4-phenylbutanal oxime | 82543-06-4

• 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: 4-phenylbutanal oxime
• 英文别名: N-(4-phenylbutylidene)hydroxylamine
• CAS: 82543-06-4
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: UZFYCNRBFZQUGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  4-phenylbutanal oxime 在 碳酸氢钠 、 diborane(6) 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.25h， 生成 N-Hydroxy-N-(4-phenyl-butyl)-acetamide
  参考文献：
  名称：

  Synthesis and evaluation of N-(phenylalkyl)acetohydroxamic acids as potential substrates for N-arylhydroxamic acid N,O-acyltransferase

  摘要：

  N-(4-Phenylcyclohexyl)acetohydroxamic acid and a series of N-(phenylalkyl)acetohydroxamic acids were synthesized and evaluated as substrates for partially purified rat and hamster hepatic arylhydroxamic acid N,O-acyltransferase systems (AHAT). The compounds were assayed for their abilities to function as acetyl donors in the AHAT-mediated transacetylation of 4-aminoazobenzene and for their abilities to participate in the AHAT-mediated conversion of N-arylhydroxylamines to electrophilic intermediates that form methylthio adducts upon reaction with N-acetylmethionine. None of the newly synthesized compounds displayed significant activity in either of the assays. The results of this study indicate that acetohydroxamic acids that have the nitrogen atom of the hydroxamic acid group attached directly to aliphatic or cycloalkyl groups are not likely to serve as substrates or inhibitors of AHAT.

  DOI：

  10.1021/jm00352a018
• 作为产物：
  描述：

  4-苯基丁酸 在 dipotassium peroxodisulfate 、 三正丁基氢锡 、 silver nitrate 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 156.0h， 生成 4-phenylbutanal oxime
  参考文献：
  名称：

  通过自由基加成途径模块化合成碳取代的呋喃烷。基于“构建并报废”策略的脂肪族羧酸转化的有用工具。

  摘要：

  利用自由基化学，开发了在呋喃环上形成新的一般CC键的方法。通过利用呋喃喃的不稳定性，已证明了合成呋喃烷的多种转化。因此，这种发达的方法学不仅使呋喃喃的模块合成成为可能，而且使羧酸能够短时转化为各种官能团。

  DOI：

  10.1021/acs.orglett.0c00062

文献信息

• Purification and Characterization of Aldoxime Dehydratase of the Head Blight Fungus,<i>Fusarium graminearum</i>
  作者：Yasuo KATO、Yasuhisa ASANO

  DOI：10.1271/bbb.69.2254

  日期：2005.1

  Fungal aldoxime dehydratase (Oxd) of Fusarium graminearum MAFF305135 was purified and characterized for the first time from its overexpressing Escherichia coli transformant. The enzyme showed about 20% identity with known Oxds, and had similar enzymatic properties with nitrilase-linked Oxd from the Bacillus strain. It belongs to a group of phenylacetaldoxime dehydratases (EC 4.99.1.7), based on its substrate specificity and kinetic analysis.

  镰刀菌Fusarium graminearum MAFF305135的醛肟脱水酶（Oxd）首次从其过表达大肠杆菌转化子中纯化并表征。该酶与已知Oxd的相似性约为20%，并且具有与芽孢杆菌菌株中与腈水合酶连接的Oxd相似的酶学特性。基于其底物特异性和动力学分析，它属于苯乙醛肟脱水酶（EC 4.99.1.7）。
• A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH₂ OH) to Nitriles (RCN) Mediated by SO₂ F₂
  作者：Ying Jiang、Bing Sun、Wan-Yin Fang、Hua-Li Qin

  DOI：10.1002/ejoc.201900478

  日期：2019.6.2

  A new transition‐metal‐free one‐pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.

  在不引入“额外碳原子”的情况下，开发了一种新的无过渡金属的单锅级联工艺，用于将醇直接转化为腈。该方案允许将容易获得，廉价和丰富的醇转化为高价值的腈。
• Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles
  作者：Eiji Kobayashi、Hideo Togo

  DOI：10.1055/s-0039-1690102

  日期：2019.10

  Abstract Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc)2 in the presence of TEMPO, NH2OH, and then NCS, followed by reaction with alkynes in the presence of Et3N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive

  抽象的 通过在TEMPO，NH 2 OH和NCS的存在下依次用PhI（OAc）2连续处理，然后与炔烃反应，在一个锅中将各种伯醇顺利地转化成高产率的3-芳基-和3-烷基异恶唑。的Et存在下3 N.类似地，多种伯醇被顺利转化为3-芳基-和3- alkylpyrazoles以良好的收率以一锅煮的通过用岛（OAC）连续处理2在TEMPO，PhNHNH存在2，然后NCS和癸基甲基硫醚，然后在Et 3存在下与炔烃反应因此，3-芳基-和3-烷基异唑和3-芳基和3-烷基吡唑都可以在无过渡金属的条件下由易得的伯醇在一个罐中制备。 通过在TEMPO，NH 2 OH和NCS的存在下依次用PhI（OAc）2连续处理，然后与炔烃反应，在一个锅中将各种伯醇顺利地转化成高产率的3-芳基-和3-烷基异恶唑。的Et存在下3 N.类似地，多种伯醇被顺利转化为3-芳基-和3- alkylpyrazoles以良好的收率以一锅煮的
• Metal‐Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α‐Substituted Enantiomerically Enriched Nitriles
  作者：Margherita Pirola、Chiara Faverio、Manuel Orlandi、Maurizio Benaglia

  DOI：10.1002/chem.202100889

  日期：2021.7.16

  mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized

  已经开发了涉及硝基烷烃的无金属、温和且化学发散的转化。在优化的反应条件下，在三氯硅烷和叔胺的存在下，脂肪族硝基烷烃被选择性地转化为胺或腈。此外，当手性 β-取代硝基化合物反应时，立体中心的立体化学完整性得以保持，并在不损失对映体过量的情况下获得 α-官能化腈。该方法已成功应用于手性 β-氰基酯、α-芳基烷基腈和 TBS 保护的氰醇的合成，包括四种活性药物成分（布洛芬、tembamide、aegeline 和地诺巴胺）的直接前体。
• Amidyl Radical Directed Remote Allylation of Unactivated sp ³ C−H Bonds by Organic Photoredox Catalysis
  作者：Kui Wu、Lushun Wang、Sonivette Colón‐Rodríguez、Gerd‐Uwe Flechsig、Ting Wang

  DOI：10.1002/anie.201811004

  日期：2019.2.4

  visible‐light‐mediated allylation of unactivated sp3 C−H bonds is reported. The remote allylation was directed by the amidyl radical, which was generated by photocatalytic fragmentation of a pre‐functionalized amide precursor. Both aromatic and aliphatic amide derivatives could successfully deliver the remote C−H allylation products in good yields. A variety of electron deficient allyl sulfone systems could

  报道了未激活的sp 3 C-H键的可见光介导的烯丙基化的发展。远程烯丙基化是由酰胺基进行的，该酰胺基是由预官能化酰胺前体的光催化裂解生成的。芳香族和脂肪族酰胺衍生物均可成功地以高收率交付偏远的CH烯丙基化产物。多种缺电子的烯丙基砜系统可用作δ-碳自由基受体。