2,4-bis(4-methoxyphenyl)-2,4-diazaspiro[5.5]undecan-7-one

• 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: 2,4-bis(4-methoxyphenyl)-2,4-diazaspiro[5.5]undecan-7-one
• 英文别名: 2,4-Bis(4-methoxyphenyl)-2,4-diazaspiro[5.5]undecan-11-one
• 化学式: C₂₃H₂₈N₂O₃
• 分子量: 380.487
• InChiKey: IVPPWGPSSFUYQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-乙酰基环己酮 、 甲氧苯胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 3.17h， 以79%的产率得到2,4-bis(4-methoxyphenyl)-2,4-diazaspiro[5.5]undecan-7-one
  参考文献：
  名称：

  One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines

  摘要：

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.

  DOI：

  10.1055/s-0033-1339922

文献信息

• Metal free green protocol for the synthesis of bis-spiro piperidine and pyrimidine derivatives
  作者：Audumbar Patil、Rajashri Salunkhe

  DOI：10.1007/s11164-018-3310-7

  日期：2018.5

  one-pot three-component synthesis of bis-spiro piperidine and pyrimidine derivatives has been reported by performing the reaction of formaldehyde, aromatic aniline and 1,3-dicarbonyl compounds. This reaction was carried out at room temperature in 2,2,2-trifluoroethanol (TFE) as a recyclable reaction medium under the metal free condition. The strong hydrogen donor ability and acidic property of TFE plays

  摘要 据报道，通过甲醛，芳族苯胺和1,3-二羰基化合物的反应，可以高效地一锅三组分合成双螺哌啶和嘧啶衍生物。该反应在室温下在2,2,2-三氟乙醇（TFE）中作为可循环的反应介质在无金属条件下进行。TFE的强大的氢供体能力和酸性对加快反应速率和平稳引发反应起着关键作用。该方法的优点是反应条件温和，无需柱色谱纯化，产物收率高和TFE可回收利用。 图形概要
• Indium triflate catalyzed one-pot multicomponent synthesis of spiro-hexahydropyrimidines explained by multiple covalent bond formation
  作者：Anshu Dandia、Anuj K. Jain、Sonam Sharma

  DOI：10.1016/j.tetlet.2012.07.079

  日期：2012.9

  A mild, efficient, and expeditious method has been developed for the synthesis of spiro-hexahydropyrimidine derivatives via a three-component, one-pot cyclocondensation reaction of aromatic amines, formaldehyde, and cyclic ketones in 4-6 h using In(OTf)(3) as Lewis acid catalyst for the first time. The reaction involving creation of six new covalent bonds was efficiently promoted by 10 mol % In(OTf)(3) and the catalyst could be recovered easily after the reaction and reused without any loss of its catalytic activity. The advantageous features of this methodology are high atom-economy, operational simplicity, shorter reaction time, and easy handling. (c) 2012 Elsevier Ltd. All rights reserved.
• New Light on an Old Story:  Facile and Efficient Synthesis of 1,3-Diaryl-5-spirohexahydro- pyrimidines via a Six-Molecule, Three-Component Mannich-Type Reaction
  作者：Hai-Long Wei、Ze-Yi Yan、Yan-Ning Niu、Gao-Qiang Li、Yong-Min Liang

  DOI：10.1021/jo7016235

  日期：2007.10.1

  A facile and efficient synthesis of I,3-diaryl-5-spirohexahy-dropyrimidines via a one-pot condensation of anilines, formaldehyde, and cyclohexanones is reported. In this one-pot, three-component reaction, six molecules of reactants are involved and six new covalent bonds are generated. Bicyclic products are obtained from the starting materials in one pot using readily available starting materials and catalysts.
• One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines
  作者：Julia Stephanidou-Stephanatou、Constantinos Tsoleridis、Constantinos Neochoritis、Nicolaos Eleftheriadis、Arianna Tsiantou

  DOI：10.1055/s-0033-1339922

  日期：——

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.