1-(2-甲氧基苯基)戊-1-酮 | 20359-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-甲氧基苯基)戊-1-酮
• 英文名称: 1-(2-methoxyphenyl)pentan-1-one
• 英文别名: o-Methoxy-valerophenon
• CAS: 20359-54-0
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BDXUPRHNPQNYBK-UHFFFAOYSA-N

物化性质

• 沸点：
  82 °C(Press: 0.1 Torr)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧基苯基)戊-1-酮 在 盐酸 、 锌 作用下， 生成 1-甲氧基-2-戊基苯
  参考文献：
  名称：

  Condensations by Sodium. XXXVI. The Alkylation of Anisole and of o-Cresol Methyl Ether and the Composition of a Reacting Aggregate^1,2

  摘要：

  DOI：

  10.1021/ja01640a035
• 作为产物：
  描述：

  1-(2-methoxyphenyl)-1-pentanol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以1.26 g的产率得到1-(2-甲氧基苯基)戊-1-酮
  参考文献：
  名称：

  铑催化酮的脱氧和硼酸化：结合实验和理论研究

  摘要：

  已经开发了铑催化的酮与 B2pin2 的脱氧和硼酸化，从而有效地形成烯烃、乙烯基硼酸酯和乙烯基二硼酸酯。这些反应的特点是反应条件温和，底物范围广，官能团兼容性好。机理研究支持酮最初经过 Rh 催化脱氧以通过硼烯醇化物中间体得到烯烃，随后 Rh 催化的烯烃脱氢硼化导致乙烯基硼酸酯和二硼化产物的形成，这也得到 DFT 计算的支持。

  DOI：

  10.1021/jacs.0c07854

文献信息

• Reaction of aldehyde O-alkyl oxime with organometallic compounds
  作者：Shinichi Itsuno、Koji Miyazaki、Koichi Ito

  DOI：10.1016/s0040-4039(00)84709-7

  日期：1986.1

  Aldehyde O-alkyl oximes were converted into ketones with high yields when they were treated with alkyllithium compounds or Grignard reagents followed by hydrolysis. Amines as reductive alkylation products of aldehyde O-alkyl oximes were also obtained by BH3 reduction before hydrolysis.

  当用烷基锂化合物或格利雅试剂进行处理，然后水解时，醛O-烷基肟被高产率地转化为酮。还通过在水解前通过BH 3还原获得作为醛基O-烷基肟的还原烷基化产物的胺。
• A CONVENIENT METHOD FOR THE DIRECT PREPARATION OF KETONES FROM 2-(6-(2-METHOXYETHYL)PYRIDYL)CARBOXYLATES AND ALKYL IODIDES BY USE OF ZINC DUST AND A CATALYTIC AMOUNT OF NICKEL DICHLORIDE
  作者：Makoto Onaka、Yoshio Matsuoka、Teruaki Mukaiyama

  DOI：10.1246/cl.1981.531

  日期：1981.4.5

  Treatment of 2-(6-(2-methoxyethyl)pyridyl) carboxylates with alkyl iodides in the presence of zinc dust and a catalytic amount of NiCl2 in DMF at 50 °C affords unsymmetrical ketones in good yields by a one-pot procedure.

  在锌粉和催化量的 NiCl2 的 DMF 存在下，在 50 °C 下用烷基碘处理 2-（6-（2-甲氧基乙基）吡啶基）羧酸酯，通过一锅法以良好的收率提供不对称酮。
• A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects
  作者：Simone Ghinato、Davide Territo、Andrea Maranzana、Vito Capriati、Marco Blangetti、Cristina Prandi

  DOI：10.1002/chem.202004840

  日期：2021.2.5

  We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the

  我们报道，脂肪族和（杂）芳族酰胺通过有机锂试剂的亲核酰基取代反应进行迅速（20 s反应时间），有效地进行，并且在环境温度和环境温度下，在对环境负责的环戊基甲基醚中具有广泛的底物范围进行化学选择性空气，以提供高达93％的产率的酮，并有效抑制臭名昭著的加成反应。详细的DFT计算和NMR研究支持了实验结果。事实证明，所描述的方法适用于规模扩大和可回收性协议。与在惰性气氛下进行的经典程序相反，这项工作为羧酸酰胺与有机锂的反应性发生深刻的范式转变奠定了基础，
• Nickel-Catalyzed Intermolecular Insertion of Aryl Iodides to Nitriles: A Novel Method to Synthesize Arylketones
  作者：Jen-Chieh Hsieh、Yen-Chung Chen、An-Yi Cheng、Hsiao-Chun Tseng

  DOI：10.1021/ol300153f

  日期：2012.3.2

  A novel procedure for the NiCl2(DME)/dppp/Zn system catalyzed intermolecular insertion of aryl iodides to nitriles was developed, which afforded variously substituted arylketone derivatives in moderate to good yields with tolerance of a wide variety of functional groups.
• Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
  作者：Alan R. Katritzky、Hengyuan Lang、Zuoquan Wang、Zhongxing Zhang、Huimin Song

  DOI：10.1021/jo00128a039

  日期：1995.11

  Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding alpha-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), alpha-hydroxyalkyl (12 and 13), alpha-aminoalkyl (14) and acyl(15) substituents.