3-benzyl-4-pyrimidone | 6146-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-benzyl-4-pyrimidone
• 英文别名: 3-benzylpyrimidin-4(3H)-one；3-Benzylpyrimidin-4-one
• CAS: 6146-23-2
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: QIKVSMDVDHTJRF-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  328.4±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-4-pyrimidone 在 劳森试剂 、 dimethyloxosulfonium methylide 、 水 作用下， 反应 0.5h， 生成 3-benzylpyrimidine-4-thione
  参考文献：
  名称：

  Jones, Gurnos; Tonkinson, Daryl J.; Hayes, Peter C., Journal of the Chemical Society. Perkin transactions I, 1983, # 11, p. 2645 - 2648

  摘要：

  DOI：
• 作为产物：
  描述：

  4-benzyl-2,4-diazabicyclo<4.1.0>hept-2-en-5-one 生成 3-benzyl-4-pyrimidone
  参考文献：
  名称：

  Jones, Gurnos; Tonkinson, Daryl J.; Hayes, Peter C., Journal of the Chemical Society. Perkin transactions I, 1983, # 11, p. 2645 - 2648

  摘要：

  DOI：

文献信息

• Reductive Synthesis of Aminal Radicals for Carbon–Carbon Bond Formation
  作者：David A. Schiedler、Yi Lu、Christopher M. Beaudry

  DOI：10.1021/ol500024q

  日期：2014.2.21

  Aminal radicals were generated by reduction of the corresponding amidine or amidinium ion. The intermediate radicals participate in C–C bond-forming reactions to produce fully substituted aminal stereocenters. No toxic additives or reagents are required. More than 30 substrate combinations are reported, and chemical yields are as high as 99%.

  通过还原相应的idine或am离子可生成氨基自由基。中间基团参与C–C键形成反应，以产生完全取代的氨基立体中心。不需要有毒的添加剂或试剂。据报道有30多种底物组合，化学收率高达99％。
• The development of carbon–carbon bond forming reactions of aminal radicals
  作者：David A. Schiedler、Jessica K. Vellucci、Yi Lu、Christopher M. Beaudry

  DOI：10.1016/j.tet.2014.12.067

  日期：2015.3

  Aminal radicals were generated and used in synthetic reactions for the first time. Aminal radicals are formed from aminals by radical translocation using AIBN and a stoichiometric hydrogen atom donor, or by SmI2 reduction of N-acyl amidines or amidinium ions in the presence of a proton source. Aminal radicals were found to participate in inter- and intramolecular C–C bond forming reactions with electron

  首次产生了氨基自由基，并将其用于合成反应中。通过使用AIBN和化学计量的氢原子供体的自由基易位，或通过在质子源存在下SmI 2还原N-酰基am或am离子，由氨基缩醛形成氨基自由基。发现氨基自由基参与与电子不足的烯烃的分子间和分子内CC键形成反应。化学收率高达99％。
• Manganese‐Promoted Regioselective Direct <i>C3</i> ‐Phosphinoylation of 2‐Pyridones
  作者：Tanakorn Kittikool、Kunita Phakdeeyothin、Teera Chantarojsiri、Sirilata Yotphan

  DOI：10.1002/ejoc.202100336

  日期：2021.6.7

  A Manganese-promoted direct oxidative C−P bond formation between 2-pyridones and secondary phosphine oxides has been developed. The reported protocol proceeds under mild reaction conditions, and the C3-phosphinoylation is proposed to take place under a radical process in the presence of substoichiometric amount of Mn(II).

  已开发出锰促进的 2-吡啶酮和二级氧化膦之间的直接氧化 C-P 键形成。所报道的方案在温和的反应条件下进行，C3-膦酰化被建议在亚化学计量量的 Mn(II) 存在下在自由基过程中进行。
• Ortho-Directed Palladium-Catalyzed Direct C–H Functionalization of 3-Picolinyl- and 3-(2-Cyanoethyl)pyrimidin-4(3H)-ones with Aryl Halides
  作者：Christine Baudequin、Laurent Bischoff、Christophe Hoarau、Sandra Collado Ruiz、Mickaël Muselli、Steven Frippiat、Thierno Mamoudou Diallo、Anissa Mohamed-Cherif、Vincent Levacher

  DOI：10.1055/s-0040-1707523

  日期：2020.7

  The ortho-directed palladium-catalyzed direct C–H arylation of 3-picolinylpyrimidin-4-one was achieved by using various aryl halides. The method was extended to C–H arylation of pyrimidin-4-ones containing a methoxy group and an aryl group at the C5 site. The 2-cyanoethyl substituent was also evaluated as an ortho-directing group. The method gives access to novel N-substituted 2-aryl or 2,5-diaryl

  通过使用各种芳基卤化物，实现了 3-吡啶甲基嘧啶-4-one 的邻位钯催化直接 C-H 芳基化。该方法扩展到在 C5 位点含有甲氧基和芳基的嘧啶-4-酮的 C-H 芳基化。2-氰乙基取代基也被评估为邻位导向基团。该方法可以获得新的 N-取代的 2-芳基或 2,5-二芳基嘧啶-4-酮。还研究了吡啶甲基的标准三步脱保护序列。
• Fe nano particles mediated C–N bond-forming reaction: Regioselective synthesis of 3-[(2-chloroquinolin-3-yl)methyl]pyrimidin-4(3H)ones
  作者：Selvaraj Mohana Roopan、Fazlur Rahman Nawaz Khan、Badal Kumar Mandal

  DOI：10.1016/j.tetlet.2010.02.128

  日期：2010.4

  An efficient and regioselective N-alkylation of 4(3H)-pyrimidone with various electrophiles in the presence of Fe nano particle is reported. The catalyst initiates N-alkylation of amides by alkyl chlorides. The reaction of equimolar 4(3H)-pyrimidone and 2-chloro-3-(chloromethyl)quinolines in the presence of KOH and Fe nano particle (5 mol %) m DMSO solution under reflux condition formed 3-[(2-chloroquinolin-3-yl]methyppyrimiclin-4(3H)ones. (C) 2010 Elsevier Ltd. All rights reserved.