in Florida. Phenylacetalclehyde O-methyloxime has been reported to be produced by other plants and fragrant flowers, but it was not observed in the headspace above uninfected grapefruit leaves, the pathogenic bacterium X. axonopodis pv. citri itself, or grapefruit leaves infected with another closely related bacterial pathogen, X axonopodis pv. citrumelo, which causes citrus bacterial spot, a disease of no phytosanitary significance. It was also not detected from CBCD infected fruits, including orange, lemon, grapefruit, and lime. We conclude that phenylacetalclehyde O-methyloxime may potentially be used to identify CBCD infestations. However, more intensive studies will be required to fully evaluate the potential of phenylacetalclehyde O-methyloxime as a diagnostic compound for CBCD. Using SPME and GC-MS to measure phenylacetaldehyde O-methyloxime may provide an easy and feasible tool to complement current methods used to detect X axonopodis pv. citri in environmental samples.