1-(phenylglyoxylyl)-4-benzylpiperidine | 1281955-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(phenylglyoxylyl)-4-benzylpiperidine
• 英文别名: 1-(4-benzylpiperidin-1-yl)-2-phenylethane-1,2-dione
• CAS: 1281955-15-4
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: ZQQONOBCXABRNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  453.0±28.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙基苯 在 吡啶 、 N-羟基邻苯二甲酰亚胺 、 tetrabutylammonium tetrafluoroborate 、 氧气 、 四丁基碘化铵 作用下， 以 2,2,2-三氟乙醇 、 乙腈 为溶剂， 生成 1-(phenylglyoxylyl)-4-benzylpiperidine
  参考文献：
  名称：

  芳烃的选择性电化学氧化及单/多羰基化合物的制备

  摘要：

  在温和条件下开发了选择性电化学氧化。凭借这种电化学氧化，可以从不同的芳烃以中等至优异的产率和选择性制备各种单羰基和多羰基化合物。生成的羰基化合物可以在一锅反应中进一步转化为α-酮酰胺、高烯丙醇和肟。特别是，在单锅连续电解中制备了一系列 α-酮酰胺。机理研究表明，2,2,2-trifluoroethan-1-ol (TFE) 可以与催化剂物种相互作用并生成相应的氢键配合物，以提高电化学氧化性能。

  DOI：

  10.1007/s11426-021-1061-x

文献信息

• SeO2 mediated efficient synthesis of amides and α-ketoamides of secondary amines with wide substrate scope
  作者：Samdarshi Meena、Rohit Singh、Ram A. Vishwakarma、Mushtaq A. Aga、Shreyans K. Jain

  DOI：10.1016/j.tetlet.2016.06.129

  日期：2016.8

  SeO2 mediated oxidative amidation of acetophenones, phenylacetylenes, and phenylacetaldehydes to α-ketoamides and aldehydes to amides is reported. Amidation selectively proceeds with secondary amines. α-Ketoamide derivatives of natural products 16-dehydropregnenolone acetate (8), pregnenolone acetate (10), and progesterone (11) were synthesized.

  的SeO 2苯乙酮，phenylacetylenes，和α酮酰胺和醛酰胺phenylacetaldehydes的介导的氧化的酰胺化被报告。酰胺化选择性地与仲胺进行。合成了天然产物乙酸16-脱氢孕烯醇酮（8），乙酸孕烯醇酮（10）和孕酮（11）的α-酮酰胺衍生物。
• Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines
  作者：Arthur Y. Shaw、Christine R. Denning、Christopher Hulme

  DOI：10.1016/j.tetlet.2012.05.136

  日期：2012.8

  A facile and expeditious synthetic approach for the synthesis of alpha-ketoamides 3 is described. A series of alpha-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of alpha-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2. (C) 2012 Elsevier Ltd. All rights reserved.
• Benzoylformamides as new photocaged bases for photo-latent anion polymerization
  作者：Ming-Hui He、Mei-Lin Su、Zhao-Hui Yu、Guang-Xue Chen、Zhao-Hua Zeng、Jian-Wen Yang

  DOI：10.1016/j.cclet.2014.10.002

  日期：2015.1

  Benzoylformamide (BFA) derivatives are proposed as new photocaged bases with good solubility in epoxy resin. Initially their structures were confirmed by H-1 NMR,C-13 NMR, and elemental analysis. Next, we detail their thermal stability, solubility behavior, and photolysis products. Furthermore, the model photo-latent anion polymerization (AP) of epoxide system in the presence of BFA-dBA (N,N-dibenzyl-2-oxo-2-phenylacetamide) as a photocaged base has been investigated, and excellent photopolymerization profile is obtained. (C) 2014 Jian-Wen Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.
• Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds
  作者：Zhibin Li、Yan Zhang、Kuiliang Li、Zhenghong Zhou、Zhenggen Zha、Zhiyong Wang

  DOI：10.1007/s11426-021-1061-x

  日期：2021.12

  A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction

  在温和条件下开发了选择性电化学氧化。凭借这种电化学氧化，可以从不同的芳烃以中等至优异的产率和选择性制备各种单羰基和多羰基化合物。生成的羰基化合物可以在一锅反应中进一步转化为α-酮酰胺、高烯丙醇和肟。特别是，在单锅连续电解中制备了一系列 α-酮酰胺。机理研究表明，2,2,2-trifluoroethan-1-ol (TFE) 可以与催化剂物种相互作用并生成相应的氢键配合物，以提高电化学氧化性能。