2,4-diphenyl-2,4-diazaspiro[5.5]undecan-7-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,4-diphenyl-2,4-diazaspiro[5.5]undecan-7-one
• 英文别名: 2,4-bis-phenyl-2,4-diazaspiro[5.5]undecan-7-one；2,4-Bis-phenyl-2,4-diazaspiro [5.5]undecane-7-one；2,4-diphenyl-2,4-diazaspiro[5.5]undecan-11-one
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: MFIMSMZJPZQLQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-乙酰基环己酮 、 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68%的产率得到2,4-diphenyl-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

• Supported Preyssler Nanoparticles in Synthesis of 1,3-Diaryl-5-Spirohexahydropyrimidines
  作者：Majid M. Heravi、Samaheh Sadjadi、Sodeh Sadjadi、Hossein A. Oskooie、Rahim Hekmat Shoar、Fatemeh F. Bamoharram

  DOI：10.1002/jccs.200900035

  日期：2009.4

  Silica‐supported Preyssler nanoparticles (H14[NaP5W30O110])/SiO2 are used as a new and recyclable catalyst for the preparation of 1,3‐diaryl‐5‐spirohexahydropyrimidines via a one‐pot condensation of anilines, formaldehyde, and cyclohexanone.

  二氧化硅支撑的Preyssler纳米颗粒（H 14 [NaP 5 W 30 O 110 ]）/ SiO 2被用作一种新型可循环使用的催化剂，可通过苯胺的一锅缩合制备1,3-二芳基-5-螺六氢嘧啶，甲醛和环己酮。
• 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
• Dy/chitosan: a highly efficient and recyclable heterogeneous nano catalyst for the synthesis of hexahydropyrimidines in aqueous media
  作者：Nayeem Ahmed、Saima Tarannum、Zeba N. Siddiqui

  DOI：10.1039/c5ra08160b

  日期：——

  Dy(iii)/chitosan as a recyclable and heterogeneous catalyst is used for the sustainable preparation of hexahydropyrimidine derivatives in aqueous media.

  Dy（iii）/壳聚糖作为可回收和杂化催化剂，用于在水性介质中可持续制备六氢嘧啶衍生物。
• 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.